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subscribe@simpleleadership.io to receive the latest updates from this podcast. Hi, I’m your host Christian McCarrick. This is the simple leadership podcast. Welcome back. Today’s guest is Christine Awad. Christine is the director of engineering at Facebook. She joined Facebook six and a half years ago as a software engineer on the Facebook video team, and then transitioned to be an engineering manager, supporting video creator tools.

She led the engineering team for Facebook watch from initial launch to being used by more than 1.2, 5 billion users monthly around the world. She’s currently supporting the engineering team, building video chat in rooms, across messenger, Instagram and Facebook. Originally from Egypt. She went to school there and did an internship at Facebook in 2014 before joining full time. On today’s episode, we discuss the challenges of being a woman leader in technology and how to better support DNI initiatives on your teams. Good morning, Christine. Welcome to the show.

Christine Awad: [00:01:18] Good morning. Thank you for having me.

Christian McCarrick: [00:01:20] Absolutely. How are you doing today?

Christine Awad: [00:01:22] I’m good. How are you doing?

Christian McCarrick: [00:01:23] I’m doing well. It’s Friday. I’m looking forward to the weekend. Where are you calling in from today?

Christine Awad: [00:01:27] New York, California. So I am from my house then.

Christian McCarrick: [00:01:32] Excellent. I think that’s pretty much where we’ve all been for about the last year. Working from home. So as I do with all my guests, Christine, I’d love to have my listeners get to know you a little bit better. If you could just take a minute or two and give me kind of a brief background, sort of how you got to be where you are today.

Christine Awad: [00:01:46] Yeah. So originally I come from, I actually spent first 21 years of my life. There went to school there, studied computer science. Got there. Since I was pretty young, like, I was just like obsessed with like computers.

My dad got me into courses where they like were teaching DUS very when I was really young actually. And then school, they were, it was a new thing in Egypt. Egypt is not like very advanced in computer science, at least at the time. But my school was chosen for like something called like smart school initiative.

So they were actually teaching programming and picking up classes. So I learned. Visual basic C-sharp then C plus, and went into informatics like Olympics, informatics, them books, and then went to college, studied computer science, did some competitions in ECM, so that competitive programming. And then I had a friend of mine who had an internship.

Uh, Google who ended up referring me and I did the internship at Google. Then while I was doing the internship at Google, another friend referred me to Facebook and I actually did that internship at Facebook in the U S and then after I finished school, I got a full-time offer after my internship and came to Facebook and they’ve asked, and this is my only full-time job been here for like 6.6 and a half.

For close, closest seven years versus a software engineer, then a manager then now engineering that active at Facebook.

Christian McCarrick: [00:03:17] Awesome. Congratulations on your journey. It sounds awesome. And one of the things too, you’ve been at Facebook for pretty much, your career started as an IC. How did you get into management? What sort of led you to do that? Was this something you always thought you wanted to do or kind of evolved? Naturally?

Christine Awad: [00:03:31] I actually thought very explicitly that they don’t want to do this. I remember my first couple of years I felt of managers as. Oh, they spent all of their times in meetings and I love just coding all the time.

Why would I be a manager ever? And I remember my manager, like in my a year and a half in or something, I was like the tech leading a big project. And he said, Hey, you actually show really good leadership capabilities. I think he would be a good manager. And I was like, I can do like leadership abilities as an IC.

And I actually still like actually push ICS all the time. Hey, you don’t need to transition to managers. But then my manager went on parental leave for four months and he asked me to like start doing one-on-ones with the team that I was working with. And I was like, Okay. It’s like temporary, but like I used to do one-on-ones anyway.

And we used to spend it talking about the project. What would be so different this time, but it was actually incredibly different. I like, I discovered that people were having like, actually the interesting, crucial conversations with their manager because the manager was not there. And the skip manager at the time was like a VP of engineering.

So like the time he was spending with the team was like once a month. So I was like, basically kind of almost like. Semi manager at the time. And then I hit a few interesting cases. Like I had like a new grad come in and tell me, Hey, like I’d love to know what’s the path from  what’s different. And I was like, Oh, he does, like, from my experience, he does a thing and he does the things to look at.

And then I started seeing this person do this changes and get their way. And I had another colleague at work. She was a female colleague who telling me like, Hey, I feel like sometimes. People unintentionally speak over me in meetings. I don’t know what, how to do it. And I was like, I felt something similar.

And I had this ally who had it in my voice into the conversation. And now I don’t feel this anymore. And I started dating this person for her. And I started seeing like a sense of fulfillment. I would say that I just didn’t expect to have, except from like coding and launching code. And that was. Oh, that’s interesting.

So when my manager came back, I was like, okay, I’m willing to give this a try, but not officially, but like to actually be in that role. And then I discovered also like, okay, I really feel super fulfilled by mentoring people by having these conversations and helping them out. And at the end of the year, I was like looking back at what were my greatest accomplishments.

And it was like, Oh, it was the situations versus the products. That we were launching. So I was like, okay. I mean, it’s not a one way door. So I basically tried it out and of 2016 or beginning of 2017 and it was like, I like it. So I have States since then.

Christian McCarrick: [00:06:12] Great. Yeah. I found a lot of managers that I talk to are sort of the reluctant managers and not a lot of people come in saying I want to be a manager. That’s my career goal. But I think like you, a lot of other people also sort of, there’s some reason maybe a manager leaves and maybe it’s a little bit more temporary slash permanent or someone goes on leave, which is, I think, I think there’s also another great opportunity. The listeners out there, if you’re managing people, if you see that, that you can potentially also have someone go on leave, maybe try to fill in for a role.

And I think that gives them a lot of maybe confidence or other things to even succeed in their IC job, not just their manager job.

Christine Awad: [00:06:44] I agree.

Christian McCarrick: [00:06:45] Great. Now, something else I’ll ask all my guests that transition to management is not always completely seamless. Even today. I continue to make mistakes. We all make mistakes. Any ones that stand out to you that you’ve made protect the innocent, of course, but anything you’ve made that you’ve learned from, or you can help some of the listeners learn from yeah.

Christine Awad: [00:07:02] Numerous mistakes. I think in all levels of relationships, I have made mistakes, especially early on with like people who I support, the mistakes I have made was assuming that everyone is like me. So people will want to be supported the way I’m supported, which is like a classic manager mistake. They went through and I had to actually like learn it the really hard way, but I was like really lucky to have people I support to it, like push back really hard and be like, Hey Christine, this is not Taiwan.

This to like, I would be getting these like messages. I think this was probably the biggest. People mistake. I think the other one is just like, kind of being sometimes forceful in advice based on experience. Like when I feel like someone is like me is someone who has similar career trajectory or really hard and specific thing I would like to be giving them, Hey, you will burn out.

Watch out. And I remember in my days, I was like used to like, when my managers come to me and tell me this, I’d be like, why are you saying like, we are very different people. Why are you giving me advice in this specific way? And I made this mistake of doing good the same way as well. Interesting. But I think the biggest mistakes beyond on supporting people on my, with my peers and everything else is that I just didn’t realize that like, Being the manager.

It starts to also have a specific weight when you start having a specific feedback in conversations. So I used to, like, I also joined Facebook very young. It didn’t have, let’s say the mistakes that you make of like, just being, I’m an engineer. And I want to just execute in this thing and I have never been an engineer before and someone is blocking me.

So this person is a blocker and considering like specific functions of blockers, et cetera, was like one of the things that like I hit. And honestly, I didn’t see it back then this way, but I feel like now it’s like blessed by the fact that I had managers who very explicitly had a high bar on this and blocked my promotions a couple of times to actually teach a lesson that yes, you can be like amazing at execution.

You can like bulldozer your way, whatever way you want to. But if you don’t build the. Relationships and bring people along and be a true leader on the team. Then you will never be successful and people wouldn’t not want to work with you. And if people don’t want to work with you, then what’s the point.

Christian McCarrick: [00:09:19] That’s right. Yeah. No, thank you. I thank you for being candid with that. I appreciate it. I think I just do this. I’d ask these questions too, because sometimes I think especially first time managers. They get the sense that they have to be perfect right from the start. And that’s not true. We all make mistakes, but like you said, it’s important to have that introspective to be able to look and learn and then to improve over time.

So thank you for that. One of the things too, I think we often focus these shows on one topic and the topic we’re gonna focus. Our conversation today on is going to be around diversity inclusion in tech, specifically women in tech. And I do thank you, Christine, for coming on and agreeing to talk candidly about this is critical yet I think challenging topics. So thank you for that. I do want to start off with some statistics. According to Pew research thing today, women make up about 46% of the overall workforce in the U S yet only about 14% are in software engineering, slightly higher in the larger sort of computer related fields.

3% of computing related jobs are held by African-American women. 6% held the Asian women and 2% by Hispanic women, 50% of women say that experienced gender discrimination at work. And in 2016, women only received about 2% of total investor funding and women led businesses made up just 4.9% of all VC backed deals.

So, as I mentioned this, and I don’t think these stats are anything new to you, Christine. I mean, what are your thoughts when you hear stats like this, how does it affect you? How does being a woman in tech kind of shaped your experience?

Christine Awad: [00:10:35] Yeah. So it’s an interesting topic in gender. The stats are sobering. Like we, it seems like also almost every year, while there is some progress, the progress is just so much slower than what we were hoping for. I think when people like ask me this and say, Hey, what are the reasons? And then even if you end up like digging deeper, if you look into the workforce and computer science, Even in like companies that push for diversity and really cared about diversity so much like Facebook, the percentage of women who are in like entry-level jobs since I’ve taught engineering is very different than women in like leadership level and beyond how a lot of people think, okay, is it like, how do we fix it by courses of like discrimination?

We think through like managing bias, managing inclusion, we have classes in Facebook, like be the ally, which are all like, actually a really good. And I think how a lot, and I have seen like people go through them and then think, Oh, I actually was doing this action. And I discovered this right now. But I think it also comes from just seeing people in the room around you who look like you as a woman in tech.

One of the things that I was like, kind of blessed buys, it’s like, actually, when I have other women in the room, they send me sometimes screenshots of like, Hey, here it is this like meeting group right now. It’s like, it has 30 managers and only two are women. Or there is no black men or women in the room.

So I do think the situation is hard for me, how it affected me personally is probably two things, which is probably different than how it would affect other women. But some women do it the same way is it kind of made me more ambitious in a way, which is like the front is like, I took it as a challenge of when I was very young.

I don’t know if this happens and they last or not, but back in Egypt, one of the things I was always the first in class in math. Mathematics. And I used to like, get the feedback from other boys at school of like, Oh, it’s very weird that you are a girl and that you like math and you were like, good, that’s it.

And I was like, I saw this as like a challenge of like, okay, then I will be better at math again, to be good at it. And I took it the same way in like computer science. But then now when I feel like I’m the only person in the room, I’m like, okay, I’m going to be a reason why people believe that, like women can do it and do it more, which I understand this actually like when you talk to people from underrepresented community, some people will feel this way.

And some people feel like this is a huge burden on them as well. So like, I’m not saying that this is the angle, but this is how it affected me. And I think the other thing is like I started being very insistent on being an ally. Two people. So I am in rooms where I’m the only woman in the room and I am in rooms where people discuss opportunities for other, like, we have an opening for an engineering manager role where we have an opening for someone to join leadership.

Who do we consider? So I start seeing, Hey, this person like being like a sponsor for others. Women to be there, or I’m in a room when performance management is described. And then if I end up seeing any example where I would say what I feel like we’re promoting this person, he has been expecting it. And I’m like, okay, who are the other women who probably haven’t talked to you about this?

So like, if you start seeing things that are not explicitly like intentional bias, but you start watching it’s out and this is how. It has affected me and how I’m trying to like pay back. And then finally, just the thing that I cared about the most on diversity is like, I do think there is a ton of work that we can do on finding women who apply.

But I think also people apply when they see examples of them. So the thing that I’ve been focusing on is women who are already in the company. What I see a lot of potential in them, how can like. I provide them with a mentorship, similar to how people like mentored me and were the allies for me and sponsored me.

Christian McCarrick: [00:14:26] Sure. No, thank you for sharing. I appreciate that. But you’ve mentioned in that a couple of things from early on, you’ve mentioned a couple of things you’ve seen around, maybe some unintentional bias. Are you comfortable sharing any negative experiences or challenges you’ve experienced or other you’ve experienced happened to other women in tech that maybe are a little more blatant or maybe not so blatant.

And I think those, sometimes those are the important things to let some of the listeners hear, especially some of the men listeners here that might not understand that this is a behavior that is actually hurtful harmful in some way to women in tech.

Christine Awad: [00:14:57] I think an example that I faced personally, and I have seen a couple of women face says being described as aggressive and because of being aggressive listed as, okay, this person like Christine was aggressive in the situation.

So she was not bringing people along. And why there is feedback there that is valid around. How do you should everyone should push people, bring people along? I think in other cases, I have seen men being described as effective in them or not getting the feedback as much. And I think how it has affected me is that I got to face where I call it out.

Sometimes I’m like, Things like, I don’t want, because I’m a woman to get a pass on, not bringing people along. So like, first of all, like I acknowledge that this is a good feedback and what I’m doing to do it, but then it’d be like, okay, every single person should watch out for their biases. And also watch out for the other people, biases around them.

And the fact is like, as women, we are expected to be like nicer than we are expected to be bringing people along. Even if you feel like don’t mention it as much. And when I get feedback like this, I actually kind of push people to be like, okay, maybe do go to like. Managing pious classes and watch out for it.

And then when I am in the person, who’s actually running meetings and I see feedback where, when we talk about men, we talk a lot about the accomplishments and the things that they have actually like what was the result? Of their behavior. And when we talk about women, we talk about behavior more than the results I like, I watch out for it.

And so these were examples that I had, honestly, in more recent years, I have seen this behavior improve and I have seen like other people calling it out other than me in the room. So like, I was really actually delighted. We just went through mid cycle calibrations of. Like high level ICS promotion and high level manager promotion.

And I’ve seen other people, other men in the room who are allies who, when something like this was described, I didn’t have to be the person who was like calling this out in a meeting. I was like, okay, this is actually amazing progress. I’m so glad. Oh, your classes are working. No, no, no. That’s good. That’s great to hear too.

Christian McCarrick: [00:17:12] I think it’s fantastic. And it’s one of the reasons I joined. I think Facebook and just candidly, I think one of the things, as you mentioned, calibrations, and I do feel that clearly there’s room for improvement continually in every org, no matter where you are. And I think we do take that feedback, but I think the level of hopefully quantitative type analysis that we do and try to leveling the playing field and trying to be fair across the board, compared to other companies, I have seen that we do actually a fairly good job. Not always room for improvement. Right. But I think comparatively, I think we do take it seriously with the trainings and just, I’ve seen even the last half people sort of calling people out, even when it’s just men in the room and there weren’t any women, which is a problem in itself, but I have found that starting to happen more to where you start seeing people say, no, are we labeling that because of this or that? Let’s actually go deeper on that. So definitely good.

Christine Awad: [00:17:58] Yeah. And honestly, I think I’m an example of this. Like I tell people this all the time, I had a really good career at Facebook and a lot of it is because I also had managers who, by the way, you weren’t old men who pushed for me so much. And actually, like I had a manager, I don’t know if we can call names, but like my previous manager in my team was the person who, when I actually went to him with questions on, Hey, like just like watch out.

I wasn’t this like. Conversation. And I think I could be described as aggressive in it. He was like, you’re learning. I’m actually, I don’t want like any biases to be there. And there are a lot of things that make you and make you really good at what you do. And I think the biggest part is that you’re effective.

You cut through random stuff and just go to the point. And I think this is what is unique and why. Oldest one to be on my team. And I don’t want you to lose the skill like you should watch out for where there are sharp edges and like things where there is negatives out of this, but you’re unique. And I wanted to be on this and I don’t want you to be like, apologetic about it.

And I was like, okay, I could work for this manager all my life. And this are actually like, A lot of my managers in Facebook were like this and they were my strongest allies. And right now I see things where we like expect all of our managers to go through like managing inclusion, be the ally managing bias and a lot of classes that we just actually have at Facebook. And we’re like expecting also I see, is to start going through it and I’m starting really to see like a lot of progress and people who really care about it, not just like lip servicing, that we are actually really absolutely believe that this is the right thing to do.

Christian McCarrick: [00:19:41] And this actually, I think segues nice to another topic, which is kind of sometimes can be contradictory to the being seen being as aggressive, et cetera.

And that sort of like the topic of imposter syndrome, I think. Unfortunately, Harvard study women often are not confident or underestimate their skills reports. Show that female computer science graduates with eight. Years of programming experience, put themselves down as confident in their skills as their male peers with zero to one years of experience.

Right. So one, have you ever experienced this yourself? And if so, so, you know, how did you sort of go about handling that and especially. If you want to become overconfident, then sometimes you get labeled as aggressive and it’s this back and forth. Right? How have you found that balance and how have you gone through that?

So

Christine Awad: [00:20:24] I have seen it happen most of the times, especially with other women on the team.

I have seen examples where someone would like, I would go to someone and tell them, Hey, here’s an amazing shop for you. Apply for it. And they’re like, No. They said that lucky the center expectations of the job and I’m like nine out of 10 of them. So I’m not like doing it. And I, like, I have seen the other people who apply are way more qualified.

So I like, see definitely the Harvard study is right. And there are like lots of examples of it. I think it goes from having honestly people around you who lift you up, like the Fiji CMO who’s the head of Facebook app says something that I keep telling people. She said that the thing that she looks at when she works on something, or when she’s like, considering the shop does like, who is her manager and does her manager see the metric in her?

Because she talks through that. If the person who was your manager, or, the orders, people who are around, do you see the magic in you, then they uplift you. Then when you’re like pushing yourself down, they’re like pushing you up as well. And then hopefully over time, you don’t need people around you to be pushing you.

But I do think like that job of like being like someone’s cheerleader is more needed for people who face imposter syndrome. And by the way, it’s not just women, like lots of people face this. So like, this is not many. My biggest advice is like, I tell people, Hey, like, Actually, this job is interesting. It’s an interesting product and everything, but the biggest bonus is this manager or this team is actually known to be like pretty strong allies.

And I have seen it and I have seen this happen and I have been like trying to push other women who are in roles where they can actually be sponsoring other people to be like, okay, don’t just wait for who are coming to you for the job. Consider other people who might be qualified or not coming and go wide in the train for me.

Did I face imposter syndrome myself? A ton of times. I think at the beginning, when I just joined Facebook, I was just like, okay. I came out of school, I’m working at Facebook. My school in Egypt is not like a well-known school. It’s like, and I’m faced with like, All of these people who come from like best colleges in computer science in the world.

And I was like, I didn’t know if I was good enough. And I had a manager at a time where I really love this manager now. And he’s actually the person who grew me the most in my career, but he was the first time he was supporting a team. And his style is he was managing people. Like he wants to be managed.

And his style was okay, I’m going to mention what is missing in something, because this is the best way to, to improve is if you know what is missing versus here’s how great you are. And I think in his mind, I was great in so many things, but then in every single conversation it was, Hey, here’s the thing that’s missing in this project.

And I was facing the worst imposter syndrome ever. So it climax to the point where I was like, we’re in a deadline, in a project. And I was like, I just like lost it. I was like, I’m really horrible at my job. I don’t know what I’m doing wrong. Like, I just couldn’t do it. And he’s like, what are you doing?

What are you saying? This doesn’t make any sense at all. You’re amazing at what you’re doing. And I’m like, but do you all have our one-on-ones you’re telling you everything that’s missing. And he’s like, Oh, it’s just like how you grow, but you’re really good. And I was like, Oh, Okay. And then I was like, okay, maybe he just told me this.

Cause I was like, feeling really bad at the moment. And then, um, at the end of the tough, I actually got to redefine expectations, which is the highest speed thing that like we have at Facebook. And I was like, how do you like this? I didn’t get the signal at all. And I think afterwards he got tested where he’s like, Oh, he starts the meetings.

He does everything that’s going good. But I have learned afterwards to also do this, which is like interesting, but. Yes, people face imposter syndrome and it’s around. How do people like lift them up or own? And I think the biggest thing I tell people who face this is like, Hey, no, that you’re good. The fact that you are working in these companies, the fact that you’re here is.

By itself proof it you’re good. And you’re actually like qualified to do the next thing. And what is the worst thing that can happen by you applying? Like the worst thing is luck to you. You get rejected and you are in the same place that you are, which is if you don’t apply is where you are right now. So like, just like apply because the upside is so much higher.

Christian McCarrick: [00:24:54] Those are great background. Great anecdotes. I appreciate sharing that. My listeners certainly can appreciate some of those stories. And that’s good. I think it’s good feedback for some, our listeners to maybe be a little bit more forward or proactive with asking some of the people that you support, what is their feedback style?

How do they like to get it so that maybe they can avoid some of these conversations or these surprises at the end later? Right? I think it’s always certainly good. Some people have mentioned the past, coming up with a manager contract or something. This is how I manage. This is how I do, this is my expectations of me.

Then they give it to kind of new employees. It’s something I know other managers at other companies do as well. Right. They try to set those expectations appropriately. I want to move on to sort of something that’s timely right now. And the specific impacts that COVID has had on women in the workplace, specifically women with families in the workplace and as last year, Alone 1.2 million parents exited the workforce with a staggering three quarters of those people actually being women.

Now, majority of listeners on this podcast to engineering managers, what are some of the things right now that engineering managers or other people can do to try to address this problem we have?

Christine Awad: [00:25:54] Yeah. I think the biggest thing is knowing that all of the policies that we had before COVID, doesn’t apply after COVID whatever, like sick leave, flexible work.

Things that you had is like, was never tested in a pandemic where like people are actually staying at home and doing what they need to do. And I think being flexible is the way to go and realizing that people need flexibility in different ways. So one of the things that I been really grateful at Facebook is that like, Facebook has COVID leave, which everyone.

Who is a parent can take for as long as they want to. And it’s still ongoing I’m until now. And I have had so many patterns who have been like, really thankful about this, because it just gives them the chance of whether they want it to be a week or a month or two months or two days a week, or whatever that they need to just like, make sure that they’re taking care of their kids and taking care of their sanity during all of this matches of time.

I think the second thing is just. Flexible hours. The only thing to watch out for is I had a patent in my team before who was a woman who was doing musically, just trying to do it all, but with flexible hours. So she was basically trying to, like she was saying, Hey, between this hours and this hours, I can do any meetings, but she’s still trying to work eight hours plus a day.

Outside of these like working hours. So she would like put her kids to sleep and then like work from like [8:00] PM till like 12 and then wake up at like six before anyone is like sleep and like try to work from like six to like nine and then take care of the kids. I mean, you can probably do it for a week and then feel horrible afterwards.

This is just like not sustainable. And I think the biggest thing that managers. Can do and we’re doing, and I did at the time, it was like, Hey, no, this is not possible. Like take COVID live. It’s the thing is that we need to watch out for is a lot of women who specially work on computer science and art in this industry.

They are there because they push themselves. They went against like a lot of odds to be here. So they don’t need other people to push on them. They are like pushing it. So that lots of the time, my job as a manager is to actually tell them not to realize that we are in a completely unexpected time. The fact that they can’t.

Cope with all of this is not a failure by any means. It means just that they are human and he disposed of the expectation that’s happening. And it’s fine to take it easy for a half or a year on your career, because life is just the most important thing right now versus a career. And this is not setting them.

Back. This is not like, okay, now you’re losing your job or your life not meeting expectations or anything like this. We have things like, which is, I think Facebook has been really good at is listing, adjust, adjusted expectations for the half. So beyond all of the leaves, you can decide with your manager, what you can achieve.

This half, and this is how you are evaluated on versus what are the normal expectations of your level. And I think these are the kinds of policies that all workplaces need to adopt during specialty COVID to make sure that when we get out of this pandemic, we have workforce, which is actually ready. To innovate and get back into like full mode versus you end up with a situation which is so much worse than diversity, and then spend years trying to undo the damage that like the pandemic.

Christian McCarrick: [00:29:27] Yup. And I do want to have an explicit call out to any of my managers out here as well, or any of the people who are listening that are also. Partners in relationships that are men or partners relationships. I think this is an interesting time of year. I know we’ve school is potentially getting out whatever form of school you were doing.

I think a lot of women tend to take the burdens of things that you don’t see, like planning for summer camps, things like this that just sort of are the silent tasks that add up a lot of time and energy. Just take some of these off, but you might not even know about them. And I think some of these minor micro things that kind of add up, so I do challenge everyone out here who’s a leader or just an IC listening to this that is, that does have a partner that might take on these burdens and responsibilities more, please, especially during this time, but why not every forever moving forward, this is a good opportunity to try to help out in areas that you might not have done the past.

Two things two, I want to mention really quickly, you were talking about some of the things Christine, that Facebook has. We do have two programs two right now that I want to kind of let people know about the Facebook as a returned to work program. If anyone has been out of the workforce for a while and is hesitant to get back, maybe again, some of that imposter syndrome or made it lack of confidence, but we do have a 16 week program to help with the transition providing coaching guidance, experiencing working in real teams and real challenges.

You go to Facebook, careers and search for return to work that will pop up. And that’s one of the programs. The second one, too, this is the accelerator program, and it’s a goal to partner candidates with women in tech that are at Facebook to help amplify women’s voices in the workplace. These are opportunities to chat with people like Christine or some others.

If you’re thinking about going through the interview process, hopefully it can maybe demystify that a little bit as well. So you can actually contact, accelerate her@facebook.com to find out more information about that. Something Christine, as we move on, you’ve mentioned this a couple of times. Support systems.

I think they’re so important for every engineering leader. No matter what I think the higher you go to it gets kind of lonely, but even more. So I think for leaders from underrepresented groups, how important was this sort of support ally group sort of thing for you in your career? Super important. And it has been at all levels.

Christine Awad: [00:31:24] Honestly, when I was an engineer, like one of my closest friends at work who used to be at a colleague of mine at my first team was actually my support system. When I was like, thinking about what is the next thing that I would do in my career. He was actually the first person who called me down and my first.

Break down its work. What I was thinking that I was just like doing a horrible job and he was the one that’s like, no, I have been in the industry for a very long time. I can tell you’re doing a good job. And just like having someone like him at that point just told me, okay, I’m not gonna quit and just leave because here’s someone who is that for me afterwards, it was a class of like managers who really were like my support systems in a lot of time.

And also who connected me with other mentors throughout. The organizations who I would, can have an honest conversation with and learn from them. And they had no other agenda except what is good for me to do. And now, I mean, I talk about Fiji a lot, but Fiji is the person which is she’s. So amazing. So busy, it’s so many things and she finds time for people.

Whenever, like I sent her an email, I know that an hour later she’s like sending me a message of like, Hey, like actually jump on a call for like five minutes or 10 minutes and talk through this. And it tells me like, think through, okay, here’s how I should be thinking about this problem. And. Honestly, it tells me that I have people in the company and people around me in general, who cared about me and it makes me a lot more invested in the company and more invested in just my career and more invested in me as a person and how I’m like I should be pushing things forward.

And I think what I try to do is also try to. See when I see underrepresented groups, whether it’s like women or like, Oh, that’s an ends or like blacks or any, like, African-Americans like in general, like any group that’s like under represented in tech, which we actually have a lot of like groups like this in Facebook.

I try to like push on, Hey, who is your support system? And even like people who don’t belong in any of these underrepresented groups, if you don’t have a support system around you at work, You’re very likely to end up in a situation where you need to talk to someone about something and then feeling like you don’t have anyone to talk to you about.

And when you are in a down situation, you don’t want anything that keeps you a bit down or push you more down. So this is. What I try to do. And then finally, one of the things that I really like at Facebook, which has been working for me, but not another, like a super personal level, but I check it out every now and then we have this internal groups.

Yeah, Facebook it’s like women at Facebook black at Facebook, Latinas at Facebook pride at Facebook. And sometimes when I actually feel annoyed about something, I just like go on and post that or see what’s happening on the post then. And then I start seeing this like incredible group of people who are just like, not judging you or anything, just like we’re here to support you.

And I think these kinds of support systems, especially in normal time method and especially in hard times, like what we’re passing through right now matters significantly. Yeah, no. Awesome. Thank you for that. And I agree, no matter where you are, what level having a support network has gotten me through, whether it’s an individual or some peers or a group that I can talk to.

Christian McCarrick: [00:34:44] It’s why I actually started this podcast. I always called it my hour long support therapy session when I could talk to other leaders to make sure I wasn’t totally screwing up. And cause I’ve had imposter syndrome too. Like I said, it happens to everybody. One of the things I want to, as we kind of. Get on here in this conversation.

One of the things I think happens is a lot of potential candidates, especially from underrepresented groups are intimidated by Facebook or any tech company really is interview process. Right. What advice would you give to potential candidates to encourage them to apply and how best to prepare for that interview?

Christine Awad: [00:35:15] I think in general, like I would tell them, just apply, get over the intimidation and apply. Like you will learn from the interview process in . And the fact is like tech companies are trying to hire significantly and there are a lot less people applying than we want for jobs. So like, there is a place for you.

The second is. Depending on your discipline. I would, I prepare, like I would look into like, what are the kinds of interviews? There’s so many sources online on this. I would have a friend look over my CV. I’m actually happy. People want to even just like on LinkedIn, send me like reach outs of here’s my CV.

Do you want feedback? I’m happy to like go over to this for like people who are applying for the management jobs or software engineering jobs. I think you’re underestimating. How many people care about getting you in that? Like, people will be happy to like offer advice. And then I tried to get someone to like, do a mock interview for me and just give me some tips on, okay.

Here is like you maybe talk too much in this example or you talk too little or you’re like, Don’t go into details on this example so much, or watch out that you take so much longer time or less time than you should think that it’s just like some tactical things that help. And then if I’m also still like, worried about what are the next steps, if I’m like in the interview process, I would actually tell the recruiter, Hey, like I’d love to talk to someone who can be an ADI and be second diffuse.

And I can ask them some questions I have. I actually had. Multiple talks where like recruiters reach out to me and tell me, Hey, like I have this person who is just like, worried about what would be the interview process for like engineering management. And can you just like spend that 30 minutes, 45 minutes answering their questions?

And I’m always like, happy to take it. Then there are so many managers in Facebook are happy to do this. The first step is just apply. Second is like, look online on like what materials are available, reach out to friends or any people that want to look up your CV. And if you don’t have any of this group, just pick up a couple of people in the company from like LinkedIn and send them, Hey, like here’s the thing I’m applying.

I’d love to get feedback on this. And likely one of these people that you reach out to will like reply back, especially if it’s like a. A small task. And then once you’re in with a recruiter, tell them, Hey, I would love to actually get someone in the company to talk to me about some examples. Like the routers are really helpful, especially like in Facebook actually like shout out or recruiting team.

They actually definitely have, do we choose Facebook and the end? And they are like really incentivized to help you. And this would be the next steps I would do. Yeah, I agree. Double shout out. I think we’re just looking for ways to say yes, right? I mean, we’re not trying to find no. Right. We’re trying to find every way we can to get you.

Christian McCarrick: [00:37:56] Yes. And similar to Christine, feel free to reach out to me. I’ll be happy to give you some tips on interviewing. I think the thing you called out with doing a mock interview with somebody is so important. Sometimes we don’t feel vulnerable enough. We’d rather say this to a stranger for the first time, instead of a trusted friend that that can really make all the difference.

I did that I’ve been in industry for a long time. And it turned out, the friend I used was grilled me way harder than anyone else ever did. So when I entered the interview, it was like, that’s it? Not that it was easy, but I felt really prepared. Right. Did you give me that confidence? So that was awesome.

And as you mentioned that our programs reach out to the recruiter, there’s a whole program at Facebook where different people will be more than happy to help you for some coaching interview prep, or just saying how Facebook is treated them. And I think it’s certainly worthwhile. So thanks for pointing those out, Christine.

One thing as we wrap up, I always ask any kind of the guests on the show, any recommendations you have for like a book you’ve read recently or something that was like really stuck in your memory or a podcast or video or anything like that, that you might recommend to engineering managers?

Christine Awad: [00:38:52] Yeah. I think one that I really loved that I read recently is the score takes care of itself.

Christian McCarrick: [00:38:58] Oh, look at that. It’s having on my bookshelf.

Christine Awad: [00:39:03] I think honestly, probably whether it’s like an ICU or an engineering manager or anyone in any industry. Like, I actually think it’s a great book to read. I think it pushes a lot on and doing the thing and things will take care of itself, a method and like focusing on like less politics, less anything, and just like.

What’s that I think to do, which I think the author just like nailed it and the book and I really enjoyed it. And it had really good examples that can apply to any leadership role whatsoever. So this was like probably my favorite book recently.

Christian McCarrick: [00:39:34] Awesome. And I’ll second that as well, great choice in early, that’s an awesome book.

As we wrap up, what’s the best way. If anyone wanted to get in contact you and he’s socially willing to share LinkedIn, something like that.

Christine Awad: [00:39:44] Yeah. So I am happy to share like my LinkedIn, like please like reach out to me through LinkedIn is probably the best way. Yeah. I’m also available on Facebook. Like if you searched Christina, other probably will like come up and I can reply with probably LinkedIn is what I follow on the most.

Christian McCarrick: [00:39:58] Awesome. Well, and for, again, as a reminder to all the listeners, any of the books, we talked about links to any programs I’ve mentioned, they will be on the show notes@simpleleadership.io. Christine, I know you’re busy, a lot of planning starting to happen at Facebook too and mid cycle. So I super appreciated the conversation, had a great time.

Christine Awad: [00:40:16] And thank you very much. I’m really happy that I chatted with you. Thank you so much for having me. I really also had a great time. Thank you so much. Great have a nice day. Thank you.

Christian McCarrick: [00:40:24] Thank you for listening to this episode of the simper leadership podcast, hosted by me, Christian McCarrick. If you have enjoyed the show, please subscribe and don’t forget to leave a review on iTunes, full show notes and additional information can be found on simple leadership.io.

If you knew someone who would be a great guest for the show, or you want to share your own experiences, please drop me a line. We’ll see you back next week. For more technology, leadership tips and advice. As I interview more top software engineering.

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Christian McCarrick: [00:00:31] Good afternoon, Ashish. Welcome to the show.

Ashish Aggarwal: [00:00:33] Thank you.

Christian McCarrick: [00:00:34] Yeah, absolutely. And I’m glad that we have not met before, and I’m super happy to have this conversation with you today.

I’ve been looking forward   to it for a few days after kind of researching and prepping and looking at your background. I think we’re going to have a great show and lots to talk about today.

Ashish Aggarwal: [00:00:46] I am glad you feel that way looking forward to it. Okay, excellent.

Christian McCarrick: [00:00:50] And where are you connecting from today Ashish?

I am in Palo

Alto.

Okay, good. Yeah. I’m in the East Bay area. So fairly clear skies today and we’ve been having some smoke and issues. So it’s a nice warm sort of fall day here in the San Francisco Bay area.So great.

Absolutely.

Ashish Aggarwal: [00:01:04] And we are all very glad to see clear skies now.

Christian McCarrick: [00:01:06] Yes. Yes. You can get very meta about that statement, but physically, at least right now. Yes. Clear skies. As I ask a lot of my guests. If you could just give my listeners a little bit of context and background, basically how you got to be where you are today.

Ashish Aggarwal: [00:01:20] Sure. I am currently the co-founder and CTO at productive. We started this company two and a half years ago, currently about 50 people total in Palo Alto headquarters in Palo Alto.

Before this I’ll just go in reverse sequence here. I was the head of engineering or VP of engineering for Postmates. Postmates is on demand food delivery company. I hope you, and many of your listeners customers recently, it was acquired by Uber, but I was there for approximately two years. In San Francisco.

I had a great time there. We can talk more about it later. Yeah. Before that I was the director of engineering for Amazon in Seattle. My teams were spread across three countries, you know, us, Canada, and India, but I was personally based in Seattle building a logistics software technology for Amazon to move their freight.

The big trucks that you see on the highway with Amazon prime on the side. My team is partially to blame for those, or at least that technology part of those. And a couple more things before that, my brother, my first gig in e-commerce was at eBay. I was a director of engineering. They’re building a again, technology for their shopping cart, checkout, data analytics, those kinds of things.

It was an amazing experience with what hundreds of more than a hundred million customers. That Eva was handling at that time. And I spent a lot of time at Microsoft before that I spent about 13 years actually at Microsoft building enterprise products for them, the latest, I guess, reincarnation of what I worked on is called Microsoft teams or Skype for business before this, that you might’ve heard in audio video conference and chatting product. I was in some sense, the first engineer on that whole area, back in 99, when I joined they kind of said, Hey, we don’t know what exactly we’ll build, but here start exploring something. And I was feeling obviously junior back then, and still are a lot of stories to tell from Microsoft.

And a lot of my career learning and in sometimes growth as we call it happened there from a engineer to a senior engineer, to a lead and to manage it and indirect and so forth. Well, that’s kind of me. I am an engineer from education and throughout my career, I haven’t switched. But that’s my journey from Microsoft to eBay, to Amazon, to Postmates, to productive now.

Christian McCarrick: [00:03:42] Great. And a great kind of journey. I think it is taking into where you are today. So thank you for sharing that you did touch upon one thing, which I always ask a lot of my guests is. And you said it’s sort of happened at Microsoft. What was that transition from that lead or the IC role into manager like for you? Was it sudden, was it planned? How did that go for you?

Ashish Aggarwal: [00:03:59] It was actually, I don’t want to say natural, but it was almost smooth in some sense, right. There was not like a step function and the way it happened really was, and I thanked my leaders and Microsoft for doing this in this fashion. Is, I was an engineer, turned out I was a good engineer.

And so eventually when more junior engineers joined the team, I started looking over their work and guiding their work to make sure it’s to my standards or just watching them. And so I became the senior engineer for a few people. Yup. And then soon enough, they said, well, why don’t you formally kind of become a tech lead for this was like, in the sense that we will hold you accountable for the quality and the completion of the work in a given time.

And because I was working so much with these engineers, When the time came to kind of write the performance reviews and when the time came for them to kind of say, “Hey, how do we grow into our career to become a better engineer in both sides?” They were talking to me, but the engineers were talking to me as well as their managers are talking to me to get performance feedback.

And then one fine day, somebody said, “Well, it looks like you are going to be their people manager. You might as well take the title”. Oh, can you do this assertion? There was no scare factor in sometimes I was already doing the job. Yeah. And that’s when one of my senior leaders kind of said, “Hey, this is really the best way that I don’t have to anoint you” kind of, as the cliche goes, leaders are not anointed.

Leaders are formed when they are around people that are following them. Since I had followers, I was a leader and leader and people manager are two different things. I understand that. But in that people management, I already had direct reports. They were just not on paper. And so the formalization was smooth in that sense.

Yeah, no,

Christian McCarrick: [00:05:47] that’s good. Yeah. And it’s always interesting to hear the origination stories of how people and they went from that IC role and how they got into the manager role. And it’s kind of part of why I do this podcast to show a little bit too, that there’s lots of different paths to get there. Lots of different paths to starting a company, to be co-founders, to be leaders, to be VP of engineering’s and it’s however you get there.

I think it’s interesting for people to understand that what it looks like for one person, it might not be the same for another, and we all can get there through varied paths. Right. So thank you for that. Yep. Um, one of the things also is, and it doesn’t have to be at your first job, but over the many years now that you’ve been managing and leading teams, any mistakes, you make that point out that might’ve been sort of a learning lesson for you or for that other managers also might learn from.

Ashish Aggarwal: [00:06:30] Oh, boy, this is an interesting question because I’ve made a lot of mistakes, right? And I, yes, I’ve had a lot of success stories. Sometimes we talk more about them, but mistakes is what you learn from, and that’s how you really grow. And I’ve been doing this for a long time. At least the people management part of it for, I would say a good 15, maybe more years.

What are the mistakes that people can learn from? Let’s go couple of, maybe these are obvious things, but let’s, let’s see them right. Army manager. I made the typical mistake of not letting go, not actually trusting my team to take control. I was still this, Oh, you know what? This is me. I’m accountable for the whole thing.

My team is my helpers. I am still the smartest person in the room. And that was obviously not true. I was actually very lucky that my team was really, really capable junior that’s. Okay. But the collective capability obviously was much, much higher. Right. Everything had to go through me and she was interviewing every document for the last line of the design to every line of code to testing it himself.

Everything was because I was like, Hey, it’s my ass on the line in some sense. And then I don’t remember exactly who said it, but variety of my team and my superiors, my coaches told me, you know, your team can run much, much faster than this, and we understand you’re new, but letting go and understand it’s hard, but try it.

Why don’t you try it to save space, see what your team does. If you just let them be, just give them the problem and let them come with the solution. And they might surprise you. And I started doing that and, oh boy, that was eye opening. And from then on I have learned this. And unfortunately I did not have to be a large cost in this lesson because this was early days and there were supportive people around me.

But I will say that is something that I see a lot of new managers do at any level. Right. It’s not just when you go from an IC to a manager with the same thing, when you manage it to a manager of managers or VP or whatever, Letting go saying, “Hey, I will let my team solve this problem, even though I have good ideas about it, I can give input, but let me give up control.”

So I think that is one mistake that I see a lot of managers make everywhere, small companies, big companies, different levels.

Christian McCarrick: [00:08:46] Definitely.

Ashish Aggarwal: [00:08:47] Yeah. If I may share one or two more, the other part is about team building, right? And again, these are known things in the industry, you know, it’s better to hire one A-player than two C players.

And again, I have done that sometimes without knowing it, but then after I have done it, I realized later on how to distinct was sometimes I was, I just got frustrated with, because there was a position open for so long. I was like, let me just get somebody in here. It’s okay. If they’re a C player, I know it, but let me just kind of get things started right on the Workfront. And then I had to pay the price later on. They were not happy. They did not gel with the team of A-players and so on, so forth. And then eventually they had to go. And that was a painful, painful breakup in every case that has happened. So if your team is of A-players and your philosophy is to hire A-players and I’m watching this, the only thing that everybody should have, there are circumstances and different needs, but.

If your philosophy is to hire A-players, then take the time, hire the players. It takes time. You will have to be patient. Anytime I lost patience, it was a mistake and I paid for it. And similarly on the flip of it is when you know somebody’s not the right fit for the job. You know what, don’t drag it out. I dragged it out a couple of times.

Obviously there are situations where there is a temporary thing and can be turned around and those help. But my mistake was even when I knew that him and this person is not the right fit for this job, they will be probably a better fit for some other job in another team or with another role or another company for that matter.

I knew it. I honestly knew that it’s only a matter of time before I’ll have to pull the plug, but I just didn’t because I was uncomfortable. It was hard to give that message. There was confrontation. I was avoiding that. And again, it took some coaching from my superiors. This part actually gets harder as you grow because the person you’re sending the message to is usually more senior.

Christian McCarrick: [00:10:52] Yeah, exactly.

Ashish Aggarwal: [00:10:53] And the key thing you need is, is the support and a safe space from people around you, your peers and your managers to say, “Go ahead, make the decision.” It’s okay to have tough conversations. It is actually going to be good for both the company and the person concerned,

Christian McCarrick: [00:11:07] RIght. And the team itself.

Ashish Aggarwal: [00:11:09] Right.

Christian McCarrick: [00:11:10] You know, that’s another thing because it starts off with the one hard conversation. But if you lead, let it drag along enough, it can turn into five or six hard conversations and your team might lose some of that trust. And I like what you said though. That resonates with me. It sort of by the time, you know, like if you have something, if you have an inkling even do managing for a little while, like clearly you want to look and investigate all of the reasons to make sure there’s no snap judgment of, is there any bias or anything, but usually I think it is true that if you have something, you know, then it’s at least worth that conversation it’s at least worth diving into and sooner rather than later.

Right. So, yeah.

Ashish Aggarwal: [00:11:44] Absolutely. Absolutely. So those are the three mistakes that I can relate. There are actually a lot more, but let me pause it.

Christian McCarrick: [00:11:51] Absolutely. And that’s good for that. I appreciate those. We all make mistakes. I know it’s usually just which one of the many ones that we choose from, but like you mentioned, also the mistakes are opportunities to learn and that’s kind of why I do the show and why I have experienced tech leaders like yourself on to kind of help guide those maybe are not as senior or even there are a senior, but we still can all learn from each other.

One of the things that I want to talk to you about and kind of spend the rest of the time when the show is talking about something that I think you’re passionate about engineering your teams for impact and focusing a little bit, why that should be your team should be focused on the marathon and not the sprint.

And one of the things I want to start with this is. Let’s start with the vision of what good looks like. So if you could help me paint an ideal picture for my listeners, what does a well-rounded high performing team look like? Like how do you know that if you see one?

Ashish Aggarwal: [00:12:38] I have seen high performing teams work with me and around me. There are a few characteristics that show up and they’re all interrelated, but I can tell you what things show up. The obvious thing that shows up is competence. The skill, like people are really skilled in whatever job they’re doing. Like in engineering teams even are technically very talented. I mean, you can’t have a high performing team without core capabilities, whether it’s whichever role the team is playing.

But beyond that, you know, passion shows up, you will find that I don’t have to ask people to solve a problem if a problem needs to be solved and they know the solution they will solve it. They’re self-motivated, I’m not kind of going around ripping people saying, “Oh, what was not done today?” A standup or a weekly thing status is more of them just telling, Hey, what’s going on rather than being a documentary proof that I was actually productive this last week. So self-driven part comes in, A-players attract other A-players.  The team gels very well. When I talk to people in a high functioning team, they don’t talk about that.

I’ll say, “What are the issues we are having?” Very seldom do the talk about people being, you know, am fighting this person or that person doesn’t help me out. Blah, blah, blah. They don’t talk about people. They don’t talk about as, as problems or consent. They don’t even talk about processes. They talk about problems, customers’ problems. Every time I have an engineer or asking me, “What is the next big problem I can solve? Because I know you think I’m busy, but you know what? I think I can handle more. Just let me know what is the next big problem?” And I say, “This is a high functioning team,” his or her biggest concern that they want to ask.

Yeah, VP or whatever is I want to solve a big problem and let me, you know, ask what he, I want to raise or I want more titles or what have you. They just want to solve big problems because that’s what they say around them. And let me finish it by the biggest thing that kind of gets into just delivering results, which is obvious, but taking ownership to me, taking ownership is kind of the culmination of all of this.

People are not just solving problems. They are actually identifying problems. They are defining problems. I don’t give problems anymore to my team members, especially if they’re senior enough, I pointed them in a certain direction and they come to me with saying, Hey, she actually, you know what? There are 10 things that we need to do here.

Five of them will be directly customer impacting to get to those five. And one is maybe infrastructure or process or what have you. But we need to do these 10 things. Here’s kind of my ideas about this. Here are the things that I don’t have the expertise for. I need you to kind of find me the talent or the support for this.

They come to me with a plan. My job is, well, you kind of have a plan, let me see how I can put things around so that we prioritize this. And so the problem was identified by them. The solution was identified by them, the delivery of the results. They know what success looks like, and they are diving to get that done. It is amazing when that happens.

And that happens a lot, especially in Productiv now because they’re a small company, our interns take on and come back with problems and solutions to the extent of shipping things to the customer. And this is what I mean by running a marathon, right? When an entire team is the problem identifier and a problem solver, you naturally start thinking more.

The longer I can think about the longer run. Teams can think about the longer run. Sure. That’s what high performing teams look like, teams which take ownership or other teams in which every individual takes ownership of solving the customer problem and do. And that’s what a high performing team looks like.

Christian McCarrick: [00:16:25] Excellent. And now that we’ve painted that picture, which I agree with in a lot of ways, it, it just, there’s just something I’ve played sports teams and college and stuff growing up too. And there’s just something that gels, it’s something you can’t necessarily put your finger on, but you just know it. And you know, you’re part of it and it’s really amazing to be on.

And I feel that way too, when teams get that way. But for a lot of managers that might be listening right now, maybe their team hasn’t reached that level of maturity yet. What do you think? Because there might be getting frustrated, like everything else it’s we’re in this like instant gratification sort of environment today, but what do you think is a realistic estimate?

If someone inherits a team or they’re building a new team from scratch, like these high performing teams don’t just happen overnight, if you try to work on it, what do you think would be a good expectation from a timing standpoint, to really start seeing a team gel and come together and start performing, like you just mentioned.

Ashish Aggarwal: [00:17:14] Yeah, I’ll tell you, honestly, this is a tough question because the situations can be so different. I mean, I can not blurt out a numbers. There’s no formula for this, but I would say the answer is probably a few months. Now, if it takes close to a year, then we are doing it wrong. If it was done in three weeks, well then I don’t know if there was too much wrong to begin with.

Right. So if it’s a decently sized team and if it’s not jelling very well and not performing, there could be talent issues. Like there are talent gaps that we haven’t identified, we just don’t have big problems to solve their vision gaps. Right. There could be cultural gaps. The team is fighting against each other, other than the competition outside.

Right? I always tell my teams, the competition is outside this building competition is not called productivity is called something else. If you are competing with each other in a healthy fashion, that. Thank do we, you know, kind of in a funny way or in some other way, one of each of them that’s fine, but there is no competition amongst each other.

I’ve seen teams where the culture of collaboration is not there. Competition is there. Cut throat culture is there. And honestly it could be also, the managers have to look change starts from self first, right? Are they defining the vision? Are they letting these people–their team members–solve the problem?

If they don’t have large problems, are they asking their team members to say, “Find the three biggest problems” and are they trusting them? Everybody wants to work in a great team. Not for lack of intent or desire. No engineer comes and says today, “I will kind of add this note. Reasonably one comes and says today, I want to be inefficient.

And today I want to be in politics and whatnot”. They all want to make impact. I will say the honest path forward. Is really just to find what is broken by talking to the team, right? Whatever is missing. Yeah. I have asked sometimes my teams and they give me really good, bad directions to say, if we don’t have a good vision or we don’t have the right tools, or we are just missing this capability in the team, you keep asking us to do this.

We don’t know how to do this, or you don’t ask us enough. We have great ideas, but you just keep seeing your own ready ideas. I mean, of course we are limited. So in a typical team, I would say if you have to change people around, like if you have to get different mix of talent in, by hiring or by letting go, then it might take six months to kind of get to a high performing team.

If you already have the right talent, if you’re just fixing culture and processes, culture takes a little bit more time to fix. Honestly processes should not take that long to fix. So processes can be fixed fairly, fairly quickly. So I would say anywhere from one to six months, depending on how bad of a situation you are.

Christian McCarrick: [00:19:57] Sure. And to reiterate too, for the listeners, what you said too, is one of the paths to get there is asking your team, right? It’s not going to come from you. So like you mentioned. Make sure to wear your team, ask them, they’re on the ground. They’re the ones that might be blocked. They’re the ones that’s doing a lot of the work.

So you’d be surprised at how creative, as you mentioned, not only problems, but a lot of them probably have solutions. And if it’s a safe enough space, make sure you create that for them.

Ashish Aggarwal: [00:20:22] Absolutely. Absolutely. And let me add to that. Please ask them not just what is wrong with you guys. Please ask specifically, “What could I do better as a manager?” It seems to be is it’s okay for you to say, “Hey Ashish, you are doing XYZ wrong.”

Christian McCarrick: [00:20:40] Absolutely. I a hundred percent agree with that because part of the problem might be you, like you mentioned with one of your early mistakes, they might be afraid to say, you’re the one blocking everything.

I think we can move twice as fast. And maybe you don’t realize that because you have a blind spot. Right. So yeah, absolutely. Okay. Great. So one of the things too, and I think you’ve mentioned this in the past, but I see so many teams working on hard problems because a lot of times teams, like you mentioned, high-performing teams, they want to work on hard problems, but how do you help a team or how do you help the team decide what’s the right hard problems to work on? Like as a leader in an organization, how do you help provide guidance?

Ashish Aggarwal: [00:21:16] I’m going to challenge that a little bit. High-performing teams don’t work on the hardest problems. Right. High-performing team work on the most impactful problems and they understand the customer. The customer could be, there was a team which is working on solving the problems of fellow engineers or for the sales team or whoever inside of the company.

But that’s their customer. High-performing teams take ownership of the customer’s problem. And then they say, here’s the highest impact problem. And maybe for this solving this problem, the solution is pretty low tech. Maybe the solution doesn’t add too much to my resume, but the problem is not that I’m trying to estimate assuming the problem is I’m trying to have impact on my customer. And that’s where, when you say high performing high performing doesn’t mean that their performance was so well that their all resumes look awesome after, you know, whatever one year, but they have done some cutting edge technology and discover that a lot of them’s or whatnot.

No a high performance means that their customers say, “”Oh man, my problems are solved in record time. And in fact, these teams are solving more problems that I could have thought of myself, but you are the customers that representative in your team. So high-performance teams, when they start thinking in these terms and it comes from everybody, you are rewarded.

Yes, of course we appreciated that as a problem, which is very hard to solve. And so putting the right people around it and give you enough time to solve that. Sure, but we measure results by impact. We measure results by results in some sense, right? Not by the effort, correct. It’s irrelevant how busy I was, the only relevant piece is what impact did I produce or what I produce?

It’s not always, by the way, when I say impact, it’s not always dollars. It’s not always revenue. Depends upon the problem. It depends on thecustomer. Define what is going to help your customer and that’s what teams do now. And yes, high capability teams, what they do then is because they are free to define problems and think of the hard problems or think of highly impactful problems.

Yep. They know their own capability. Trust me. They trust in their own capability, much more than a manager does. And every single time my teams have outperformed what I thought they could do. Every single company, regardless of how much I believe in the team, they always surprise me. And so when I asked them to pick up the high-impact problem to solve, they were not shy of picking up a problem, which was very highly impactful, but I would have not did because it was very hard to solve. It was risky for me as a manager to come into that. You just need to agree that this is a high impact problem. And as long as we agree on that, don’t worry about it. We got this solving it. I understand it’s hard, but we got it.

We’ll do it. So then naturally then pick up the hard to solve problems as long as they are high impact. So yes, you do see hard problems getting solved, but it’s from the other perspective.

Got it.

Christian McCarrick: [00:24:17] No. Excellent. Yeah. And I appreciate that. That was good. And moving kind of to the marathon, not sprint topic. I mean, even mediocre teams are poorly run teams, rig you can potentially accomplish a lot of things in a short period of time, but there’s usually a lot of bad consequences that happen with that. Maybe burnout or lots of tech debt, but it takes a really good team to deliver consistently over longer periods while maintaining that team health and morale and everything else.

Right. So you’ve discussed this before solving short-term problems versus taking shortcuts. What are some of the examples you see of teams that take shortcuts versus long-term problems. What are some of those categories that you’ve run into?

Ashish Aggarwal: [00:24:53] So there is,there’s always a mix of tactical and strategic problems that you need to solve. And again, it comes down to what are you asking our teams to solve? Are you going to ask them. Every week, every month or whatever time frame about some tactical things that they have done. And because they’ve checked that box and the result is there to see, and they will naturally work towards solving the bugs or the asks from the, whatever the sales team, or if you give them space, if you say, “You know what, it’s okay to attack a very big high-impact problem and it’s okay to pick a problem.” They are not to deliver that impact of, they take you six months to actually write that up. All of that. It’s okay. I’ll wait for six months. I’ll give you the resources. I understand for six months. You will not ship a feature because you are building the infrastructure.

Christian McCarrick: [00:25:42] Sure.

Ashish Aggarwal: [00:25:43] And that’s what the marathon is. The results of that will only come maybe in six months, maybe in one year. In big companies, you can plan multiple years in advance in small companies. You don’t quite say, H””ey, this problem will be solved, which is the impact will be five years from now because you have plenty of problems, which are kind of low hanging fruit before that. The marathon really comes from sayin, “Hey, how are you just doing this thing to check a box?” Sometimes it’s time to fix up. Well, it was beating customers down. You need to stop the bleeding. So you put a band-aid and move on, but good engineers. Whenever we ask them, I went out, I asked them saying, “What is the right way to solve this? They will always come back and they’ll say, “Here’s a shortcut.

I can take that. You’ll be happy. You won’t know this.” The next engineer who comes in will say, “This is bandaid,” or three months later, “We’ll have to rewrite the whole thing,” but you know what? It’s going to be my fault then. People who take ownership. they say, hI’m not going to do the shortcut” unless there’s like super urgency.

I’m not going to take the shortcut because you are promising that the company is going to be around for the long time that my customer is going to be around for the long time. If I actually solve a good long-term problem for the customer, and I take the time to solve it because someone will be happy and I’ll be happy because my performance and rewards or whatever whatever’s in that culture is aligned with their not incentives that are aligned with solving problems, where we don’t need to resolve them.

Christian McCarrick: [00:27:00] But that incentive is not always the case. Right? So I think one of the examples, and I agree with you, but I think one of the examples is that lots of managers face I’ve faced is the trade-off discussions and dilemmas that you have, whether it’s a fundraising effort next rising a next raise of money or large strategic customer comes in and you’re getting some of the pressure maybe from above. And, you know, as you mentioned, being an engineers, this is the right way. But the right way might not be the way that gets us there in the time needed for something. How do you manage that? Is there a decision matrix you have? How do you handle those situations?

Ashish Aggarwal: [00:27:33] Yeah. Yeah. I hear what you’re saying. And I hear the, at least from my perspective, I hear the confusion. When I say, if you’re running a marathon, it doesn’t mean that, “Oh man, whatever I’m working on, don’t ask me for two years after…” When you run a marathon, you still run it mile by mile. There is a checkpoint by checkpoint, right?

Yeah. It’s just that you run it up passionate because you know that, you know, I have whatever 26 miles to go. You don’t just sprint to the first one and just blow yourself out and get to the a hundred meter line. And then you’re dead, right? When I asked my teams that we are running a marathon, I still say we need to deliver results one mile at a time.

We need to do things in a phased fashion. We just need to think maybe five miles, maybe all the way 26 miles ahead. That’s what running a marathon means. Right? You think of the long term, but you do execute in the short term. So the trade-offs we have to make short-term trade-offs we know that that this is a term trade off.

This is away suboptimal, what that we are doing for some special circumstance, right. That’s customer really wants it tomorrow. And they know that will kind of a half broken solution. And they will then be patient for us to build a proper solution in whatever three months then on whatever a fundraising thing or whatever, as long as the trade offs are deliberate, it’s okay, good. Yeah, absolutely. And when you start doing deliberate trade-offs, you’ll probably do the classic 20/80 thing. Right. You’ll make 20% tactical things. And 80% of marathon meetings and marathon meetings again don’t mean that they don’t mean slow. They just mean they will last for a long time.

Christian McCarrick: [00:29:15] Yeah. Got it. Excellent. Excellent. One thing. And we’ve touched about this before briefly. How do you go about ensuring that your teams maintain a deep technical excellence over time? How do you make sure that the bar is always high for bringing people onto a team and then that the team itself sort of maintains and then increases actually their technical excellence over time.

Ashish Aggarwal: [00:29:38] Yeah. You know, I might sound like a broken record here, but again, it goes from taking ownership, right? When my team members come to me and say, you know, we have identified this problem. I think I kind of know the solution. I don’t know how to implement it. I just don’t want that technology very well. If there is somebody else in the team who knows that, then I say, do you want to partner with them?

They will implement it, but you will learn it along the way. Because, you know, you are passionate about this thing. You want to be the owner of getting this thing to the finish line and they will say, “Yeah, absolutely.” Nobody says no to learning from others, especially if they propose the problem and the solution to begin with.

But the interesting thing that happens is a lot of times, especially in Productiv, I find people come to me with solutions. Yeah. They say, actually they come to me with problems. As they say, “we don’t know the solution. And actually we don’t know if anybody else in the company who knows how to solve this. What do we do Ashish?” I said, well, if we can wait to hire somebody, but we don’t even know to hire there, or why don’t you do the research? And then they find a technology or some solution, and then they say, “Well, it’s a new one.” And then they start saying these things now more and more, “Ashish, I need a couple of weeks to train myself on this thing. Then I need a couple of weeks to train somebody else on this thing.” And then they’ll do this thing because that’s the baby will go because they are just focused on that outcome. Right. They’re like I have identified a problem. In fact, I’m more deliberate. The only one in my way is myself. Let me say it another way.

The way you pose the problem is “It is my requirement that my team knows the latest technologies and are up to date on technologies.” And the way I am posing this back to you is it’s not my requirement. I’m not the only owner of this part. Why do we need people to be technically savvy and up to date with the latest technologies or keep learning?

Because it increases capacity increases our ability to solve bigger problems or solve problems faster. Well, whose problem is it? It’s not just mine. Yes. I happened to be the leader of the team, but it’s not just my problem. If it’s everybody’s problem. Then the solution is in front of everybody too, right?

Increasing their own technical capability to solve bigger and better problems is as much their problem as it’s mine. And so then once they take ownership of this part and my team members, I’m very lucky. They all do. So I have very, very funny opposite conversations with the team..,

It’s a technology

Christian McCarrick: [00:32:11] looking for a solution sometimes. Right? And it’s always challenging to do that.

Ashish Aggarwal: [00:32:16] What’s pressing them to some, I just need to sometimes bring them back saying, Hey, I know you’re passionate about it and you’re going to learn it. But you know what I mean? Can we put two people together and both of you learn kind of the similar technology, rather than both of you learning two different technologies for the solution.

I cannot mandate passion. I cannot mandate learning. Learning-passion for learning-of solving problems that come with that higher capacity that comes from inside from the team. I just need to hire the right people and I need to have the environment around them. Sure. That everybody’s in this culture.

Christian McCarrick: [00:32:52] Absolutely.

Ashish Aggarwal: [00:32:53] I tell you then things work on autopilot. I take no credit for this, by the way, things will come autopilot around in great teams and in performing teams.

I agree with that too, right.

Christian McCarrick: [00:33:03] Sort of build the environment, build them the space, give them the support they need. Give them the challenging environment and magic happens, right?

Not that sad, but yes. You know.

Ashish Aggarwal: [00:33:14] No, you said it right. Magic happens. You hire great people. You give them hard problems to solve. You actually let them solve the problems or maybe even better. You let them identify the hard problems to solve and magic happens.

Christian McCarrick: [00:33:28] So I’m going to flip this. I love that part of the conversation want to flip to this one next question, because you have direct experience with this. And I know I have a lot of listeners who work for some of the larger companies, Google, Facebook, et cetera. And they’re looking at maybe smaller companies, maybe a smaller startup, or maybe a mid startup. How would you advise managers coming from some of these larger companies today to be successful at a smaller company, maybe like a productive or something else where they’re coming from a Google or Microsoft, et cetera.

Ashish Aggarwal: [00:33:54] Sure. I love the companies. I’ve worked at a few of them.  But I would  say I loveProductive the most. And the reason, the way I tell people who are coming to small companies is you need to unlearn. I’m not pointing at any big company by the way, but you need to unlearn some of the things that in general, big companies kind of pitch you. This is the way to succeed. Right? Big companies sometimes teach you a waterfall model to succeed. Not my problem model.  X percent really define the vision. Y would you define the actual problems? Somebody else will actually make sure the customers use it. Somebody else will track it.

It works in a large team and a smart team. It’s funny. You actually get to solve every problem that you raise your hand. And in fact, it’s not just allowed, it’s actually expected that you really punch above your weight class. Lots of companies will, by definition will ask you to punch below your weight class because that’s safe.

We can throw money at the problem, right? If I need 50 engineers for something. I’m going to hire 70 because I can afford it. I, my main priority is to make sure that the project succeeds on time. Sure. You know, smaller company. If I need 10 engineers to solve something, I’ll probably hire three. Then I would say, go figure it out next, phase it out.

Let’s do what you can. But let me also remove the shackles, remove the politics and move the bureaucracy around. So when you’re moving to, from big to small company, be ready to take more ownership, ask others to take more ownership and expect that that essentially sometimes translation to be more hands-off right.

Understand the domain. You will not be spoonfed to a large extent, be ready to enjoy the shock of normal bureaucracy. When you think of something, you will be able to do it, you won’t have to kind of fill a form in triplicate and stay in your lane. Things like that are going to have to define your lane.

There will pronanly be no lanes. It sounds chaotic, but it’s that freedom is what gets the speed. If there’s an analogy I make me that helps me think a big company is a cruise ship. It moves as a lot. It takes a lot of time for the cruise ship to turn. If you will come in and want to turn a cruise ship, you will have to go through, you know, seven layers before you get to the captain and on the cruise ship and whatnot, which is fine because it’s a big cruise ship.

You can’t just really turn on a dime or do whatever you want, but it’s going in a certain direction. It has momentum and whatnot. Small companies are like a jet ski. Their super power is not their big size and momentum. Their super power is their speed and agility. Yup. Speed. As in how fast we can go in a certain direction. And as it is, if we can turn directions, both are very important.

So that’s the difference. If you are cruise ship, captain or manager, or what have you, once you jump to a jet ski or a speed boat, or what have you, that’s what you are jumping for. You’re optimizing for speed. You’re optimizing for making decisions without a lot of data you’re saying I can make mistakes and I can change my mind direction because we can do it very quickly.

So speed is what you optimize for. And is it, it is what helps you in kind of keep correcting your course and finally find your path. That’s what I would say. There are a lot more different things, but that is probably the biggest thing that I will say.

Christian McCarrick: [00:37:24] Okay, perfect. Awesome. And one of the, part of the show too, which I like to ask is. Any recommendations you have for a book, a podcast, a show, something that could be something you read 15 years ago that stayed with you or something you read last week that you find interesting.

Ashish Aggarwal: [00:37:39] Don’t have a podcast or even a book to recommend. And there are a lot of different things, but mostly the books that I read, advise me more about big companies, how to work in a very different thing.

Then I joined Amazon. Amazon has said “Here are our 14 leadership principles” and they are public. You can go read them on their website. And they don’t track them. But two of the most important ones I found were customer obsession and taking ownership there a lot more, all of them are paid by the way. Sure.

And honestly, personally, just for me, I thought I knew both of these. Hell I’ve been in the industry for, I don’t know, whatever, you know, 15 years or something like that before that I’m a director of coming from eBay. I was, you know, some senior person at Microsoft, blah, blah, blah. I know what thinking about customers means.

I know about what taking ownership means. Amazon just really taught me what these things actually mean. To the extent that after a couple of months, I was like, “Hell, I actually did not know these things.” Like you want to have a fit proposition. Wasn’t quite to my advisors. Go read those principles. See if you can find some things around whichever principle that strikes you as, Hey, you know, I want to learn more about that material on the internet to learn about that.

But dig a few principles and understand them deeply. And my two favorite ones are customer obsession and taking ownership, but understand them deeply. What do they mean? Customer obsession from the perspective of I’m not a company’s agent anymore. I am the customer’s agent taking ownership is not that I will complete my task, it’s about, I take ownership of that, of actually delivering the impact is or whoever the customer was. And even if I’m not doing all the work, but I will get it done and I will push for it. And I take ownership of the entire thing, including defining the problem if it needs to be.

Christian McCarrick: [00:39:28] Sure. Sure.

Ashish Aggarwal: [00:39:29] I have learned more from my peers, my seniors, my leaders in all of these companies and men in Microsoft and eBay and Amazon Postmates out in front of them finding those topics to go after.

So if there’s one thing you want to your listeners want to read, I would say go hit Amazon’s leadership principles.

Christian McCarrick: [00:39:48] Yeah. That’s why I love asking this. Cause there’s all different kinds of questions and it can go very meta. It can go tactical. So, yeah. And I’ll put the link to that in the show notes on simpleleadership.io as well.

So people can go kind of find that one last thing. What is the best way to people to contact you? Whether it’s about Productiv or just in general, they want to reach out to you. They have some questions or want to chat with you.

My email usually

Ashish Aggarwal: [00:40:10] is the best. Cto@productiv.com productive, just like the word productive with ‘E’ or without “E’, both should be able to work, but cto@productiv.com or LinkedIn. My name is Ashish Aggarwal.

Christian McCarrick: [00:40:22] Excellent. Excellent. Well, Ashish, we’re kind of coming to an end to this conversation. I’ve greatly enjoyed having this time to talk with you. I love talking with other engineering leaders. It always gives me some more motivation to kind of go back and be better for my teams and help to support them better. So I do thank you for your time this afternoon.

Ashish Aggarwal: [00:40:39] Thank you, Chris.

Christian McCarrick: [00:40:40] Thank you for listening to this episode of the Sempra leadership podcast, hosted by me, Christian McCarrick. If you’ve enjoyed the show, please subscribe and don’t forget to leave a review on iTunes, full show notes, and additional information can be found on simpleleadership.io.

If you know someone who would be a great guest for the show, or you want to share your own experiences, please drop me a line. We’ll see you back next week for more technology, leadership tips and advice. As I interview more top software engineering leaders. .

Christian McCarrick  

This is simple leadership. Welcome. Thank you to our sponsor, all zero for helping make the internet a safer place by offering identity as a service and supporting this podcast. We’re here to learn from New and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams. Do you want more engineering management leadership tactics and information? Subscribe at simple leadership.io to receive the latest updates from this podcast. Hi, I’m your host Christian mckarrick. This is the simple leadership podcast. Welcome back. Today’s guest is Susan bond. Susan is an executive coach who works with technology leaders. She’s the former CEO of Travis CI and has spent over a decade in technology mostly at scaling companies. She’s currently building a product to support new leaders and making the transition from management to executive leadership. She’s a regular contributor to Fast Company where she works for the work life section. Covering leadership, personal effectiveness and productivity. She has an educational background in psychology, organizational behavior and community organizing and received her coach certification from the coaches Training Institute. On today’s episode, we discuss the issue of loneliness as a new software engineering executive. Good afternoon, Susan. Welcome to the show.

 

Suzan Bond  

Hi, thanks so much.

 

Christian McCarrick  

Absolutely. Now, where are you calling in from today?

 

Suzan Bond  

Brooklyn, New York.

 

Christian McCarrick  

Brooklyn, New York. Awesome. You know, I actually get a decent number of my guests on the show from New York and I grew up there. I think a lot of my listeners know so always great to talk to somebody, a fellow New Yorker.

 

Suzan Bond  

Wait, where did you go up? I did not know that.

 

Christian McCarrick  

I actually grew up out on Long Island. And then I my parents and I moved to the Upper East Side. So I kind of kind of split between Long Island and the Upper East Side. I go back there visit my family. It’s great.

 

Suzan Bond  

Oh, very cool. Yeah, that’s awesome.

 

Christian McCarrick  

So you know one thing I always ask all of my guests to just a high level brief background, you know how you got to be where you are today. You know, what makes you who you are and what you’re doing today.

 

Suzan Bond  

I’ve always been really fascinated with the place where individuals and organizations or larger groups meet my whole life. I studied it, I read books about it, you know, I read books about leaders when I was 12, there was like this whole shelf in the library, and I read every single book on that shelf. That was like such a nerd. My Library card was my best friend. And so I’ve always been really fascinated with that. And that’s sort of an introduction to sort of, like, how I got into the field. You know, I studied psychology and organizational strategy and those things in school. And then I think that the path really into where I am today started with, I managed a project management department in technology. And so that was my first real introduction to management and leadership. And I thought, Oh, I like this. And that took me into going to get coach training and it kind of just went from there. So that was sort of like the genesis of of that and then I do stints as Director of Career Development, and then my most recent was CEO of scaling startup. And I’ve worked for myself off and on. But I’ve also worked at every stage of business but most frequently, scaling startups. That’s like sort of my… I like it. Like I call them the awkward gangly stage of like the juvenile, things are growing. And that’s the stage I like.

 

Christian McCarrick  

Yeah, yeah. I kind of like that, too. And I keep going back, you know, to the thing, and it’s very painful. But you keep going back. I don’t know why sometimes. That is right. Feel, at least I feel I can make one of the greatest impacts. And that always feels good, right to take it through that adolescent stage.

 

Unknown Speaker  

It does. There’s a lot of there’s a lot of like, risk and potential stress, but there’s also high reward and some people I think, if you enjoy the chaos there, and making sense out of it, and that’s what’s exciting for you. It’s a really great time of the phase of business to work and so we share that in common.

 

Christian McCarrick  

Yeah, total anecdote. I was at a dinner last night. With Plato, it’s an organization I actually do some coaching with. And one of my first mentees that I had years ago there, as a beginning manager, I just saw him on the platform as a director now who is mentoring other people. And I kind of thought that was so cool.

 

Suzan Bond  

That’s, that’s awesome. Yeah, that’s great.

 

Christian McCarrick  

So kind of as a coach now, especially with executives and managers, and I have often asked the question of engineering managers kind of what mistakes they made. But in your case, you know, I can ask you what mistakes other people made that you see in coaching them, you know, going from that transition from manager end or that transition from manager to lead more executive.

 

Suzan Bond  

Yeah, mistakes I made too.

 

Sometimes you’re like, “Oh, you spot that mistake? Yeah, you got that one? Yep. Did that one? Yeah.” I would say that. I think there’s a couple of big things. I think one is just understanding that making the leap from manager to leader it’s just really, it’s different. It’s much bigger than me, people think and people who have Then in executive leadership, say, I think then move from manager to leader or executive was a bigger jump then from individual contributor, so to speak to manager. And I think part of it is because we don’t treat leaders as if, like, we think, oh, the well, they’re big, they’re ready to go. They’ve got this. They don’t need support, like, that’s why we hired them. And I think that’s part of it. And I think where they struggle is a couple of areas. One, and before this, even as a manager, many of them derived their value in their work, what they thought their value was. So for many of them, they derived their value or what they thought their value to the organization was was in executing and getting things done even as a manager, right, you’re still close to the work, you’re managing the work, you’re making sure it’s getting done. And they have a hard time making a turn into being an executive. It’s really about overseeing and influencing. You know what it what that means, right? It’s like you have to make that turn. And I find that the ones who really struggle is they’re still going down and trying to get into the work and like, wait, but I need to get my hands on the code. You know, I think I need to get in there. And, you know, folks have said to me, I’m nervous, I don’t feel confident in my role anymore. And when I said, What’s that about? If the code something goes wrong in the code, I can’t get in there and fix it. That’s a great example of what you know that that shift the mistake, right is that they don’t realize that it’s like a mental shift.

 

Christian McCarrick  

Mm hmm. And a loss of control and power, I think in some cases, right? their comfort,

 

Suzan Bond  

right, and how they see themselves—”I get stuff done for the company, I can ship but now it’s like, oh, but now I have to influence Wait, what? What’s that right?” So they have to derive value and change their their mindset shift right along with a loss of control because you do have to work through other people.

 

Christian McCarrick  

Exactly. And Do you have any tips then for managers making that transition to executive, any like top thing you would say, hey, focus on this, or you need to learn this anything that stands out to you.

 

Suzan Bond  

Yeah, I mean, a couple of things. One is really understanding that you’re making a transition. I know that sounds basic, but sometimes people just think, Oh, yeah, I get more autonomy. I get to have more impact.

 

Unknown Speaker  

Yes. And you need maybe a pay raise, pay raise, right? Yeah.

 

Suzan Bond  

Yep. Autonomy impact pay, raise, and make sure that you don’t underestimate the mindset shifts. So making sure you get support, I think, inside your organization, developing also a network of other people who are executives, some who maybe are further down, but other some who are maybe closer to where you are. So you have people to talk with and help learn from other people’s mistakes and help you see yourself and then of course, get an executive coach because they can help you. I mean, it’s, you know, they’re paid. That’s what they’re paid to do.

 

Christian McCarrick  

And we’ll get into that a little bit more. Yeah. You know, I think the main topic today, you know, as we chatted before this episode to focus on is really around the loneliness experienced as an engineering leader. Now you have interviewed and coached many tech leaders about their struggles. How would you say the concept of the theme of loneliness for ranks as far as their kind of top struggles?

 

Suzan Bond  

I think it varies a little bit depending on time in role. I think that leaders who are more experienced would say it’s their second leadership role, or they’ve been in leadership about three or four years. I think by then they figured out their support systems and they’ve been able to process and say, Oh, it’s not just me who’s feeling this, there’s not something wrong with me. There’s, again, it’s like I’ve undergone this shift and that’s why but I would so I would say like as they get more experienced, loneliness gets better. Those I don’t know that it always goes away, depending also on who else is around them and what the organization is going through. But in terms of like new leaders, I would say it ranks in like probably like the top three. I would say that’s pretty high up.

 

Christian McCarrick  

Yeah, no, definitely. I mean, you are an executive yourself to, you know, how did you kind of struggle with some of that loneliness as well?

 

Suzan Bond  

I did. You know, more than I sort of thought, I think it surprised me a little bit. And honestly, it snuck up on me. I didn’t realize until I was like, I feel lonely. Why do I feel stressed? Why do I feel so tired? Yes, the calendar my calendar was busy. Like any executive, right? I would get up at five or six in the morning sometimes to work with my European folks. But then I would have my Pacific Coast both two or three o’clock then they want you know that I’m supporting them. So sure, there were long hours and a great number of demands. But what I discovered was I was losing energy from because I felt lonely and I didn’t have quite enough support systems. I think it was also you know, I mean, depending on the size of an engineering leader You will definitely feel that for me, it might have been a little bit exacerbated because my role as a CEO was really supporting the entire organization. Dear me like so I think that it was exacerbated a little bit by that.

 

Christian McCarrick  

Sure. I was reading and I think in the post that you wrote online, which is a really good post on this, and it will put it in the show notes, simple leadership.io, if any wants to look at that and read it in more detail. I think there was a quote, even on your Twitter stream you put on there about the concept, you can be in a crowded place, but still feel lonely, right? And it’s like you have meetings all day you’re not like with people. So being around people does not mean you can’t be lonely. Those are not the same thing.

 

Suzan Bond  

Exactly. I think it’s like what do we understand loneliness to be personally, I have never felt more lonely than when I was in a crowded room and I didn’t feel understood or you only mean like, I think it actually makes it feel worse. But the worst part is that we don’t get that we’re live but you’re around people all day. How can you be lonely?

 

Christian McCarrick  

Yeah, that’s right. You know, out of curiosity, and will continue Kind of on this film industry. But what were some of the other top struggles that you know execs go through as well, I’m just out of curiosity.

 

Suzan Bond  

I think part of the thing that executives can struggle with is the influence piece, which is, okay, so you’re used to working in your team. And now you have to work across an organization. Right? As you know, right. You have to work with product, you have to work with marketing, you have to work with the people team, you have to work with revenue or sales. And I think that can be really hard because they have to that means that they have to define their also they have to define their team differently. You don’t have any say over those people. So that means influence and how you work with them. And that collaboration becomes critical. And I think that that I think that that’s just that’s something that many nearly all of my execs we talk about every single one of them talks to me.

 

Christian McCarrick  

Yeah, and I think that that’s a good one. You know, I’m just kind of curious about some of the things you you’ve noticed and that aligns a little bit you know, I can talk about that all Day Two other struggles. But we’ll focus on this topic here today I could talk all day about all these great things. I think one thing you also mentioned that that caught my eye in your article was the concept of loneliness versus solitude kind of wanting to go into a little bit about what you’re talking about in that order.

 

Suzan Bond  

Yeah, I mean, I think loneliness is really about a state of mind. It’s not just about being alone. It’s like what we said, you can be in a crowded room and still feel like the loneliest person, like you’re on your own little island, which is awful. I’d rather be alone and feel lonely than being a big room and feel. But loneliness is really about a state of mind. And it’s like feeling misunderstood or not connected to other people. And I think, I mean, I think about a lot of it is like, such as existential angst, but it’s like a deep, feeling unseen, you know, or like other people just don’t connect with you, which is a very tough feeling. Whereas I would say solitude is a much more positive place where we’re going internal, this time. But instead of sort of in a negative way, it’s about understanding ourselves better and thinking about like, what do I think about understanding what’s on my mind? How do I really perceive that issue or feel about that issue? Or what are other ways I can see it. So it is more about going internal and a really positive way.

 

Christian McCarrick  

I think that time is super important. That self reflection time that solitude time where you need to whether you’re an introvert, you need to recharge, or you need to just do that strategy planning, you need to think about the future versus the fire that’s at the door, which is an executive. I think that’s another transition that I think people have to go through right thinking a little bit more about the future and not just the current fire because you have to, there’s delegations, all the things you need to do to try to deal with that, which you know, we’ve talked about in the past as well. But I want to go into the details of in your article and then the post you put out. I want to go into some of those details you mentioned about some of the top causes of information, kind of going to Some of those and one of them you mentioned was gaps and information that gaps information can exacerbate some of that feelings of loneliness. So let’s go into that a little bit more. What do you mean by that?

 

Suzan Bond  

You know, listen, there’s a big trend around transparency. And I love it. I am all for it. I think transparency is really hard to live. You know, I mean, like, it just is, I love the efforts, like if you think about buffer buffer is doing a tremendous amount of work around organizational transparency, not just internally, but also externally. I think that’s wonderful. I want that trend to continue. And I think people even if they’re not in, let’s say, a radically transparent organization or a stated value. I think leaders are still trying to be as transparent as they possibly can. It’s something I think that actually keeps leaders up at night. That’s what I hear from leaders. I know what kept me up. Am I being transparent enough? Am I being open enough? Am I giving enough context? And the struggle, you know, as I’m sure you know, is that there is just simply information that sometimes you can’t see for legal reasons, or for there’s a ton of people reasons doing like, over but like personnel, you’re like, I went back to the 80s there, but like things that address people’s, the humans in the business that you just can’t share. And I think that those gaps in information can be hard because then the team doesn’t actually have always have all of the, they don’t have all of the information and you’re sort of like, trust me.

 

Christian McCarrick  

Trust me,

 

Suzan Bond  

which is awkward as a leader, right, you’re like, I understand why this may not make sense or why it’s tough. And I think that the result of that gap in information is that the team members can be upset about things and and not because they don’t understand which I it makes perfect sense to me, right? Like you don’t understand the decision. I’m always like, why but why did you do that? So I think I can see me being upset about that. And I think what can happen is that then leaders feel misunderstood. Are the people think? I think sometimes what can happen is either they can look at you like you’re incompetent, or they can look at you like you don’t care. And then of course, that can probably feel lonely, when those are not your experiences. That makes sense.

 

Christian McCarrick  

Yeah, totally, you’re trying to do what’s best for them, and maybe the company, they don’t know that. And as a leader, you have to have somewhat of thick skin. Because you’ll get, you’ll get attacked, whether it’s in person or in a group setting or you know, on Slack, and you’re like, and you can’t, in some cases, defend yourself not because you can’t say something and then you do have to go that will trust me, they don’t have the context. And it’s rough. You know, I’ve read studies to that by withholding things, whether it’s in any type of relationship that increases your stress levels, and this is the same thing.

 

Suzan Bond  

I would love to read that article actually, I think that’s exactly it like with withholding things done definitely increases stress. For sure. Well And I think it’s really interesting to I made just made a connection to, you know, if we go back to what we were talking about earlier, which is what are some of the the areas where new execs can sort of fumble a little bit related to influence is building trust. And you because you have to have trust because of those gaps in information. It’s going if you have a little bit there, then that, trust me, goes a little bit further. You know what I mean? 

 

Christian McCarrick  

Bhe trust nank.

 

Suzan Bond  

Yeah, yeah, exactly. building that trust bank. And I think a lot of times execs come in and they want to prove themselves they want to have a big strategy document. And my opinion is spend time like doing someone’s called it like the interview tour. I cant rember they called it and I think that that that the listening to her, I think the listening to her is actually just as powerful around that building trust. So when you get to the gaps and information phase, you have some foundation for a relationship.

 

Christian McCarrick  

Yeah, no, I agree. And I’ve gone through this even even in my career. current role, as you mentioned, the personnel issue, someone might for whatever reason is needs to depart the company. And then the rest of the team feels like you aren’t transparent enough. But what are you going to do? I mean, you can, when you mentioned there’s legal reasons and two, it just might not have worked out, I might have a personal reason or a health reason or any other things that you just you can’t disclose.

 

Suzan Bond  

Kinda also protect that person, because they have a right to privacy around—maybe they’re dealing with something. It’s hard. And of course, at the same time, the team members probably feel shocked because for them, it might have came out of the blue even though you had been working on it most the time for a long time. It’s always that balance.

 

Christian McCarrick  

Yeah. And not to get into a flame or anything. But I also have noticed that the concert transparency, when you’re dealing with more of the millennial generation, I’ve also seen that there’s more expectation of this full transparency, which they will do to each other. But you know, it doesn’t necessarily, there’s some things as you mentioned, us can’t talk about or sometimes transparency. There’s just so much information that if I was to give everyone everything, they’d be overloaded and couldn’t do their jobs.

 

Suzan Bond  

It’s a fire hose, right? Well, and also for you to sort of digest it and to be able to add context in a way that they could understand takes a tremendous amount of effort and you have to like is, you know, you gotta juggle your priorities. Where do you put your energy? Which fire Are you trying to put out? Because you are surrounded by them?

 

Christian McCarrick  

Absolutely. Kind of getting to one of the other points to power dynamics, in your experience, and in talking with the people that you also coach, define how the power dynamics and kind of add to that loneliness factor.

 

Suzan Bond  

Yeah, so when I say power dynamics, I think this is actually a really hard one for most execs, because even though they have more autonomy, they don’t quite realize that other people see them show differently. Sure. Right. So when they might toss off a comment. People are like writing a lot. Oh, you said to read that book. I read it and it’s One exact told me that they were like, when did I say that? Well, you mentioned it in this email. And this was a real moment of where this, you know, it was about a, you know, very technical topic, and then the person thought they were going in that direction. And leader was like, Oh, no, I just, I just thought you might be interested in it. So they don’t think they realize how much a tossed off comment might impact. And you know, power dynamics are not just I mean, it’s about your actions, right? What are you what are your actions? What are you reinforcing it even as simple things as like, if you are co located where you sit, who go to lunch with, and but it’s also all of those communication and the way that we speak to them. And I know I talked about in my article, I worked very hard to connect with my team. And they were all in Europe, and I was in New York working remotely. And so I worked really hard to connect with them. And I realized, and I worked really hard to build trust with them really hard, and I realized I will always be their boss. And we were pretty darn close. closes a team. But I think that was a moment I thought, Oh, yeah, this is a very different relationship. I’ve been a manager many times, but I’m not used to being you work with the CEO you have influence across the company. Now I was like, Oh, yeah, I mean, there was no conflict there for us. But it was just a moment where I realized, Oh, I doesn’t matter what I do this power dynamic is always going to be

 

Christian McCarrick  

Yeah, absolutely. Even with my teams, I’ll have some icees. And they may be will feel reluctant about scheduling just a meeting with me or skip level or and it because oh, I’m the VP I’m so busy. I’m in charge of all the stuff I you know, I’m not as important like, and it hurts me a little bit, because that’s not how I try to come off. Right. But as you say, it’s that power dynamic, and it’s just assumed,

 

Suzan Bond  

Right, exactly. And I think that’s true what you said about thick skin and it does hurt you and and you have to learn how to not let it hurt you because you know, you’re like that’s not how I feel at all. Yeah, and I think in some ways you have to accept that no matter how hard, you work to reduce that power dynamic that is still there. And you have to keep finding ways I’m sure as you did to make sure they feel welcome or to reach out to people so that you can try to, like remove as much of that gap. You can erase it but as is to narrow it to as small of a crevice as you can make it.

 

Christian McCarrick  

Yeah, absolutely. Now, I’m going to ask you kind of a specific scenario, under the power dynamics issue. There’s always the case like if you’re an icy and you get promoted to a manager, and then you have to manage your former peers, that’s one level. But do you feel that going from you know, kind of a manager to an executive is even a stronger kind of pull there like it’s a stronger dynamic difference, maybe due to competition or more power dynamic seems that do you see that at all with some of the people you coach?

 

Suzan Bond  

I definitely think it can be that way. I think it depends upon what’s going on inside. Organization around openness and transparency, how execs are viewed. And I think also the previous relationships that you’ve had in in the organization. I mean, we all know that there are some managers who’ve been promoted, and people are really excited. And there are some who are promoted and people are less excited I because of lots of different reasons people people are humans. But I do think there is a bit of that leaders have to be cognizant of that that relationships will change and that there can be there’s just an adjustment period there.

 

Christian McCarrick  

You also mentioned the unrealistic expectation on leaders. And in one case, I think you mentioned in the article as well, someone mentioned to someone you had coach and sort of mentioned, how do you show kind of that vulnerability, which is important, but at the same time, like projecting confidence and steadfastness, especially in times of crisis, where your team is looking for you, and if you are panicking, they’re going to panic. How do you do that balance? How do you coach the executor It is to find that balance.

 

Suzan Bond  

When that person told me I just thought, wow, they really, they just articulated that so incredibly well, that challenge that they face. Because there is a call for us to be, I think at the same time, we expect leaders to be perfectly up, but actually also want them to be vulnerable. It’s like these two things happening at once, which is an interesting sort of place for the years to occupy. That one big variability is also the size of the company if you have like a bunch of VCs because there’s also more stakeholders that you actually have to be aware of customers and internal team and, and VCs and investors and all of that, those sort of things. I think that’s an interesting challenge. I think that first of all, you have to understand what’s right for you, as a human being some people tend to just be a little more guarded than others. I tend to be open but guarded, like I’m a little bit of a tweener in that way. And so, I think that you have to find the place where maybe you feel a little bit of an edge To be vulnerable, but not so much where you feel like so uncomfortable, like you might throw up joining me. There’s a little place that I think, how can I share the real things that are happening? And I think it can be simple things. Like, I know, this is disappointing, I’m disappointed to, or this didn’t work out the way I wanted to. And I’m looking at that. I think simple statements can even small things like that can help just give a tiny peek into a leaders mind.

 

Christian McCarrick  

Sure. I think that’s important showing your human I think goes a long way. You know, it might take some of that pressure off of being you know, superhuman when you’re not. You also mentioned helping with some setting expectations. You mentioned a morning ritual. Having a ritual in the morning can kind of help you prepare, what are some of the things you might recommend for a person looking to do that?

 

Suzan Bond  

Yeah, actually, I think I’m morning ritual. So glad you brought that up a morning ritual is really important, I think for every leader before their date. gets pulled into meetings and everything else so that they can listen to themselves. I think morning is great. But anytime that you can take that is fantastic. And I think really the goal of it is to just really have a time when you can block out all of the inputs, so that you can listen again listen to yourself. Part of that will be I think ideas come up about handles and how to handle situations. You’ll crystallize how you’re feeling about something, what you maybe need to say, or I know when I have a my mornings of solitude. I’ll often come up with like, Oh, wait, I perceive it this way, but they’re perceiving it that way. Oh, so I need to communicate differently. You know, I think there’s lots of ways you can do it. I personally think writing is one of the best ways you know, like literally hand writing. I know we’re all in technology, but handwriting there’s something they’ve even said there’s something different about the way your brain processes when you have when you hand write and when you have a writing instrument in your hand. And so I think that’s actually very important. And I think a lot of leaders don’t do that, because I think they’re so busy taking care of everyone else they forget.

 

Christian McCarrick  

Yeah. And you’re right. It doesn’t matter. I mean, I know some people who do something, they get up early, and they’ll do it in the morning. And others. It’s kind of the thing they do before they go to bed to help unload their racing mind, put it down, prepare for the next day.

 

Suzan Bond  

That’s another way to do it. As long as they get that done is wonderful. I know for me, it was the thing that really helped me a ton.

 

Christian McCarrick  

Yeah, great. Now, another topic that near and dear to my heart, poor support networks, which I think for me has been one of the biggest contributors to kind of that loneliness feeling and as I talked to kind of some other executives and other managers as well. I’ve mentioned this before, it’s one of the reasons why I started this podcast, just to be able to jam and chat and you know, have a little bit I call my our therapy session.

 

Suzan Bond  

Love it.

 

Christian McCarrick  

Other leaders What are some ways that leaders can help to build support networks? You know, what are some of the ways that you can help co or you help coach people to say, one? It’s true, you don’t have a good support network, especially a newer executive, how can you go about building one?

 

Suzan Bond  

If you don’t mind, I want to step back for a second. George, I think one of the unique challenges about being a leader is that why they’re actually more important, because everyone should have one. And I think it just gets harder as you go along. And the reason it gets harder is because of all of the pressure and all the things we’ve talked about. And I think also, there’s fewer of you. And you’re all going a million miles an hour, and you’re just like, there’s a fire, there’s a fire, there’s a fire. And so I think that what that means is it gets harder to do and also we’re not used to doing it because in some ways, our support network we have to work a little less hard earlier in our career because we have more natural peered forms of it. Right, exactly. We are peers or other people who understand when you get to be No leader, there’s fewer of you. And then also even reaching out because sometimes feels scary because of all of that confidential information that you sure right? You can’t talk to people. Yeah. Well, right, you’re like, so this thing sort of happened, you know, my friend, right? Like, it can be tricky to find that balance and it can lead you to self isolate, and not so I think part of I just wanted to go back to that, because I do think it’s a little bit different. I think it’s important for everyone. But this is the first time we’re not the first time but I think a very big shift when someone actually has to create one. So people don’t know how to do that. And some people don’t they get to that point in their career, and they don’t really know how to do it, like I always did my naturally I just reached out to people. And I think it’s more about like having a plan, recognizing, again, I’m big on transition, recognizing that you’ve made a transition you have pushed off onto a new land and you can’t see the old one. You’re on the middle of a big ocean, going to new land that you think is around the corner. So So a couple things. I mean, it really is about, I always recommend that if you’ve heard of the gallops done some research about employee engagement is to work for Gallup certified strengths coach, I’m a big fan of their stuff. And most people think that polls are how they make money, but they actually make 85% of their money through what they call human capital consulting. They’ve great stuff. But so they talk about employee engagement. And one of the important factors is having a best friend at work. Interesting. Yeah, that didn’t actually make the article because I mean, it was 2000. Yeah, I couldn’t include it. But having the best friend at work is much easier earlier in your career, and I think it but it’s still important for leaders. So finding a best friend at work, probably someone else on the exec team though it doesn’t necessarily have to be I think that that’s one thing is making sure that you have that confident that person who you can be like did you see that thing? How Mike What do you think about that you right, where you can just they have a lot of context and they have the similar information. So you can can just be, you can let down and be yourself and not have to self monitor. I think that’s actually the one of the things that is super important to it can happen, but just to make sure that you have at least one of those folks inside the company. And then of course, networks outside are also really important, right other exactly where you feel even where you can just talk about the broad strokes, even though you won’t be able to talk about the specifics those that can make you feel less lonely, like, Oh, it’s not just my company, or me. I mean, that’s part of why I write what I write is because I want to make I ultimately want leaders to feel less lonely and to feel like “Oh, got it, oh, there’s other people experiencing the same thing”, even when I’m not writing about loneliness is actually a massive reason. I write what I write. And then I’m going to say, obviously, hello, executive coaching is very good for that. And increasingly, companies are really investing in that. But I would say the other thing is Is I really am not trying to be self promotional, I just…

 

Christian McCarrick  

No, no.

 

Suzan Bond  

…really believe in it. And then I would say the last thing is making sure that you actually have outside interest. Like, remember that you have a life outside of the company, even if let’s say you’re not talking directly about work, that’s maybe a good thing. Having social time you’re being a human being reminding yourself that you’re not just always being watched, and you feel a lot of pressure, but that you’re just

 

Christian McCarrick  

laughing and being a human refilling your kind of coffers and getting some self worth to outside of your, because you might have a terrible week or something in your job. And if that’s the only thing you have, that you’re valuing yourself on, well, that’s pretty bad. But if you can distribute that out to whatever else you do, you go to the gym, you walk you yoga, you do art, and you can kind of get some of that good feeling and confidence from other things than the low one one. It will be an averaging effect and not a total effect.

 

Suzan Bond  

It’s a really good point because you can get so consumed. Yes,

 

Christian McCarrick  

I know, to my detriment. And one thing I want to point out too and again, Back to your coaching piece is most execs are probably going to report to the CEO or maybe a CEO, coo. And they just are not going to have the time for you. Right? So if you think you’re going to be exact, and you’re going to be coached by your CEO, I mean, you might learn by osmosis. But I mean, from experience to, you know, you’re very rarely going to get that wisdom an hour long one on ones where there’s this like coaching thing going on, they might point out things you’re doing wrong or becomes a very tactical, or you might get a good job. Back to your point. I think that’s why it becomes even more important for execs to have that coach because it’s a little bit of taking a place of the CEO and, and Frank if you’re in golf, or basketball or wherever you have a coach. You know why sometimes management is different, right? It’s a skill, you can learn it, you can hone it, you can get better, why wouldn’t you want to have every opportunity have to advance yourself and improve?

 

Suzan Bond  

Yeah, I do think that folks, we don’t realize that How little of that time that will get much development or, you know, support unless it gets really critical with the CEO because they are just so busy. I mean, it is no shade on the CEO so you know, busy and the loneliest person in the company for the most part. But yeah, you have to take control of your getting that support you need in a way that I think it ramps it up even though you maybe have done it early in your career. You’re right. It’s harder. You have to you have to work harder at it.

 

Christian McCarrick  

Yeah, absolutely. One even a specific theme on this kind of support network to I want to I want to talk about your second that I’ve personally found is the specific challenges of being a technical executive, where I found most CEOs and other members of the exec team are usually not technical, right? They don’t always understand the technical needs. So you’re kind of on an island in the executive team. Yes. Where they just Why do you have so many people like I don’t understand Like, why is a third of the budget going to engineering which they don’t understand about? So it’s

 

Suzan Bond  

why can’t we all be co located? Why do we have anyone remote?

 

Christian McCarrick  

Is this something that other kind of executives have mentioned to you as well?

 

Suzan Bond  

Yeah, I think it’s a really good point. Because, depending on like the structure, sometimes they’ll be you know, you know, exec teams, their structure really depends. Sometimes there’s the CTO, and VP who sit on the exec team, sometimes the CTO, sometimes it’s dual VPS. But it can be very lonely. The only kind of group that might sort of relate might be your product, folks, depending on how your product VP or you know, CPOE, depending on how technical they are. Yes, I do think that they do feel lonely. And I think part of that goes back to the making that turn around, oh, I’ve got to really figure out how do I connect with folks from very different functions? How do I make sure that the people team or operations or sales understands the question strengths. I have why we do need so many people why we can’t just add a feature overnight why these infrastructure costs have to be so high. All of those things I work almost not exclusively with technologies. But most of my folks are from the software side like technical CTOs VPN. That’s the people I work with the most. I think it’s absolutely true, that they I think, in some ways can feel extremely lonely because of that. Yeah.

 

Christian McCarrick  

And it’s a skill. I think you need to get a CS degree part of that curriculum is not how do you work with your CFO? Right? How do you create budgets? How do you justify expense? How do you translate tech product speak into Excel spreadsheets and PowerPoints and things that the rest of the executive team might understand. So I think that’s a skill that it’s training some you get it over time, but I think it’s something seriously lacking as you come to the executive About how to properly manage up and out at the exact level

 

Suzan Bond  

100%. Because when you’ve been going up in the throughout the engineering part of the organization, many times you will talk to other people outside of your area, but you’re not having to influence or collaborate or you don’t need as much. And now this is really different. It’s a different kind of skill set and try to I also like, oh, how do I talk about the importance of this? Make sure they understand why it’s important. And how do I put it in words? Because I’m used to just saying to another engineer, well, you gotta get it edited up, right.

 

Christian McCarrick  

Yeah, totally. Something a whole nother podcast, we could talk about, you know, you’ve also written about the lack thereof of executive onboarding. And companies like that is something I think, which again, it’s a whole nother episode, but just, I think for the listeners out here, too. I like how you put it in that it’s a transition, whether you’re going to a new company, or whether you’re at an existing Company transitioning into that executive role. I view it as a transition take it seriously and know that it’s not just the same old.

 

Suzan Bond  

Well, yeah, that, you know, I noticed that as a COO, you know, part of my job was really supporting the executive, the executive team. And I saw that right away that when, when execs might be, you know, coming on board and having a hard time with it, but I also did, just for some context, I interviewed a bunch of leaders last spring and last summer can just understand what their challenges were and, you know, hone in on that. I came up with three things and one of them was validated what I thought which was onboarding, it’s non existent. Like when I asked the question, people literally chuckled like, Did you mean I got my computer? And I got an invite for the executive meeting.

 

Christian McCarrick  

Yeah, pretty much

 

Suzan Bond  

but all of them really wanted that and we don’t do a good job at that again, because we have our perception around leaders being invincible and ready to go and of course, then we don’t want to be like, Hey, I’m I just got this role, but I don’t, I could use a little bit of help. So it was one of the biggest trends that I saw. Loneliness was the second trend. And the third trend was executives, you know, really need support around organizational, just some of the functional strategic like acting from an organizational perspective, they wanted more support around the organizational dynamics and working through that. So this person contacts that that’s where that comes from. And I the onboarding is the thing that really grabbed my attention and great, I think can help a lot.

 

Christian McCarrick  

I do recommend a book, their first 90 days, it’s not perfect, but as you’re going through a transition at any point, first 90 days is certainly a book there. I think there’s another book did you mention transitions, I think is another one.

 

Suzan Bond  

So good by William bridges is so old, but it’s so good.

 

Christian McCarrick  

Yeah. Any other recommendations you have books, podcasts, like anything else that you might recommend for my listeners,

 

Suzan Bond  

Yeah, a book that I buy for pretty much every one of my leaders comes into coaching is called multipliers. The subtitle is, you know it that’s I do. Yeah, the subtitle is how the best leaders make everyone smarter. It’s by Liz Wiseman. It’s a fantastic book that I think can help folks, especially around making the turn with basically micromanaging right like that, that going down and the influence. It’s just such a great book that I give all of

 

Christian McCarrick  

all of my books. I was discussing this with somebody last night, that book multipliers and they mentioned the kind of the converse of that, which is like the subtractors. Right, there’s the there’s the opposite of that and you have to kind of watch out for that as well. Now, you are a coach Now give me like the kind of the, you know, the two minute elevator pitch, you know, kind of what you specialize in and you know how you could help some of some of my listeners.

 

Suzan Bond  

Yeah, so my specialty is I tend to coach newer execs, who are making that transition Because I want to offer them support during that time, although I coach more experienced execs too, but I would say most of my folks are somewhere between one and five years and their first or second role. I’ve got one who’s been in a couple roles, but now the organization is scaling and they came to me because now they’re managing people who they’ve never done that role. And they had they were like, Oh, wait, I have that’s that thing we’ve been talking about, like, what’s my value in working through asleep, like confidence stuff like the confidence and making that turn them I work with them on on loneliness, influence around the organization. And then sometimes it’s around managing managers, which you know, is different than managing icees that is a different sort of thing. So it’s all around those kinds of things amongst others,

 

Christian McCarrick  

Okay. And what would be the best way to contact you if people want to reach out to you to, you know, inquire about your services, or just kind of some Thing triggered something from the conversation and they want to follow up with you.

 

Suzan Bond  

I’m a Twitter lover who’ve been on the platform for 11 years. And so it’s always a great way you know that folks can reach me at it’s at Susan bond as she’s ENVO nd I’m on the platform a lot. And I, my DMS are open. And I’ve been very lucky that I can keep them open but I answer questions folks write me all the time and I’m happy to answer questions there. You can also contact me on my website, there’s a contact form on there. And then my email is Susan at Susan bond calm. I love talking about this stuff. So I love it when people reach out because I enjoy it so much. And I love talking with other people who are thinking about the topic so

 

Christian McCarrick  

excellent. And as usual, the book recommendations and everything will be on my show notes on this episode. Simple leadership.io. Susan, appreciate the time. I had a great conversation today. Thank you very much for joining the show

 

Suzan Bond  

It was great, it is the most fun I’ve had all day.

 

Christian McCarrick  

Thank you for listening to this episode of the simpler leadership podcast hosted by me Christian mckarrick. If you’ve enjoyed the show, please subscribe and don’t forget to leave a review on iTunes. Full show notes and additional information can be found on simple leadership.io. If you know someone who would be a great guest for the show, or you want to share your own experiences, please drop me a line. We’ll see you back next week for more technology leadership tips and advice as I interview more top software engineering leaders

 

Christian McCarrick  

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We’re here to learn from New and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams. Do you want more engineering management leadership tactics and information? Subscribe at SimpleLeadership.io to receive the latest updates from this podcast. 

 

Hi, I’m your host Christian mckarrick. This is the Simple Leadership podcast. Welcome back. Today’s guest is Loïc Houssier. Loïc started his career as a security researcher in France and has a background in mathematics and cryptography. His career evolved to more management roles in software engineering, focusing on critical infrastructure of European administration’s working for Orange, Thales, and Naval group. He eventually decided to join a startup, OpenTrust, to help with growth and organize the teams and eventually became the CTO there. Luke joined DocuSign via the acquisition of OpenTrust four years ago and is today a VP based in San Francisco leading DocuSign’s efforts on mobile, eCommerce, and billing systems. On today’s show, we discuss mergers and acquisitions along with engineering team efficiency. Good afternoon, Loïc. Welcome to the show.

 

Loïc Houssier  

Well, welcome for having me. 

 

Christian McCarrick  

Absolutely. And look, I had the pleasure of having dinner with you a few months ago at a Plato event. I greatly enjoyed our conversation at that time. So I’m super excited to kind of continue the conversation and to have you on the podcast today. So thank you very much for joining.

 

Loïc Houssier  

Of course. And I’ve listened to your podcast more than a couple of times and I feel I was a failure or not to be a part of the people that you haven’t interviewed so far. So thank you for having me again. 

 

Christian McCarrick  

Oh, absolutely. Thank you. My pleasure. Also, Loïc, where are you calling in from today?

 

Loïc Houssier  

From San Francisco, so from the DocuSign office downtown San Francisco. 

 

Christian McCarrick  

Excellent, excellent, very close to me. I’m actually working from my home today in the East Bay, we’re pretty close to each other at least in the same time zone and in the same city. One thing I do want to point out to my listeners, I also apologize, I haven’t recorded an episode in almost six months. As some of you other engineering managers and leaders know, I’ve been running engineering for a super fast growing unicorn. And that’s pretty challenging. And it’s taking up most of my time. The good news is that I’ve been able to get some help on this podcast and will be returning to a more consistent schedule in the coming months. So definitely appreciate everyone’s patience  and thank you for all the listeners out there who have been pretty dedicated to the show, and have been inquiring when the new episode is coming out. And I can say, you know, when this launches, that’ll be a good New Year’s resolution to keep the show going. Like I asked all my guests, if you could just kind of give me a little bit of a brief background, kind of what you did to get to where you are today. You know what might be interesting to my listeners?

 

Loïc Houssier  

Yeah, so I’m now in San Francisco. I basically started my career in France, studied math, most of my time and ended up doing cryptography as my specialization of math. I started my career as a research engineer in the security field. I did that for something like three years and a half. In a big telco company, Orange, for people who are mostly in Europe. It’s a pretty big company, hundred thousand people, and that company is a pretty big structure. I’ve been working there for like three, three years and a half, I was saying, I moved in another big company like 60,000 employee called Thales, which was and still is working in the defense industry. And I was basically working on the security of critical infrastructure and mostly focusing on government’s *inaudible*. And I was there some kind of a half a security expert as you can be after 4 years of experience, but they call it expert anyway. But I was also basically managing the development of a platform that We were basically providing to, to our customers a woman’s. After that I had a nice opportunity to basically go outside of the software industry. So after seven, seven years in my career, basically inside a Thales group, there was a subsidiary called another group. And their focus is basically building submarines and frigate for the French marine. And basically, I took this opportunity to be outside of the software industry just to understand how the heavy industry is working. So I was there to help from an organization perspective with some kind of a program management background. And I was basically trying to apply what I’ve learned in that area, which was basically just amazing for my the rest of my career. So it was only two years outside of the software industry. That gave me the opportunity to basically help people that were way more senior than me, were more knowledgeable but as you could have field because I was basically newborn on this area and not knowing anything about what is a torpedo, well, what is a radar, but I still had to basically influence the way they work by providing some processes or tools, basically around their work. And that was one of the best experiences I had, which I could reuse as my job as a manager. So basically how to influence people where you don’t have the technical legitimacy anymore, which the more you, you climb the ladder, the less you can be really technical. So that was just an amazing experience. But it was still a big company. So after these two years outside of the software industry, I wanted to come back to my first love which was security and an engineering. So I had an opportunity in the tiny company of 60 people and they were looking for basically kind of a program manager with a security hat and working for the government. so I had kind of the perfect profile for them. And then they were 60. So I was so happy to have an opportunity to understand what is a startup. How this is working because I was mostly working on big companies with a highly processed and a lot of people supporting you. And I just discovered a world where you have to do everything by yourself, which has some downside. But the good side is, if you are able to do some impact there, the impact at this scale is huge for the company. So in that startup, starting to be like, some kind of a big Program Manager, and you know, having a dedicated software team because for my biggest basic customer, I needed to basically make some dedicated release with some specific modification for governments. And it was working pretty fine. And at some point, they moved in on the engineering side totally without any more customer relationship, and just helping teams to be more efficient. And I basically ended up being the CTO of that small company. And we move from 60 to 120 through an acquisition, and which was interesting because we called it a merge and not an acquisition. So it was basically two companies. As you can number one and number two in France in our area, and so ended up being 120. And that company has been acquired by DocuSign, four years ago. So managing, again, a merge of this time, it was a real acquisition. So we have been acquired. And I had to basically manage that. And I basically ended up going in San Francisco two years ago, who basically took on a bigger a bigger scope. And now I manage mobile, the eCommerce side to sort of self service side of the design. And I have some team in Brazil too. So this is what I’m doing right now. 

 

Christian McCarrick  

Okay, excellent. I love hearing how people kind of got to the positions they are today because they they really are varied. And it really shows there isn’t necessarily one path, which I think sometimes people think that there’s only one path to become, you know, software leader and the more people I talked to, the more I realized, and I hope my my guests realize that there is no true path. You know, I’ve often found in talking with some of my other guests on the show too that they’ve found that whether it’s in software companies themselves doing roles that are not necessarily technical, and or going outside of software engineering, I think it is those types of opportunities and experiences. I think everyone is pretty much said really helps them when it when they do become a software or an engineering manager. And those skills, like you mentioned before, helping you along the way on that path of becoming a better leader and a better manager.

 

Loïc Houssier  

Oh, yeah. When I started, so I was a security researcher. And basically, I was, so I was coming from a, it was an average University in France and the lab I was working at it was people from a school called Polytechnique in France, which is kind of the MIT in the US to give you a sense. So it’s as if I was coming from community college, or let’s say, definitely Bootcamp, and I was mostly working with people from the MIT. So that was just amazing for me, like the opportunity to basically ramp up and have all those brains that were basically running so fast compared to me when I just joined. And after three years I was, let’s say on par, I just I had this feeling so basically my ego was just too big. So basically when I moved to Thatles, in my first management role, my technical legitimacy was probably the first asset I was using to influence people. And then when I moved out of the software industry, I didn’t have that technical legitimacy anymore. So I had to put my my ego in my pocket and try to find other ways to have people listen to me. And that was honestly the best experience I ever had. So it’s just the understanding that you don’t have to be the best technical person in the room in order to make a decision or two, to make sure that people follow the same path and and listen to you was, was just amazing for me. That was eye opening. And I’m not sure that if I, let’s say let’s assume that I would have just continued the same road on the software industry. I may have become a jerk, honestly. I could’ve become someone with a big ego and just trying to be there. Just like “I know, I know I’m the best. I know what I’m talking about. So guys, you just have to follow me”, I could have become that person, honestly. But that experience, the fact that you’re talking to people that are just in a totally different field, you have to find the ways you have basically have to learn to listen. Because if you want to help them solving problems, you have to listen and understand what they do, and not assume from the beginning. So yes, that was that one of the suggestions I can give to people is try something that’s totally different. The experience that you will get there will be tremendous.

 

Christian McCarrick  

Sure. And I think the higher you go in software engineering, leadership and management, the more that you actually have to rely on those skills, not just downwards to your team. But as you’re talking with the executive team, you’re talking with people in other departments sales and marketing and you have to talk to board members. You have to rely on those non-technical skills to be able to translate as you mentioned, to have the influence, to have the proper communication, to get what you need to get done in a way that’s not relying just on your technical chops. 

 

Loïc Houssier  

Definitely, definitely. So as part of those two years, so one was working on submarine…the other year, I was working on nuclear plants. And I was kind of a deputy director of the operation. So I basically was a kind of a young guy. So walking aside, the really senior person on that area that was basically managing contracts with the French. I was a four wheel supply main contractor. And I was basically working with him and he was explaining to me how to manage the different contract, how to do claims on some contracts in order to achieve some goals strategically on other areas, because of the levels we can have between the different contractors. So trying to also understand all the businesses side and not only the technical side, trying to understand how they think and how they look at the problem was just tremendous. And now when I’m basically managing Europe and trying to understand what is important for my boss or  marketing or product commerce side, and it’s really helping me a lot to figure out and try to understand how they think. And not only being good at managing technical people on all my directors, so it’s definitely a big asset.

 

Christian McCarrick  

And something I asked all my guests is any mistakes you’ve made that you can publicly talk about, maybe protect the innocent or whatnot. I know. We all have probably a whole litany of them. But part of I think what so my listeners get out of this show is understanding that none of us are really perfect. And we’ve all had our mistakes along the way. Any ones that come to mind for you that you can share?

 

Loïc Houssier  

Yeah, basically, I will talk about two. So the first one was on my very first experience, so I had the team that I was assigned to for a government project. And basically I was stupidly assuming other people that will efficient well look at me, so I was like “They should be outspoken. They should speak loud, they should be always jumping on to new opportunities, they should provide value pretty fast in mostly working on a quick and dirty and not slowly losing time” and stuff like that. And I had that guy on my team. He was so slow. He was really slow. I just requested a small document for the particular customer to explain how we do things from basically organization perspective. And he was a guy that was on the team for quite a long time. And I said, “Yeah, I need that document pretty fast and it’s fine. basically give me a two pager and this is just what we need”. And after a week, he came back to me and said, “Yeah, just a couple of more days”, so “Okay, that’s fine”. And then like midweek after that come back to “Are you OK, are you good with the document? Can you provide it to me?” “No, no, a couple of tweaking again”. So basically, it took like something like three or four weeks to provide me with the document and I was totally going crazy because if I were me, I would have done like two pages in one day, it would have been good enough. So I went to my boss and I said, “Damn, I cannot work with that guy, that guy in my team. It’s not possible, took a month to provide that document”. And he basically clapped, looking at me and saying, “Congratulation”. So what’s up? “Why are you saying congratulations?”. He said “No, you just made your first management mistake”. I was kind of curious about it and pretty defensive. And he said, “So describe to me the guy”. I said, “Well, he’s too much on the detail and is always taking the time to be sure that what is written is right, and is not able to do some shortcut”. Okay? So basically, you know, the guy you know that this is the way you behave in What did you ask him by to provide me with a two pager like a quick and dirty. So basically, your mistake is that you assigned a guy to the wrong task. This is your fault. And that was the very first time that I basically looked at it in a different way and the way my manager was direct with me, so there’s a lot of learnings from that. So basically, my manager was a great mentor, and was fairly direct with me. So he was not trying to say, you know, everyone is different. He was really blunt and told me you made a mistake, and this is the mistake. I’ll try to think about the say it in a different way right now. So that was first thing that I learned from that is being direct is probably the best way to help people to improve. And as a manager basically is like it’s my role not to change people, but to understand how people are efficient in their own way and basically give them the work where they will be successful. So which is basically the way we did it after that the guy was working and we just curious about what it would be. I was happy to work on and willing, it would be feeling efficient and happy to work and basically manage all the configuration management of the project, which in the defense industry is something that is pretty huge. And you know he did amazing work, amazing work. I was really quick on judging that person just because he was different than me. And basically I learned that I was the guy basically world In that story, so I was lucky that I had a good manager calling me wrong on this. And that was early in my career. That was one of the best things that I’ve said the best mistake that I’ve done in my career. 

 

And I have a second one. So this one was pretty early in my career. This is usually what I tell to my folks is like, you don’t have to make all the mistakes early in your career, you have to learn from them, whether you are in your 20s or you’re in your 40s. And so I can talk about this one. So it was like kind of eye opening for me. Discussion again, with my manager, I read a lot about management and how you can manage your priorities and how to set them up and the difference between urgent and important. I used to talk about this, that that story and the way to look at management as someone that is juggling with eight balls, and you’ll see he has 8 balls and is not able to basically manage more than eight balls. Balls being project being initiative, this is only what he can do. And if a ninth one, he’s coming on to another one, he’s coming on top of it, he needs to drop one, I would say the least important of that and delegate that one to the people that are below. And each one in the basic organization. Is able to manage, let’s say, between six and eight balls. So basically, if everyone is dropping the least important balls that they are managing, at the end of the day that people that are like really working, they will stop doing the things that are less important for the company. I love this idea of way to manage the real priorities because there’s kind of a funnel where you know that the things that are the least important won’t be worked on. But I will say there’s a difference between understanding the concept and being able to apply that in day to day life. And coming back to my background, so I was kind of a program manager. So I used to do a lot of dashboards with a lot of KPIs and for quite a long time and I was always trying for each of my teams to understand all those KPIs. So I wanted to know anything, everything. So whether it is the throughput of the projects, the number of … and what are the SLAs on top of it. I wanted to have all those information. Even if I knew my priorities, and what will my priorities, I had the feeling that and this fear of missing out something. So I wanted to receive all those KPIs. And I was basically putting a framework for the semi boss team in order to for him to have those the information that I thought were crucial to drive your business or your teams. And you look at me say how much time do you spend on this? Yeah, I don’t know. But it’s, it’s obviously building the framework is pretty long and everything. He said, this is not where you need to spend your time. What are your priorities? So this my priority and say, “Okay, so how much time you spend on that?” “See, I don’t know maybe like, in my day, in my week, maybe a 15 to 20%”. He said, “Forget about those KPIs and spend 60% on those priorities, this is what I need”. And basically, that’s all it comes down to the what is your limit in terms of workforce, what you’re able to achieve, and it was always hard for me to let go and not see them, obviously, every single detail, but there’s so much only so much you can do. There’s only so much that you can look at. And I was basically at the time where I need to let go, I need to let go. And just basically, you know, so I won’t look at those KPIs. Just my guys will look at it. I need those teams to look at that and I just need to trust them. And they will inform me if there’s an issue on that so that I can just look at the right KPIs that make sense for me, and they were the ones that are really important. And so even if I’m in my 40s, and I’m a VP now, I was still struggling with that. And it was like two weeks ago, and that discussion was eye opening for me. So just you know, for the people that are listening to that maybe the takeaway is like, you don’t have to make all the mistakes early in your career. Even if you are pretty advanced in your career, it’s totally fine, to accept that you’re making some mistakes, and you can change the way you look at things. Two big mistakes, I would say that I can disclose. 

 

Christian McCarrick  

Absolutely. And I think it’s true. I think we do make mistakes every day. And as you point out, the the most important thing is being open to learning from them. Some of those learnings can come from not only your manager, but they can also come from your peers. And they can also come from some of the people you manage as well. So be open for learning all up and down and sideways as well. You know, you’ve mentioned a couple things, you’ve been a part of a couple of mergers and potential acquisition. And I think this is something that almost all managers will have to deal with at some point in their careers, right, especially fast growing companies. You know, it could be called a reorganization. And that really could be something that is pushed down to you or to something that is initiated by you yourself as a manager. It could be large, it could be small. There’s other types where you talked about two and you’re actually combining two different entities and what we’ll chat about that in a second, but let’s walk through some of these kind of scenarios. As a manager of teams, if you’re looking at your teams and you’re looking at again, as a efficiency are the things, what are some of the reasons that would kind of make you as a manager, look to want to potentially want to merge teams?

 

Loïc Houssier  

That’s a good question. I would say merge that I took my experience from was basically a business merge. So we decided to merge two different companies in which you basically don’t have the choice. And you just have to make sure that the merge is working well, and you’re trying to mix the culture, where that is basically a working product company. And then from that perspective, maybe a couple of thoughts, one mistake again, that has been done at the time. We called it a merge, but it was an acquisition. And when you have basically two different cultures, two different set of stacks and you have two teams that you need to work together as a one team, but they work totally differently. You need to be clear in the early beginning, basically what would be the set of cultural practices that will keep. In terms of merger was basically to say, in fact, it’s not a mergers it’s an acquisition. And I’m sorry, guys, maybe you’re not really happy with that. But you will have to convert within this set of practices or this set of stacks or the set of to set because for efficiency reason, we cannot have like, I don’t know, two CICD  processes, or so many stacks. So you will have to change. And this is one thing that we didn’t do very well in the beginning, is clearly set the expectations. So people were like, yeah, it’s a merge, but we want to keep our stacks. It’s another team. We don’t have projects together. So nothing was really clear. And that was probably one of the key learning that I have right now. It’s if and when we do acquisition, it’s to be clear on setting the expectation.

 

Christian McCarrick  

sure, from the very beginning, making it clear if there’s going to be a technology change or an acquisition, like you said, being clear about which one is going to be, I don’t say winning out right, but which one is going to be the ultimate path you’re going to kind of merge towards right or transition to

 

Loïc Houssier  

Yeah, and exactly what you said, you said, choosing the one that is winning out. But this is the feeling of the people that are already working, when you have to change your… your stacks to the the one that the other team is using, you feel like you’ve lost something. So there’s a feeling that you have to manage. But if you don’t do it, so if you don’t set the expectation in the beginning, people will always have this kind of fear. What I mean is, there’s a need for clarity, if you don’t have the clarity, people will always assume or they go on the path that is not the one you want to have. So it’s better to set the path in the beginning, even if there are some consequences to that. Some people may decide to quit because they don’t like the new set of stacks of your new set of practices or the culture. But if it’s clear in beginning, at least you can manage the consequences. If it’s not clear, it will lead to friction between the teams and a lack of efficiency.

 

Christian McCarrick  

Okay, and do you any tips that you would recommend for any, any managers that are leading teams right now that might be, you know, they’re getting acquired their recently acquired or you know, it might be something in the future? What are some of the top things you’ve learned? Maybe not as a, as a leader at an executive level, but more if you’re, you know, a line manager, maybe managing one team or senior manager. Any recommendations you have for how they can help their teams get through a transition like that?

 

Loïc Houssier  

Yeah, I guess the worst is the the uncertainty. Trying to be as transparent, seeking information. At first, I would say that the early beginning on the why. Why are we being acquired? What are the reasonings? Let’s say you’re part of the company being acquired, you need to understand why that your company is acquired. Is it acquired because they are looking for the tech stack or the piece of software that is fairly well complementing the offering. Are they mosty interested in it as a marketing asset, or is it they don’t really look down at looking at the stacks or the product you’ve built, but they look at the team itself. As a manager, you need to understand the reason for the acquisition to basically tell your team because uncertainty is the worst. And as the acquisition is moving, so during the due diligence, so after the deal is closed, basically explaining and trying to understand what would be the impact for the team and be clear. And in the beginning not trying to protect the team was as long as you can to protect the the identity or whatever trying to understand what is the overall goal of the acquisition. And if there’s a chance, let’s say I don’t know you’re part of an acquisition and they want to change the way you hosted. So you were in a Ws and they want you to move to GCP. Or you were using some monitoring system and they totally want you to change that how you will make it even the stacks. They want to change the language of your of your software and wants you to rewrite about of it, I think this is the kind of information that needs to be clear from the outset as soon as the as possible, because no matter what you will have to manage the transition will say sooner or later. And the sooner you know, the better you will be prepared and the better you and the people you manage, will be able to provide you the feedback. Some people will say, “You know what, if you’re changing that, I will quit”. So then you know, so you will be able to be prepared for that and to to manage that. If you don’t also seek those information and share that with your team. Basically, that would be way harder to manage. 

 

Christian McCarrick  

Okay, sure. Anything post acquisition—so you’re a manager the first 90 day. Is there anything important that they should look to do or try to manage through that transition? Because I know as you said, there’s going to be some uncertainty. It’s a little bit of unease, anything that a manager post the acquisition/closing should focus on?

 

Loïc Houssier  

Try to follow the change and not be reluctant to the change but with an acquisition you will go through change no matter what. Whatever it is, maybe you were using title when you will be using JIRA. Maybe it’s a downgrade, that’s fine. Maybe you were using, I don’t know get lab that you need to get her or maybe you were using Slack, you need to, to use Microsoft Teams or whatever. I would say even though it’s usually the the silly stuff. So for someone moving from the one that I would say instant messaging to one another, in the big scheme, it’s kind of silly, not really important. But this is the kind of stuff that basically will annoy most your team. So you need to be aware of the change and have the change to move as fast as you can. That is really important. The second aspect is making sure that your team has a mission, it needs to be clear from the beginning. Let’s say in the first 90 days, there will be a lot of work for the integration. Integrating the systems, integrating the product, maybe you’re doing some change in the stacks. But in the long run, what will be the mission of your team? And that is really important especially if the acquisition of the merge make you some kind of a satellite site. So I will give you an Example: DocuSign has two main offices, one in Seattle and one in San Francisco. But we have offices in Paris, in Tel Aviv, in Warrenville, in Chicago, and South Paulo. When 70% of your workforce is in basically the two main city sites in the US, you have to make sure that these, let’s call them satellites have a real mission. Because if they don’t have a real mission, it would be really hard for them to exist. So it’s, if you’re part of those small teams that have been acquired by your big thing, you need to be really clear and understand what is the mission so that you people understand that they belong to something that is bigger. And it’s, and it’s really important.

 

Christian McCarrick  

Absolutely. And that certainly helps with motivation as well. And I think one last thing to add on this is, as I’ve gone through some of these myself, there’s an urge, either by yourself or by some of your teams to maybe make a rash decision. You know, something that they might make emotionally, when, as you said, it might be something silly like, like an instant messaging tool, and they might be willing to change jobs over that. Well, I think in some cases, too, it’s give it a little time wait and see how things are so you’re better able to make a more sort of impartial decision instead of just a pure emotional one.

 

Loïc Houssier  

Yeah, I would also add, it’s important to understand because I’ve heard that so many times “Ahh they want us to change to their tool, but it’s not the best one”. And trying to first understand as a manager of that, the best solution for your team is maybe not the best solution for the company. That is something that is hard. So for example, I don’t know—the database. Maybe your solution is way better and more efficient for your product. But at scale, adding your centralized DBA team that are really specialized and able to choose one stack or one version of the database is probably better for the company, in terms of SLA in terms of performances. So maybe for you it’s not optimal, but it would be for the overall company. And that is one of the hardest thing to do is accept for the good of the company, that the your team is downgrading some of the aspects that they were doing. So that is one of the hardest thing to do. Because you have to be convinced yourself, which is hard. But you have to convince your team then this is not easy. 

 

Christian McCarrick  

Absolutely. I think that segues to into kind of the second part of this the conversation of what I want to get into around, especially as growing teams and companies grow that concept of what’s the most optimized thing for a team might not be the most optimized thing for the organization. And especially as you’re trying to build a engineering team that is operating as efficiently as it can and especially at scale. At some point, adding people linearly just doesn’t work. it incurs an increasing management cost. And of course, payroll is one of the largest expenses at a company. So what are the things that you have learned about scaling engineering teams and scaling them you know, as efficiently as possible throughout your career?

 

Loïc Houssier  

It’s a matter of prioritization. So when you want to grow and grow fast, my learning is focusing on hiring the right people is the number one priority. So you want your job to do, you want your job to do you have your, basically your release to, to go through the door, but if you want to, to scale, you have to hire other people that can make you scale. So when when we hire we try to surprise over here, we always try to find the people that have the network so that they can bring more people so that you reduce basically the kind of the lead time between the job offering and the people that come in. That’s one thing, talking about the tech stack. That’s one thing too, the more you bring out a new stack, the more maintenance it will need. So trying to reduce or converge into a standard in a company. It’s always good. And it’s kind of interesting and it comes down to the the way I do personally trying to manage things. There’s, we try to I don’t know if you read that book “The Zone to Win” by Geoffrey Moore. So it’s a different world basically world the famous one than “Cross the Chasm”, which is about product lifecycle and how to to reach your market. But he wrote the second one that he basically, I think he wrote it when he was working with Microsoft and Salesforce, basically (now I’m not trying to spoil it for people that want to read the book). He basically explained that there’s a way to look at innovation, try to be simplifying, there’s one side that is disruptive innovation, disruptive from your customer perspective, and something that is more like sustaining innovation or continuous innovation. So you have your current product offering and you add features on top of it. But those will say continuous innovation happens on the product or service that is already working, which is basically the bread and butter of your business. Here you cannot be too disruptive. So you cannot probably bring on new stacks or a new way to host, or a new way to deploy. You need work through incremental, small increment to make sure that you’re not disruptive. Because this is your business. So you cannot disrupt it. But on the other side on the positive, but you want to bring up a new service to the market on top of the portfolio you have, you can, you don’t have much customer yet. So you can be really agile there. And you can basically test new ways to host new ways to, to deploy. And so for example, talking about infrastructure, whether you want to be like your bare metal, have to do your managed communities on Google or Amazon. There’s a wide range of solutions. At DocuSign, for everything that is the core business, there’s one way basically to deploy the product which is on prem on our own data center as a new fairly, let’s say not cutting edge way. Because what we want to achieve is basically five nines and this is what we will achieve in terms of SLA, because our customers do not want us to basically mess with the, the desolace because of contract and when you sign a contract is is highly time sensitive. On the other side of the spectrum, we are providing innovation to our customer on some stuff that are kind of before and after the medical doctors signing a contract, preparing the contract or acting on the after the signature. And this is more using cutting edge technology. So we can have some stuff that are maybe, let’s say, are not yet mature terms of operations, or in terms of even on wage or, and but that’s okay, that’s okay, because we want to get fast. And we optimize for velocity, or compared to optimizing for stability, just trying to be on the growth side of things. So it’s, there’s two ways to look at the growth. So there’s a slow growth production business because you cannot just be like disruptive and the disruptive growth where we trying to adapt and to add more solutions to your current portfolio.

 

Christian McCarrick  

Yeah, absolutely. You know, I was just going to mention to even at Auth0, we have our core login flow is something that is absolutely mission critical and you know, that has to be met with the highest level of SLAs. But innovating around things like the dashboard or reporting or other types of things that providing gives us a little more flexibility to be able to innovate on that. Because even if that’s down for five or 10 minutes, it doesn’t have a huge impact. Now, we don’t want that anyway for lots of other reasons for perception of whatnot. But it, like you said, it does allow you to, to kind of innovate on the different areas of your product, depending upon how poor they are or not.

 

Loïc Houssier  

Yeah, maybe three, nine, it’s perfectly fine for this dashboard, compared to your very own audition mechanism where it should be at four or five nines because it’s so much critical. So yeah. 

 

Christian McCarrick  

Absolutely. One thing I want to talk about too, because this sometimes becomes a controversial topic is measurement and metrics. As an engineering manager, I have sometimes found teams skeptical and sometimes hostile to any type of sort of measurement and you know, talk about before wanting to measure everything with with some of your background, how do you recommend a manager to have conversations with teams about introducing metrics? And how they can be important and helpful.

 

Loïc Houssier  

I went a long way, as I basically talked before, I’m a data person and I love dashboards with like hundreds of KPIs that I can try to see and detect patterns to better understand how basically my teams are going. But eventually, now I can say it, I think it was, if not a waste of time, it was probably a waste of focus. So now, I would argue that, and this is what we are trying to do with my team is to focus the team on one or two KPI that makes sense. And so we did I did my offsites kickoff for FY 21 with my teams. And we spend basically that it’s all basically based on the company priorities and everything trying to define what is the definition of success for us. And our definition of success is probably not the velocity of the scrum teams. It’s probably not this level of details. We basically said okay, we need to release this by that time, and we need to change that architectural design. In a couple of, let’s say, two main milestone, basically team, so that this was the definition of their success. And we will all align that we need to optimize for that. And I’ve been clear that, of course, you want to be reactive on p ones on. But I would say being clear on what is the, the one big thing or the two big things that matters helps with the prioritization. Because when you’re trying to look at too many pieces of data or too many metrics. And again, and talking about the velocity of the scrum teams, based on the story point and everything Sure, obviously, on the paper is really good. It’s nice to see over time that your VC is trending down because the new employee are no more efficient and everything. So sorry, not the velocity 20 down, the trending up would be better. You get what I mean, right? It’s satisfying. It’s satisfying. At the end of the day, the energy you spend trying to put in business metrics. I’m not sure what types of business. I’m now in a position and I can say it. That is for me and my team that it’s probably better to focus on the one or two KPI that matters the most for the business, and making sure that those are good. And basically, the success will be there. And that’s all part of the discussion I had with my boss when I was trying to put that framework to have all this visibility and everything told me what about those small projects, if you when we say those big two, and all of those are basically are not very successful with dealing with that be a good year for you. So yeah, that would be a great year. If I fail to see I’m successful on those ones. So focus on those ones. I don’t care about the others. I will say it’s not I don’t care obviously about it. It was a word who said focus on those ones. So going down to the metrics now I’m trying to be as scientific as I can with my my lead. So that we are all aligned on what is the most important and the rest difficult without teams. They will have their own metrics. Maybe they will be a bit more detailed than I am. But at the end of the day, I’m fine. And I trust them perfectly to manage their… Yeah, I’m more like that now, it was a late change. So if I had to restart my mercury again, I think I will have less scrutiny on all those KPIs. And maybe be less picky when also working with my teams. 

 

Christian McCarrick  

Sure. No, excellent focus on what matters. And by doing that, you know, and if you measure what matters, then that’s the thing that the team again in a circle the teams will focus on. And then you’ll hopefully try to improve and make sure that they align to the business because ultimately, that’s the most important thing.

 

Loïc Houssier  

Yeah, and it’s, it’s funny, you mentioned “Measure what Matters”, which is a great book, and talking about rkR and stuff, and even if you look at those books, they provide a way to be aligned, but they don’t provide the granularity. And this is probably where I struggle. I won’t say struggle. I’m pretty okay with my career, but this is probably where I struggle with all those frameworks. It’s hard to adapt them or implement them in your ecosystem within your company and trying to find the right granularity. What shouldn’t be, what should it be those results that you put on the objectives, how many should be what what is exactly what you need? And it can depend, I think there’s no one size fits all. But, I more and more like, you need one objective and maybe one or two week period, that should be enough for your team, they should understand what is the definition of success with that little information.

 

Christian McCarrick  

Perfect. And as we kind of wrap up this episode a little bit. We’ve mentioned a couple of books here already. But are there any other resources that you have that you might recommend for a book, podcast, blog you like to read or anything that that either has helped you in the past that you recommend or something that you might have might have read recently?

 

Loïc Houssier  

Yeah. I would start with the one that I just finished basically, on Wednesday, when I was in Seattle, another snow which is the “Bad Blood” sort of story of theranos. And it is up at times. So I think this is that was a good book. Because for one time we were talking about a failure. And not about…on that will be more so maybe you are one of my two cents. But it’s when we listen to people that are like outspoken and successful in their career. It’s very impressive and I was looking up to those person that were like, you know, Steve Jobs but not only older, those guy like Elon Musk and everything and we focus on those successful people. You look at the gap between them and you and say “Damn, I won’t be able to, to achieve anything like that in the end”. That can be depressing, honestly. And again, you’re trying to understand what makes them successful, but you have this survival bias. So you’re looking at the other people that succeed, but what about the others—why people are failing? and I find that this book is for once looking at someone that was  brilliant, so being able to start that business at 22. And so she was basically uniformly recognized as a brilliant person. But still the company failed. And it was basically because of the poor management. There was some technical issues. But the poor management was one of the reasons. I found this book really interesting because for once we were looking at what management can play in your business. Even if you have a lot of money, you have raised a lot of money, basically end up losing your business because of your poor management. So that one was really interesting. And another one that I will mention is “Creativity, Inc.” I don’t know if you read this one, written by Ed Catmull. He was the CEO of Pixar. And he went also through an acquisition by Disney. And the book is about how to foster creativity in your teams. And there’s a lot of learnings for obviously engineering leaders because it tells how those guys were open to any comment on the other movies they were building. So from anyone in a company, everyone was able to raise their hand and say, “I don’t know, this piece this moment. I don’t like it because it’s whatever”. And they’re forced to have this energy where everyone felt totally allowed to, to express their concern about the piece of a movie.

 

Christian McCarrick  

Their legendary screenings that they used to do inside, right? 

 

Loïc Houssier  

Yeah, yeah. And that was just amazing. Of course, it’s obviously for people making movies, but you can definitely adapt for your own teams and try to foster that. I will say that kind of true, because it’s really easy for and I look at my key ones in my teams and they feel p ones being. Sorry, my young engineers so that I people that just joined a company straight out of college. In the beginning they can be shy and how can you during design reviews or during meetings—how can you give them the feeling that they are totally entitled to, to say what they don’t understand, or they want to challenge an architecture? So it gives you a lot of, obviously tips and stuff that you can apply. So I really love that. 

 

Christian McCarrick  

Excellent. Excellent. Well, couple of definitely good book recommendations that I haven’t read the theranos one, too, I actually have it, it’s on my book list to read. I do want to read that because I’ve got that recommendation from a couple of people now. What would be the best way for people to contact you? Whether it’s Twitter or LinkedIn or anything if someone had a question or or wanted to reach out to you about something on the show? What would be the best way?

 

Loïc Houssier  

Well, definitely LinkedIn. I guess it’s the easiest. I have a Twitter handle, but I’m probably mostly tweeting.  I’m not really I was really good at that. But definitely LinkedIn. So I think I’m Louic. L-O-I-C. There’s not a lot in in the day. So at DocuSign especially. So definitely the easiest way. 

 

Christian McCarrick  

Sure. And for those listening to the episode, I always post my show notes on simpleleadership.io so any links to the books we mentioned and contact information for Loic, I will certainly post on there too if you weren’t able to write it down during the show. So had a great conversation today. Always great to talk with you. I really appreciate your time. And so thank you very much.

 

Loïc Houssier  

Thank you for having me, Christian.

 

Christian McCarrick  

Absolutely. Have a good weekend. 

 

Thank you for listening to this episode of the Simple Leadership podcast hosted by me, Christian McCarrick. If you’ve enjoyed the show, please subscribe and don’t forget to leave a review in iTunes. Full show notes and additional information can be found on simpleleadership.io. If you knew someone who would be a great guest for the show, or you want to share your own experiences, please drop me a line. We’ll see you back next week for more technology leadership tips and advice as I interview more top software engineering leaders

 

Christian McCarrick    

This is simple leadership. Welcome.

 

Christian McCarrick  

Thank you to our sponsor policy room for helping make the internet a safer place by offering identity as a service and supporting this partner. We’re here to learn from New and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams. Do you want more engineering management leadership tactics and information? Subscribe at simple leadership.io to receive the latest updates from this podcast. Hi, I’m your host Christian McCarrick. This is the simple leadership podcast. Welcome back. Today’s guests are Tess hatch and Jasmine tested investor at Bessemer Venture Partners primarily focused on frontier tech, specifically commercial space drones and autonomous vehicles. She currently serves as a board member on numerous companies. Previously, she was a Mission Manager at SpaceX where she worked with the government on integrating its payloads with a falcon nine rocket She also worked at the of a startup using 3d printing and CNC machining to democratize access to manufacturing tests earned a bachelor’s degree in aerospace engineering from the University of Michigan and a master’s degree in aeronautics and astronautics engineering from Stanford. She was passionate about space exploration and imagines a future where we will all travel the space, she hopes to make the trip or self soon, just make is a software engineering leader with over a decade of experience. She’s worked in larger organizations like Amazon and the Naval Research Laboratory, but most of her career has been in the wild world of startups. She’s currently Director of Engineering and zero, and was previously VP of product at call nine. On today’s show, we discuss a range of topics, including what investors wish managers knew more about, and being good ally, and sponsor. Good morning Tess. Good morning, Jess, how are you doing today? 

 

Jess Mink  

Great. Thanks. 

 

Tess Hatch  

Wonderful. 

 

Christian McCarrick  

Excellent. And, you know, I love being able to podcast on location. And today we are recording from the Bessemer Venture Partners office here in San Francisco. So it’s always awesome. And not only are we on location, but we’re with two awesome guests today. So thank you for joining. Thanks for having us. Absolutely. So Tess, let me start with you, as I do with all of my guests, just to give them a little bit of color about who I’m talking with today. Give me a little bit of your story.

 

Tess Hatch  

So my story actually starts way back in middle school. When Sally Ride, the first American female astronaut came and spoke and being so mesmerised and excited by her journey to space on the International Space Station, and wanting to be an astronaut ever since. So from that moment, I studied aerospace engineering undergrad, I got my masters in aeronautics and astronautics engineering. I had various experiences and internships at NASA’s Jet Propulsion Laboratory where I saw the landing of curiosity on Mars. So awesome, those seven minutes of terror where it had either landed successfully or not, but it took seven minutes for the signal to come back to Earth. The time delay you could hear the mission controls heartbeats and breathing. Well, they weren’t they were holding their breath. And when that first image of the rover’s reflection on the Martian surface, came back to Pasadena, JPL, I have never felt so much adrenaline. Then I spent some time as a Mission Manager at SpaceX integrating satellites with the Falcon nine rocket. And I’m super passionate and love everything about space and rockets and satellites. And I imagine a future where one travels to space with the frequency that we currently travel on an aircraft. And I will be that first person on either a commercial tourist or as a as an astronaut. However, now I’m a venture capitalist. So I usually get asked, how did you go from aerospace engineering to VC, and I focusing in and work on our deep tech roadmap here at Bessemer, which includes commercial space, drones, autonomous vehicles, all those fun science, science fictioneque industries. So my answer is, I’m still very much an aerospace engineer and spend my time researching and learning more about space and drones and autonomous things. But as an investor in the broader ecosystem, rather than an engineer at one of the companies

 

Christian McCarrick  

Sure, you get an interesting view at that point, because instead of being focused on one, you really get to see the breath of what’s happening in the field, the forefront. Which is an interesting point, even though you’re a VC, but part of being a VC is is not only investing, but really empowering and encouraging the industry, that you have such a passion for it.

 

Tess Hatch  

Absolutely, I think the most important part of my job is knowing the history of the industry. So what catalysts or momentum drivers have really fueled and got the industry to where it is today. All of the players currently working in the industry today. And then being able based off of the historical and current market, what’s next and make predictions about the next catalyst driver to therefore place investments in those companies. So I love the “What’s next”? And where do I think the future of space is going, and then making investments in those companies and working with those teams on space to point out.

 

Christian McCarrick  

Excellent, excellent. Thank you, Tess. Now moving over to Jess, just give me a little bit to our guests about, you know, caveat, a Jess also works at all zero and super happy. She’s part of our leadership team. And also you’re on the on the engineering side. So this is such an awesome sort of conversation to have. Jess—a little bit of your background.

 

Jess Mink  

Sure. So I ran into engineering. Initially, by accident, I was at a science and tech focused High School and I found it fascinating. I love taking the logical approach to real problems in the world, being able to solve them in a way that where they stay solved. I’ve kept that thread of wanting to make change in the world and using tech as a tool to make that change. And as I’ve gone through my career, I’ve realized the biggest leverage is actually working with the people who are building the tech instead of the tech itself. Because if you change the way that people approach problems, and the systems that they’re building, when they think about those problems, that has such an impact, the ripples go out so wide. So that’s what keeps me really engaged and passionate about Engineering Leadership, is the way we can solve problems for people, right? Less like what particular new tech things are coming out.

 

Christian McCarrick  

With that, how did you get into so you got into technology as accidental, which is one of the reasons as we were talking about before this, that, you know, I love asking people about how they got into where they are today, you know, Jess is a senior director, so a senior leader at Auth0, which is, you know, I have to be somewhat biased. You know an awesome, fast growing tech company today. And I do this too, because not everyone in tech, and especially not everyone tech leadership comes from the traditional background, right? And I do this because a lot of my listeners here are thinking, who do I have what it takes to become an engineering leader? Do I have what it takes to start my own company? Right? And, yes, I mean, you do, right? If you believe in yourself, and certainly there’s some things that let’s get the experience, but you don’t have to have the pedigree in order to be successful, right, some of the most successful people out there have not had that. So it’s important to show that to all my listeners, if that’s what you want to do, and your goals to be start your own company, get investment or become engineering leader, VP of engineering or whatnot, at some point the future, go ahead and do it. Right. For those of you who want to become a VP engineering, sometimes I say, I’m sorry, right? It’s kind of a tough thing. Sometimes I want to be going to a back to an icy, but it certainly is challenging role. And I’m so glad that I’m able to do that here at zero. Now Tess, you mentioned you’re talking about frontier tech to right now, define a little bit of that you talked about autonomous vehicles and whatnot, is that is that kind of frontier tech means like, what’s next? You mentioned version 2.0, is that what that means?

 

Tess Hatch  

Absolutely, I love to actually go back to something you said regarding anyone can be a manager, anyone can create a company and in regards to anyone can create a company. Absolutely. Anyone can find a problem that’s large enough that multiple other people are also facing and come up with the solution. Now from there, the superpower really comes down to hiring the people around you that can supplement and cultivate and grow your idea into a company and therefore fill in either weaknesses of yours or areas where you want to remove various hats and give to other people. So I totally resonate and agree with with that statement.

 

Christian McCarrick  

Yeah. And so let me let me riff on that for a second. So for my listeners out there, and a lot of people are in Engineering Leadership today or an engineer managers, but they do have a dream of starting a company. You mentioned one actionable point, which is I think it was don’t do it alone. Right?

 

Tess Hatch  

Team. It is all about the team. Absolutely.

 

Christian McCarrick  

And if you’re a tech person, right, what would that team look like? Like when you mentioned complimentary? Like, what do you see, as an investor, what are the things you look for, as that makes up that great team, or the points of that?

 

Tess Hatch  

The ideal co founding team is a technical person and a business person, when it just comes down to too. As the team grows really dependent on the industry. So frontier tech is going to be a very different composition than SAS or cloud or consumer enterprise. But ultimately, it comes down to deep expertise, and an understanding of that customer, that market you’re going after, who really understand the problem, really understand the people that are going to be paying for that solution, and then have the ability and skill set to come up with the best solution.

 

Jess Mink  

You don’t need to come from a traditional engineering background to be amazingly effective. I’ve worked with a lot of people who have theater degrees and have come through boot camps. And I’ve seen those engineers bring the skills from those backgrounds to the team and make the whole team much stronger and more productive than if everyone had gone to the same university and brought the same way of approaching problems.

 

Tess Hatch  

I agree when it comes to certain industries, focusing on frontier tech, so space or drones, or I do look for that PhD in autonomous systems or PhD in computer vision into a deep learning algorithm that can do simultaneous location and mapping and yada yada, yada, some acronyms in there.So diverse perspectives being brought in different backgrounds is fascinating to approach the problem. Early on, though, I really do look for very deep, specifically engineering understanding of the problem.

 

Jess Mink  

 That makes sense, I was thinking more of a lot of the SAS type companies I’ve worked for where the deep technical knowledge is there. And it’s about scaling the team and about building the organization to the next level, which often involves a lot of communication skills and emotional intelligence that was lacking in the early team.

 

Tess Hatch  

It’s so important to start from the beginning with culture and cultivating your culture. From those first two people, because every single edition. There’s sometimes a difference between what you want your culture to be and what your culture actually is. And starting with, I always encourage and push companies to define what that is have an offsite or a day where they write down various morals that they agree on, or things that they want their their company to emulate and continually check back in if they’re following that roadmap. 

 

Christian McCarrick  

So that leads to something that becomes very, very important. So early stage company, and the team, most people pull together tends to be their tribe read their circle. And when you talk about culture is so important to set it early. A lot of times that becomes a bit of a homogenous culture, how, as a engineering leader, Jess, and test as a sort of a venture capitalist? How do you guide or coach those early stage companies at what point to start thinking that, you know, what you’re thinking here is going to be a little bit more narrow, because you don’t have kind of a diverse experience or thought, what you want to do to maybe broaden the appeal not only the company, but also set an appropriate culture?

 

Jess Mink  

I push really hard to make sure, especially when you’re setting up your initial leadership structure, right, not necessarily the initial group of cofounders. But the next layer of leadership after that, to be very intentional there. And to think about going outside your inner circle, at least two friends of friends are thinking about who in your circle maybe comes from a different perspective. Because once you have your senior leadership slots filled up, it’s really hard to go back and make sure that that really important team has a wide range of perspectives. 

 

Tess Hatch  

Absolutely. Starting your company, the easiest thing is to call up all your friends from school or your circle that I probably pretty similar to you. So you need to make it a priority as the founder to first have the founding team have a diverse perspective, have your executive leadership, you have a diverse perspective, having your board have a diverse perspective, what I really love and double click on bringing to the boardroom is a diverse perspective, myself, being the only female in the room and most of the time is a powerful thing. And I really hope that that can trickle down.

 

Jess Mink  

And I think it’s really important to set those people up in up for success, right? Bringing in different voices isn’t enough, right? You also have to give space and listen to people and encourage that different voice, right? Because it’s really easy to accidentally shut down that difference and technically have a wide range of people at the table but only be hearing the majority thoughts.

 

Tess Hatch  

Jess, I resonate so much everyone talks about DNI diversity and inclusion, but I think they’re missing the third piece, which is belonging. So great, you have a diverse perspective, you’ve included this under represented or previously, I like to use the acronym hugs, historically underrepresented groups, so we can call them hugs, fun fact, a member of hugs. But then you need to set them up for success, you need to make them feel like they’re part of the team and support them. Absolutely.

 

Christian McCarrick  

As someone who advises companies and as on boards, is there anything explicitly now that you do in guiding some of these founding members to as they’re building out their executive team to bring this to the table?

 

Tess Hatch  

Absolutely. One, I talk to all of my CEOs that this is important, it should be a metric that they set and track just like they would their revenue or any other thing, and it’s just as important. Secondly, I personally think being on the Comp Committee is incredibly important regarding making sure that people at each level of whatever their background is, are being paid and are getting the same amount of equity. That’s incredibly important to retain these people. Fortunately, every situation where I have either advised or voice my opinion, actually, it was the entrepreneur voice, and you’re advising me on how important it is for them. So I’ve been delighted with how onboard and how actually everyone really recognizes that this is important. It’s a problem and having a game plan or a roadmap on how to solve it. That’s a lot more difficult. 

 

Christian McCarrick  

Yes, yeah. 

 

Jess Mink  

And one thing I’ve noticed is that if you do the work for inclusion, it often actually builds a better culture for everyone in the company and forces a higher level of organizational maturity, right. Like some of the basic things, I always like to bring in our career ladders and salary bands and explicit ways to get promotions, right, which helps everybody.

 

Tess Hatch  

What’s a career ladder?

 

Jess Mink  

Yeah, a career ladder is a description of what it means to do each of the levels of a job, so that people know what they need to do to get promoted. And I think they’re one of the most powerful cultural tools we have, because you can actually embed the company’s values, including inclusion in the ladder. So it’s like to be promoted to be a senior engineer, you have to be aware of how much airtime you take and to make sure everyone in the room is getting having their voice be heard, right, you can build that into the job description, which is so powerful.

 

Christian McCarrick  

And to second that, and to expand on that. And the one thing that’s also important from a career ladder standpoint, in engineering, traditionally, it hasn’t been the best path forward for engineers to go get promotions, it was single tracked. So if you are the best engineer, the only way for you to get more money, more stock or more accolades in a company was to be promoted to a manager, right. And a lot of times your best engineers might not make the best managers. So what’s been really popular now, on the engineering fronts is having the dual track career ladders, right? So you have the equivalent of, you know, a director level is the same as a, you know, a staff level sort of engineer at a company or principal level engineer company, depending upon what you do. So that their patient equal, the seniority in the company should have equal the leadership qualities of each should be equal, although one might not be, you know, managing, but they should sphere of influence and, you know, respect that, that matches, so we don’t lose a good engineering gain a bad manager, right? Which happens.

 

Tess Hatch  

It’s awesome, the ability to still vertically integrate, but as an individual contributor, and bring as much to the table as others who are managing people, it’s a different type of skill set, none are better than you guys are just different.

 

Christian McCarrick  

And it helps with retention, right? Because you don’t want to lose your best engineer, because you don’t have a manager position for them. And then, and then the kind of Peter Principle kicks in, you have people who just they’re just they, they get promoted to their excellence, but their excellence is technical, not management. And the other thing that we talked about a lot, which is I think, equally important is giving people the ability to go into, say, a management or leadership career track, and then have them be able to go back, right? And the ability to do that if you go back, it’s not like you failed as a manager, right? You’ve helped out for a year, right? Or someone went on leave for some reason, and you stepped up and you realize, “Hey, I learned a lot of good things doing that”. But now I want to go back to an IC, right? And as a manager, I love managing employees who’ve actually done both because they get it right, they tend to get the challenges more of having seen both sides, right? It gives them an empathy that they wouldn’t have otherwise.

 

Jess Mink  

Yeah, I feel like one of the big differences between a junior engineer and a senior engineer is how much they understand the business and the context that they’re working in. So that they’re able to understand the problems and how that relates to different priorities, which having a stint in management is a good way to do that. But definitely not the only way if that’s not something that’s calling to you.

 

Christian McCarrick  

So one of the things test, as you advise companies, as you look into investing in them, are there any things that you feel it would be important for, you know, managers, or founders of companies to kind of know, walking into it, right? Is there anything that you see as a theme that people tend to, or it’s just all over the board? Like, I wish everyone had these three things, they knew these things before they started a company or as a board. These are the things that you think are important at early stage companies.

 

Tess Hatch  

For a founder that is pitching their company to any venture capitalist, there’s fundamentally four things that I look for. The first is the problem. How large is that problem usually measured as a total addressable market? The second is the solution. What is unique about what they’ve come up with that solves the problem? The third is, who cares about the problem? So the customers and how much are they going to pay for the solution. And the fourth is them the team, what’s unique about them, that they can one, or the best to solve the problem, and then to really understand the solution. And those customers. And that fourth one is, is by all means be most important, it’s the team, it’s really you venture out, start really investing in people at an early stage, even throughout the lifetime of the company, it’s if it’s the right person and team at the head of the company is going to steer the ship in the right direction and be able to build the organization necessary to solve that. So one, two, and three really come down to four, it’s a problem solution and customers is all dependent on that team and and how they articulate that how they think through things, etc.

 

Christian McCarrick  

So what what do you think now, once they’ve kind of maybe you’ve made the investment now? And what are the important things as they’re growing and scaling the business that you think it’s important that they should keep their eye on?

 

Tess Hatch  

Product market fit for an early company, is the most important thing.Who is your customer? and continually having those customer interviews talking to those people, some red flag? Or is is I’m going to build this because I know that’s what they’re going to want know, talk to them, ask them what they want, build exactly what they want. Is this detail, do you want it red or blue and ask I just think continually having the customer in the loop, knowing who that person or entity is and what they want, especially at an early stage and continually talking through that. Once you have product market fed, the other things will will fall into place.

 

Christian McCarrick  

I think that’s a great point. And especially if you get some technical founders, a lot of cases, we know what the customer wants, or I think I know best right? And really getting that product market fit is is so important. And not just I think to start, right, because I think the challenge as companies scale is to make sure right, maybe you’ve crossed that chasm, right? And you have that initial product market fit. But then what’s next, right and not falling into that the laurels of Well, this was our one product, and how do you evolve?

 

Tess Hatch  

Absolutely, you need to continually iterate. And there’s such thing as a product roadmap where you’re going to have a whole lot more in your future of their either versions of the product iterations that expansions, and continually knowing your market, knowing who you’re selling to and what else they want next. Absolutely.

 

Christian McCarrick  

So I think you know, Jess, I think this is important thing, too. When managing teams and engineers who sometimes get dis maybe distracted with the shiny, cool, technical thing, right, but as an engineering leader, how do you find is the best way to bring engineers and engineering leaders and other managers into that product? market fit conversation? Right? It’s a little bit of the why, right? How do you help them explain the why of what they’re building?

 

Unknown Speaker  

Yeah, I thread the way through everything. When I’m working with engineers. It’s one of the pillars of the career map, right, that we just talked about. It’s also something I talk about in one on ones and I coach people in. I ask engineers to go along on customer interviews and talk to customers, as well as customer facing people inside the company, like sales and support. Support is often a goldmine of information that’s ignored, as well as sales engineers. Right? Those are two huge sources of information. And then I also talked to the engineers a lot in terms of the problems I want them to solve and the impact I’m looking for, instead of the feature I want implemented. So once they’ve implemented it, I actually asked engineers to demo what they built. And as part of the demo, tell the story is that how this solves problems for people in the wider world. And then when we go back and collect those metrics, we can prove it was right or that we missed and then have another iteration at fixing it, or letting it go.

 

Unknown Speaker  

I mean, I think that’s another thing that a lot of engineers sometimes get very attached to things they’ve spent some time on, they tied into their personality and where they are. And I think it’s important to understand that if the product market fit is shifting, or the customer base is shifting or evolving, that it’s important to iterate quickly, right, but be able to also look to see, this is working, let’s focus more on this. This is really not working. It’s okay to let things go. Right. It’s okay to not chase that good money after bad,

 

Jess Mink  

You know, and that’s a good point, the majority of ideas that seem like they’re good are terrible.

 

Tess Hatch  

So how do you choose? You said customer success or sales, they have this abundance of information, because they’re talking to the customers and customers want everything under the sun and some. So how do you then determine which one is the one that you really should then have your engineers go and solve and then tell their story on how they…?

 

Jess Mink  

Yeah, so I often when I’m thinking about customer problems, don’t build exactly what the customer asked for, I often look for the problem under all the solutions that have been offered. Because often the user will suggest a bandaid to fix their immediate pain. And if you look at the whole scope of the suggestions, you can see that there is a fundamental missing feature or problem or a workflow that can be shifted. So that’s the first thing I’ll try and look for, is there a deeper solution? And obviously, if I have an idea of a deeper solution, I have to validate that that’s paper prototypes and like, does it work? Or am I just making things up? So the other part of it is, I’ll look at the addressable market you were talking about, right? Like what type of customers are asking for this? Is it a few really loud customers? And if it is, how strategic are they? Because maybe you still want to do it? Or is it like your silent majority is actually feeling this pain really deeply, but not being super loud. And people have picked up on it subtly through solving other bugs, right, and it’s come up inside conversations. So figuring out the percentage of customers and the impact of that customer segment,

 

Christian McCarrick  

And I want to pivot a little bit back to something you said Tess, and as we’re going through engineers, engineering leaders, CEOs of companies, I think there’s been a resurgence to, or at least a spotlight on the importance of good leadership in companies, right? Not just we’re going to throw a couple of engineers at it, we’re going to build something but the concept of building strong cultures, as you mentioned, and building strong teams and healthy teams is important. How often do you recommend to new CEOs and new exec teams to get executive coaching? and and you know, help to guide them through the softer side of the business goes

 

Tess Hatch  

All the time. Back to the question you asked earlier about, what are some of the important things that you sit down that first board meeting, you make sure you have product market fit on a company stage, but I highly encourage each of my CEOs to a few things. One, work with an executive coach. Two, be part of a CEO group. So being up there, it’s it’s a very difficult and lonely job. And you’d be surprised how many CEOs feel the exact same way. While you could be working on totally different companies in different industries, you can relate to one another. So being a part of a CEO group, and you can talk through various team dynamic challenges, or how do you price this or how to fire someone and these things with your peers is so incredibly important. So absolutely, I think those are the skills are hard, and working with a coach or other people that are going through that with you, you can gain so much.

 

Jess Mink  

And you really don’t need to wait till you’re at the CEO level to build that network of peers to right at the exact level, it’s super important, because you’re the only person in that job in your company, right? It’s also really lonely. And then you can start getting used to that at the manager or even senior ice level, because that’ll bring you different perspectives from different companies. And then you’ll have different insights to bring to your company, which will add value.

 

Tess Hatch  

Riffing off of that, you don’t have to be a CEO to have what I like to call a professional board of advisors. Every single person should have in their career, three to six people that you go to for various things. And I also think it’s important, I have a matrix where I list who those people are, and sometimes they change throughout your life. So I list who I have that I can think of, and their genders, their age, their marital status, their radars, to make sure that the people that I’m going to our first diverse themselves, and are helpful for different things. So I have on that some of my engineering professors from my graduate degree at Stanford, I have venture capitalists who are very high partners at their firm and are now retired. I have people from internships decades ago that have known me for a really long time. So this professional board of advisors you can have, wherever you are and whoever you are at your company. But it’s so important to have a group of people that you can go to for these either career or life decisions to chat with.

 

Jess Mink  

Absolutely. And one thing I found really useful when I’m thinking about roles I haven’t been in yet, is to go into the different slacks and online forums. And you can join them for roles you’re not in yet. And you can watch the chatter, the pure chatter of people who are in those roles and what types of problems they’re wrestling with, which lets you walk into that role, eventually much more prepared, because you know, what the common problems are and what the common solutions are, even if you’ve never done it before.

 

Christian McCarrick  

So some of the takeaways, I think, for this for, for the listeners here, having a coach, I think at all levels, whether it’s maybe not an executive CEO, but getting some coaching, some mentoring, super important, I think it’ll help in your career. What was the terminology again?

 

Tess Hatch  

Professional board of advisors.

 

Christian McCarrick  

Thanks, Tess. Yeah, I think that’s such an awesome thing. But sometimes technology, people tend to do too much ia focus on having that maybe in just technology. And although there are some very specifics to technology and technology leadership, running a company scaling teams, there’s so many similarities outside of technology, right? So for my listeners, really reach beyond your circle that you might have that might be very limited, to your point actually be very explicit about who I’m looking for. There’s a big gap here, I don’t have anyone from a large company, I don’t have anyone from this diverse background, and making sure that you’re very explicit about that. So I think those are really important things.

 

Tess Hatch  

Being explicit. These people know they are on my professional board of advisors, I explicitly asked them, there is nothing wrong with asking, Hey, will you be my mentor? Can I go to you when first? I’ve never heard someone say no, it’s nice. It’s flattering, it says, but sad. Secondly, I also offer how I can be helpful in return. It can be literally as small as remembering when their birthday is sending them a card. Or dog sitting their dog to “Hey, I can help you with providing deal sourcing for your company” when I was a student or “providing you updates with how the space industry is going”. But no explicitly asking, “Will you be my mentor?”.

 

Christian McCarrick  

And the peer groups are very important to as you grow, I think this is what happens when you come from an from an icy individual contributor engineering, that’s your first and you go into management, I think that’s your first taste of what’s a little lonelier, because now you’ve had some former peers, and maybe they distance them from you a little bit or you feel like you can’t talk to them about everything like they used to. And then as you go up, and even for as you go up the ladder, and as VP of engineering, who typically now reports into the CEO, a lot of times the CEO also isn’t technical, right? So you have that same concept. Well, it’s lonely, you have a peer group. But there are certain technology challenges that I think it’s also important for each level at that stage to have a sort of peer group that they can go to, to talk about, you know, I have one and it’s it’s the best thing. It’s also one of the reasons why I started this podcast, because I get to talk to people like joke, it’s my sort of therapy session where I get to also see that while I’m not the only one going through the struggles, and everyone seems to be going through this and it makes it takes that weight off your shoulder when you know you’re not the only one.

 

Jess Mink  

Being explicit about that peer group can let you get closer to people you admire, right? If you say, “I have a monthly breakfast, I would be really honored, if you would like to be a part of it, I think you could get a lot of value from here’s the other people in it”. So it’s a way to move an acquaintance that you met at a meetup closer into someone that you can really get advice from.

 

Tess Hatch  

You said, the peer group feels like a therapy session. And sometimes a therapist is really helpful in the mix as well. And I think that’s very undervalued. And sometimes I not spoken of in this industry or life. But I think that is so important.

 

Christian McCarrick  

Yeah, mental health is a huge thing that doesn’t get talked about enough. I think that’s a whole other episode. Right, which I’d love to have a conversation about. It’s kind of near and dear to my heart to without going too deep into it because of Auth0 is a predominantly remote company too. And there are other challenges that people face. And I’ve talked with with other leaders of other remote first companies, where being remote you there’s some challenges of being lonely and how you compensate for that. Love to chat about that another time too. One of the things I want to I want to talk about to as well is we mentioned it early in the beginning, diversity inclusive it right, what are as a VC, one of the things that you talked about was, it should be tracked as a metric. Okay, so clearly, how do you start tracking what you have currently, right? Because you can’t look to see what you have? Is it a problem? Is that not a problem? How do you work to improve unless you have some data? What are the important things metrics, you think you should track?

 

Tess Hatch  

Absolutely. Coming into a company, you can easily aggregate the data of the company’s current team. And once you level set where you’re at where you want to be. So first deciding 50/50 male/female, let’s use that example. And then setting a goal for achieving 50/50 male/female in a year in two years and three years. Of course, this is all dependent on the denominator, how many people you start with and how many people you want to grow to. Now once you set that goal, step two is achieving that. So people will apply to your jobs either listed on the website, or the recruiters that you’re reaching out to. And if you eliminate bias within the interview process. So if you’re having 50/50, male female applying to the position of in the first place, if you’re eliminating bias throughout the steps, you will ultimately achieve your goal. So an example of this is the violinist auditions, where they pulled a curtain and actually asked the male and female violinist to take off their shoes before walking across the stage before their audition where the judges cannot see who was actually playing. And before this situation, historically, males would always be the first or second seat when the study was performed, and they couldn’t hear the clicking of the females heels walking across the stage, it became a lot more equal. So setting the goal and then a limiting bias within the interview process or selecting who that person is, is the two steps that I would recommend. 

 

Jess Mink  

And I’ve noticed in engineering sourcing, you’re not going to get equal representation just from posting something on Stack Overflow or your company website. There’s gender differences and racial differences in how people look for jobs, right, there’s a lot more working through networks and making sure things are safe, if you’re a member of an underrepresented group, because you’re not necessarily able to take as many risks or the cost of taking the risks is higher. And I also wanted to talk about how bias in the interview process can be a lot more subtle than knowing who it is you’re interviewing. It can also be structural things like how much time it takes to do the interview, or what times of day you’re hoping people will be available. So there’s a lot of different factors to consider. 

 

Tess Hatch  

Tell me more about that the time of day of the interview?

 

Jess Mink  

Yes. So if you try and schedule something for when someone might have childcare duties, or if someone has another job, right? Like it’s a privilege to be able to quit your job, and then job search as your job versus having to Job Search while you’re in a job right, which will be more limiting. So structuring your interview process so people can be available when they’re when they are available, because you don’t know what the constraints on their life are.

 

Christian McCarrick  

you yesterday about sourcing. So what are the other ways that engineering managers and leaders can help to look for to increase the funnel of attracting some more underrepresented groups and a talent in that pool?

 

Jess Mink  

Yeah, this is one of the things where you get a virtuous cycle. Because the more people from underrepresented groups you have in your company, the more people will apply, because there is a big whisper net and people do a lot of back channel validation. If you’re trying to start that up, you’re going to have to put in way more effort. There’s a great website called hire more women in tech. And I really caution against focusing only on gender initially, because it’s so easy for DNI to be white women feminism, right, you really need to focus on many different underrepresented groups at once, initially. The website has some really great thoughts to counter that people might have in their head, as well as some really tactical things to try. There’s also different jobs boards that focus on different groups. Again, and if you can plug into different professional networks that are targeting different groups, that’s a way to get the job descriptions out there.

 

Tess Hatch  

There’s so many different types of diversity, there’s I like to use the analogy of an iceberg. Only 20% of an iceberg is actually above the surface. So things you can see. What gender you are, the color of your skin, how tall you are, etc. 80% of the iceberg, which is all diversity is maybe you were the first one in your family to go to college, maybe you were the first one your family to be born here. Your socioeconomic status, how you were raised, you nurture all of these other things are our diversity as well, which absolutely, you should, just like you said, a KPI or a metric to have 50/50 male/female, you should set these metrics for race, ethnicity, and other under the iceberg things that you can’t see as easily but classifies diversity.

 

Christian McCarrick  

And I think one of the things that’s important to look for as well is that you want to make sure that you have equitable distribution at the levels in your organization for members of underrepresented groups. Right. So having a high level, but they’re all the most junior, you know, you also want to make sure you put members of underrepresented groups and support them get growing into senior roles and organizations as well. Right. So how do you help make sure that you have that balance equal across all the levels of your team?

 

Jess Mink  

Yeah, absolutely. And obviously hiring senior people, they have more options. So you’re going to have to put more work in. And I think fundamentally, for people to succeed, once you’ve got them in the door, you need to have done the work, right? from basic things to making sure you have a good family leave policy to making sure you have gender neutral bathrooms, so much more complicated things like making sure everyone’s voice is actually heard, making sure credit is given, making sure you have good employee resource groups, so many little things right, actually taking micro aggressions seriously. And if you take that seriously, and you’re out there championing that, then when you have conversations with senior leaders, they’re going to know that like people talk, we’ve all heard stories about different companies, and especially a senior leader is really unlikely to join a company without having done due diligence from some of your current employees.

 

Christian McCarrick  

And I think I want to point something out to that, for engineering managers and leaders of companies that addressing the imbalance that we have today is not incumbent upon the members of the underrepresented groups that you have in an organization. Right? It is, just because you’ve hired someone, they don’t become the token champion for that, right. This is an effort that needs to be led by your entire organization, from the top down at every level and making it a priority.

 

Tess Hatch  

There is a definition called feeling tokenized, where you are now responsible for your entire fill in the blank, where you come from. And it’s absolutely so important to not have that responsibility lie in their shoulders, and then to shine on others, and help spread across that responsibility.

 

Jess Mink  

Yeah, relatedly, that work, the work to actually make the workplace more inclusive, which creates better diversity, which creates better business outcomes is usually not recognized or rewarded, and companies. So it’s really important to set up structures that recognize that. And when you’re interviewing people ask them about that work, because it’s probably not on their resume. And it may have been incredibly impactful, really difficult work. That’ll give you a lot of insight into how they approach other problems as well.

 

Christian McCarrick  

And one of the things I’ve heard in the past two is the concept of sponsorship. Right. So how do you recommend and how as an engineering leader would you recommend maybe sponsoring someone that is a member of an underrepresented group that you would like to, you know, see growth throughout a company?

 

Jess Mink  

Yes, so first, I’m going to define sponsorship in case anyone listening doesn’t know what it is. Sponsorship is kind of like mentorship, and that you might be providing advice and you’re invested in someone’s career. The difference is, when you’re sponsoring someone, you’re putting your career and your credibility on the line to give them more opportunities. So giving them speaking slots, nominating them behind closed doors for that new manager position, right? All those little opportunities, you have to push someone’s career forward. And if you don’t think about it consciously, and you’re not explicit about who you sponsor, you’re most likely going to sponsor people who are like you. So it’s really important to think about sponsorship explicitly, and then explicitly choose people who aren’t the majority of the demographic of the team to sponsor.

 

Tess Hatch  

Thank you for defining that. I have not heard of this before. Although I feel very fortunate that I have personally been sponsored by many of my colleagues and partners here at Bessemer. By other people in the venture capital or space industry, where historically, it has been a very similar type of person speaking at Space conferences, and always being now invited and included to provide a different perspective. So I had not heard that before. super interesting. I love that and will now actively I, when you define and put it out there, it’s it’s a lot easier to say, Okay, I can absolutely do that and return the love.

 

Jess Mink  

That’s amazing. Because the more senior the people who are explicitly sponsoring, the larger the impact that’s going to be because those opportunities are so much rare.

 

Tess Hatch  

Absolutely, you can feel championed, but then you can also really push and feel sponsored.

 

Christian McCarrick  

Great. So and how do you is that something just that? How does that originate? Is it from the sponsee like asking for help? Or is it from maybe a more senior manager actively reaching out or combination of both?

 

Jess Mink  

Yeah, it can be instigated any way, but the senior person, it really has to believe in the other person. It’s not like a mentorship role where you’re like, yeah, sure, whatever, I’ll mentor you, because you asked, right, you’re putting your career on the line for the other person. So you have to legitimately believe in it. So fundamentally, this decision lies with the senior leader.

 

Tess Hatch  

So if I’m your employee, or you’re my manager, how do I convince you or get you to sponsor me?

 

Jess Mink  

Yeah, I mean, you hired me. 

 

Tess Hatch  

That’s a lot. Now, I want you to not only manage me, but I want you to now be responsible for my future trajectory.

 

Jess Mink  

Yeah. And I think this really segues neatly into managing up, right. So people talk a lot about managing down. And sometimes people talk about first team, which is the sideways. But managing up is super important, even before you’re in a manager role. And what managing up is, is setting expectations with your manager, asking for what you need, making it really clear where you’re trying to go and doing a reasonable amount of adding visibility to good work, you’ve done AKA bragging.

 

Christian McCarrick  

Which is huge. And at the talk I gave in June last year to lead Dev. It’s one of the things that I don’t think, well, some engineers are very good at bragging. But I think in general, and I had an issue with this myself early in my career, it was important for me to do the work. And that’s really that matter. I just did the work. People should know that. But know, people are busy, right? My manager might have lots of other reports, he has bosses he has to do with companies growing things on fire. And although they might know Yeah, Christians doing good job, but oh, wow, Christian was responsible for XY and Z that helped us do that. And I think also with members of some underrepresented groups, that they’re a little more hesitant to do that. So I think it’s very important to keep a journaling of the things that you do the impact that you had. And it’s okay to like to present that to your boss, right? It’s okay to present that. And to be a little little bit of the PR machine for yourself, right? I think that’s super important.

 

Tess Hatch  

The two things I’m hearing is one, humbly bragging, being able to articulate your accomplishments. But humbly so there’s, there’s a different way of saying I can run really fast, and I can run a mile and under seven minutes versus I run a mile under seven minutes. And the second one is explicitly stating what you want. I want to speak at that conference, I want to be promoted by the end of this year. And for hugs, historically underrepresented groups or minorities, it’s sometimes difficult to for them to verbalize both of these things. So having a medium and which they can write it down and share it is so incredibly important. 

 

Jess Mink  

And I think it’s important as leaders to solicit where people are going in their careers, and what they want to learn in the next month or two, because people may not be used to the idea that their manager can be useful.

 

Christian McCarrick  

That’s a whole nother podcast. Those tests of hypocrisy and everything else, right. The thing that as a manager, that’s it’s so great for me is if I go to my peers and say I want to promote this person. And the answer I get back is, of course, they’re not promoted already, right? So I think as as a manager, and you is your job, right? If they do a good job, and your managers do a good job of doing that internal PR and of letting people know, the impact they’re having, that when promotion time comes, it’s a no brainer, right? People are actually have people outside of the company of your team championing them for what they’re doing and their accolades that they should get.

 

Jess Mink  

Absolutely. And I think this plays in really clearly to why it’s important as a leader to make sure credit is fairly allocated when people because like, there’s a common theme where people will bring up an idea in a meeting, for example, and then someone else will reiterate it later. And the credit will go to them. So it’s really important as a leader to watch for that and shut it down immediately. Because the person standing in the company is really useful, right? It’s useful when you make a promotion case, and it’s useful for helping push their career forward. So it’s up to you to to make sure that that credit is being fairly allocated.

 

Christian McCarrick  

Well, great as a kind of a quick wrap up here. Some of the things I also ask after this really great conversation, I’m super glad we’re able to do this today. And I’ll ask each of you, and one because I’m just an avid reader, right, and I want to continue learning. That’s the other thing I try to tell the people on this podcast is always be learning, right? Because you’re never done. And no matter what it is you, you might learn how to be a better cook or something or in your career, but always learning I think opens up so many more possibilities for your life, but test for you. Anything that you you’ve recommended in the past something you’ve read recently, it could be a book, a podcast, a great blog post,

 

Tess Hatch  

I am a huge podcast fan. So my my favorite is the entrepreneurial thought leader series put on by Stanford, where they have all different types of backgrounds, from from entrepreneurs, to VCs, to executives to etc, and share their their story. And it’s not. We did some things. And now look, I’m a unicorn or a publicly traded company idea. It’s I was living in my car for that month, and couldn’t pay salary to my employees next week. And how I got through it. And it’s, I’m much more of a while I do love the books on here’s the 10 important things to be a good leader or how to negotiate. I learned a lot more from anecdotes. So whether it’s that podcast, whether it’s biographies or autobiographies from successful people, it’s very powerful.

 

Christian McCarrick  

Great. Yeah. Podcasts are awesome, especially for people commute and whatnot. It’s a good medium.

 

Tess Hatch  

Also, shameless plug, I write a comic called Adda ride, which is about a young female who travels to space with her robot assistant ons, and it’s about their adventures on and traveling to the International Space Station. So if you want to check out that, that comic, she has an Instagram and hopefully, eventually and a website. So encouraging young females who are interested in space exploration. 

 

Unknown Speaker  

Cool. Send me the link Tess. I’ll make sure I get on the show notes. I was gonna say the space notes. But you know, maybe that’s appropriate on the show notes. 

 

Tess Hatch  

You got it. 

 

Christian McCarrick  

Excellent. Jess?

 

Jess Mink  

yeah, the resources I keep coming back to again and again and again, especially when I’m working with newer managers. Some of them are the management books like Five Dysfunctions of a team. I don’t know if you knew but there’s a longer version and takes like an hour to read. It’s great. Just buy it. I also point everyone at Laura Hogan’s blog because she’s amazing anything she’s written about, if I read through what she wrote, I’m like, Yes, that just go do that. So those are two resources that I point people at a lot. I’m currently reading Dare to Lead. I’m finding it really challenging and evocative. So throw that one out there too.

 

Christian McCarrick  

Awesome. So I’ll make sure to put all these in the show notes. Simple leadership.io. For my guests, test, what’s the best way to if someone wants to reach out to you about, you know, going deeper on a part of the conversation we had today or just wants to reach out and chat?

 

Tess Hatch  

Absolutely. email me at space(at)bvp.com. Yes, that is my email. Clearly, I’m very passionate about space. So space at Bessemer Venture Partners bvp calm and I’d love to love to chat.

 

Christian McCarrick  

Excellent. Thank you Tess. Jess, for you?

 

Jess Mink  

Yeah, the best way to reach me is probably to tweet me at mink MINKJSJESS. Awesome.

 

Unknown Speaker  

Well, Jess, and Tess. I’ve had an awesome conversation this morning. Thank you very much for hosting at the Bessemer office test. And hopefully we can continue these conversations after this. Thank you very much.

 

Jess Mink  

Thank you, Christian. 

 

Tess Hatch  

Thanks.

 

Unknown Speaker  

Thank you for listening to this episode of the simpler leadership podcast hosted by me Christian McCarrick. If you’ve enjoyed the show, please subscribe. And don’t forget to leave a review on iTunes. Full show notes and additional information can be found on simple leadership.io. If you know someone who would be a great guest for the show, or you want to share your own experiences, please drop me a line. We’ll see you back next week for more technology leadership tips and advice as I interview more top software engineering leaders.

Christian McCarrick  [0:00]

This is simple leadership. Welcome.

Thank you to our sponsor Auth0 for helping make the internet a safer place by offering identity as a service and for supporting this podcast.

We’re here to learn from new and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams. Do you want more engineering management leadership tactics and information? Subscribe at simpleleadership.io to receive the latest updates from this podcast. Hi, I’m your host Christian McCarrick. This is the simple leadership podcast. Welcome back. Today’s guest is Jocelyn Goldfein. Jocelyn is an American technology executive and investor. She’s the managing director and general partner at venture capital firm, Zetta Venture Partners. Previously, she was a director of engineering at Facebook and Vice President of Engineering at VMware. On today’s show, we discuss culture, hiring, seeing things from an investor point of view and supporting women leaders in tech

Good afternoon Jocelyn. Welcome to the show.

Jocelyn Goldfein  [1:02]

Thanks for having me.

Christian McCarrick  [1:03]

Absolutely. And my one of my favorite things is obviously recording live with my guests. And we are in the we work at Montgomery station here in downtown San Francisco. So thank you for kind of making the effort and coming coming in here as well.

Jocelyn Goldfein  [1:14]

Well, it was a very long journey from my office, three blocks away in Jackson Square.

Christian McCarrick  [1:19]

Excellent. Which if you’re in San Francisco, one of my favorite areas on an anecdote reminds me a little bit of Boston. I went to school outside of Boston, the brick buildings and everything. Yeah,

Jocelyn Goldfein  [1:27]

Yeah, I feel it’s like old San Francisco. It’s really got the personality of the city. And it’s actually got some of the historic buildings that have survived even the fires in 1906. Yes, it’s a really cool part of the city.

Christian McCarrick  [1:39]

Excellent. So for those who are not from San Francisco next time you visit Jackson Square should be on the stop of your tourist destinations.

Jocelyn Goldfein  [1:45]

Absolutely.

Christian McCarrick  [1:46]

Okay. Justin, like I asked all my guests, a little bit of the background like how did you get to be where you are today because it is an interesting one.

Jocelyn Goldfein  [1:52]

Definitely some twists and turns. Probably like most of your guests. I spent most of my career as a software engineer and then a technology leader and it’s kind of quite a late career left turn to find myself here in venture capital.

Studied computer science at Stanford, interned at Netscape at the dawn of the web browser internet era, worked for a couple different startups in the late 90s, early 2000s, including co-founding a startup of my own, about 30 seconds before the funding window slam shut. So really not in the boom era, really in the bust era, when I started my company, and it did fine in the end, but I landed at VMware in 2003 was the tech lead of the device virtualization team. And that company, just when I joined was getting product market fit with the data center. So it was a rocket ship, we doubled headcount and revenue every year, five years in a row. And in that environment, if you can get your work done, you get handed twice as much work and so I rose through the ranks pretty rapidly took on more and more responsibility rose to the VP engineering level. And even when we moved to a business unit structure

 

became VMware first general manager of a business unit. In my case, the desktop business unit in 2010, VMware, you know, from my perspective had grown huge. It was about 10,000 employees then I had joined when it was a couple hundred. So I thought I’m not cut out for this big company thing. I’m going to go join a startup. And the most compelling founder I met was Mark Zuckerberg, and in 2010, I joined Facebook. And so it was a little under 2000 people at that point, and also growing quickly, not quite 100% every year. And so it had some scale challenges that I thought I could help with, actually. So for years at Facebook, that was really my exposure to modern AI and machine learning techniques. I think Facebook was an early innovator in that space. And my first big project was helping adopt machine learning for the newsfeed also worked with the photos team.

 

We got serious about computer vision at that time, and a number of the other product teams really helped a lot think through a lot of the sort of organizational scaling issues at Facebook, like how we hired an onboard engineers

 

culture. My last big gig at Facebook was running the mobile engineering team during our third and final pivot to mobile. And along the way, sort of my last year so at Facebook had started doing some personal angel investing. And I reached a point in my career, maybe it was a midlife crisis where but you know, all those years at VMware, it felt like a vertical learning curve. It felt like every year I was doing twice at my scope was twice as big, I was challenged twice as hard. I had to run so fast just to keep up with my job duties. And the first few years at Facebook were like that, too, because it was so you know, you couldn’t find two companies more different Facebook and VMware. They’re both as a part of the tech industry. And so that curve continued. And then the last year or so at Facebook, I really felt like I was working just as hard. The problems were sure difficult, but I didn’t have to learn new skills. I was applying skills I had. And so I had this sort of moment. At this point. I’m in my late 30s. And I had this kind of moment looking in the mirror thinking

 

Hmm, maybe my 20s and 30s were for growth and my 40s and 50s will be for applying what I have learned all along, but maybe I’m maybe my growth has got to taper now. And,

 

you know, not in terms of seeking the next title or promotion, but in terms of seeking more skills than I already had. And then I realized, no, it’s just like, this is what happens when you do the same job for 15 years. And you could go down one path, which is just total mastery, perfection, I don’t want to say by any means that I was the perfect technology executive or, you know, got nothing wrong or had nothing to learn. But I think that I had definitely done the 20% of the job that was the 80% of the skill set.

 

Christian McCarrick  [5:41]

Sure.

 

Jocelyn Goldfein  [5:42]

And I felt well equipped to tackle any tech executive job. And so I thought, well, I could spend the rest of my life really mastering that long tail last 20% or I could find a completely new job again, yeah, and I and I just instantly knew that that was what I had to do.

 

And so I really at first thought that that meant starting a company and becoming a CEO.

 

Christian McCarrick  [6:05]

Okay.

 

Jocelyn Goldfein  [6:06]

But having previously started a company in the late 90s, you know, I can be honest and say we started that company because we wanted to be founders because we wanted to be entrepreneurs. And in hindsight, you know, I don’t think that’s a great motivation to start a company. It’s like having kids to save your marriage instead of for the sake of having kids.

 

Christian McCarrick  [6:20]

Yeah.

 

Jocelyn Goldfein  [6:21]

And so I didn’t want to create a company for the sake of creating a role for myself, I wanted to only found a company once I had a mission I was really enthused about. So I thought, well, if I hang out a shingle as an angel investor, I’ll be in the mix with other founders with ideas I’ll be exposed you know, here at Facebook, I’ve got my head down every day I can’t think and so and so I did. I just left Facebook and I you know, composed a goodbye email saying I was off to be an angel investor and, and and I started angel investing and I spent a couple years doing that. But the more investments I made, the more I realized that the work I was loving what was giving me joy was working across a lot of founders was helping a lot of founders.

 

Christian McCarrick  [7:00]

Sure.

 

Jocelyn Goldfein  [7:02]

And I thought actually, I want this to be my work. And I thought about just continuing as an angel. I explored running a syndicate through Angel list and a few other ways, but I really wanted to be significant capital, significant backing, for founders and significantly involved in and really helping get lift for the company. So that led me very long story short into into venture capital and, and through a series of hard work and lots of time spent looking, you know, was was able to be in the right place at the right time.. And meet the team at Zetta and joined forces.

 

Christian McCarrick  [7:34]

Great. You do point out something else, right? There’s is a huge difference probably between although they are both fast growing companies, VMware and Facebook, right. Do you think they were mostly different because of the time frame like when they were created and when they launched or just the market, they were going after enterprise versus consumer?

 

Jocelyn Goldfein  [7:52]

I think that the fundamental differences between the companies I think it’s really Darwinian, it’s really evolutionary. I think we

 

adapt and evolve to suit our environment.

 

Christian McCarrick  [8:02]

Sure.

 

Jocelyn Goldfein  [8:02]

So, yeah, the founding teams were very different. You can find more different founders than Diane Greene and Mark Zuckerberg, but also, Mark couldn’t have started VMware and Diane couldn’t have started Facebook, right? Like, it’s like they were well suited to the problems they were tackling. And so yeah, absolutely. I think that the core axes of difference were the market they were in, and the technology stack  that they were built on top of them. And the constraints that that created on release process, which I think is synonymous with culture.

 

Christian McCarrick  [8:31]

Yeah. Yeah, absolutely. Now going back to early days at VMware, or whenever you started becoming the manager for the first time, having gone through lots of growth at VMware, and then a Facebook and then where you are now, do you look back at your former self and say, Oh, my, if you could go back in time, what were some of the things you would say to some of the people who are like listening to this podcast now that might be more early stage managers that are kind of getting into are people that are thinking about going into management?

 

Jocelyn Goldfein  [8:58]

Well, I actually started managing

 

At the startups before that I worked for before VMware. And it was very much the battle probably I think a lot of engineers have this experience. It’s the battlefield promotion, it’s sort of look left look right. The team so big, we need a manager and who’s going to be it? And lo and behold your it. And so at the beginning, yes. Oh, my just about describes it.

 

Since then, you know, I’ve obviously grown in my craft, as a manager, I’ve transitioned a lot of engineers into their first manager role and train and supported them. I’ve tried to give what I didn’t have, I didn’t have somebody to learn from really, because I was in this chaotic startup environment where my boss was effectively someone with no more management experience than me, or no more engineering experience than me or both. And I had the gift in the early days at my own startup, of a co-founder who was really wonderful and was sort of figuring it out side by side with me, he’s actually a dear friend, and you know, he’s in Texas, and I’m in California, but we still talk every month and he actually gave me a great pep talk earlier this week, and I’m

 

reminded of how much we learned together and how much I learned from him. You know,

 

what I always say when I transition engineers, to managers is I cannot teach you the motivation. You know, I think a lot of engineers fail at that transition. Because at the end of the day, you know, they spend all day in meetings and they feel empty at the end of the day, like they’ve had no impact. They haven’t created anything, you know, if your internal motivation is all to build, to accomplish something tangible, to satisfy your curiosity, you will struggle in the management role. But if you really care about your team, if coaching somebody else and watching them develop or seeing the team as a whole, accomplished something, ship something, even if you didn’t write a line of code, but you could feel some sense of proprietary responsibility because you have enabled it. If that intrinsically, you know, lights you up, then I can teach you all the skills. And the skills, our communication skills, their alignment skills, their conflict skills, you know, you name it, but they’re all just skills and you can learn them

 

and there is, you know, even books about them that you can read. And there’s communities you can join and wonderful podcasts you can listen to. But you have to start by caring otherwise, it is a thankless job. And if your motivation to become a manager is to get authority, control, ego gratification, or access to, you know, privy information, like those are very common motivations to become a manager, and they stink, they will not guide you towards doing the hard work that actually makes you good at the job.

 

Christian McCarrick  [11:02]

It’s really anti patterns for good management.

 

Jocelyn Goldfein  [11:15]

Yeah, I mean, just think about if you wouldn’t want that manager, don’t be that manager.

 

Christian McCarrick  [11:34]

Yeah. And I often say to sometimes the most successful managers are the ones that are more the reluctant manager, right? They’re the ones that well, they weren’t quite looking for it. But like I said, people just kind of go towards you or you become the de facto person for that and, and now you’re a manager. And a lot of times those people become more of that servant leader type manager to the ones that are what you talked about, like they want the power to control the the authoritarians, right? That’s right. Exactly.

 

You mentioned something to and you posted this on a tweet, I think that what is it? Is it motivation? is one of the secret under utilized management tricks or something?

 

Jocelyn Goldfein  [12:08]

Superpowers!

 

Christian McCarrick  [12:09]

Superpowers, yes, yes, yes. Tell me about that. Like, why is that so important?

 

Jocelyn Goldfein  [12:13]

You know, as engineers, we are actually used to problem solving. We’re used to identifying a root cause of a problem and proposing a solution. And, and we think of ourselves as rational. And, and it’s, it’s actually, you know, I think engineers have a lot to offer the discipline of people management because we know how to think about systems problems. We know how to think about inputs and outputs and side effects. And I think in some ways, organizational problems are usually systems problems. And I’ve found that, that my engineering lens, I can sometimes see solutions to these problems, that other kinds of managers come up with different solutions. And so having that diversity of perspective is actually really valuable. And I think very little of the kind of business school pedagogy about management comes from engineers so I think there’s like some books to be written there. But as an engineer, sometimes we lose sight of the fact that

 

And we’re not fully rational actors, we may be predictably irrational, but we are, you know, we don’t always behave the way you want us to behave or the way and but people do respond to incentives. And the thing is the percent incentives are not just financial. And in fact, it’s rarely the financial incentives that matter the most. And we gravitate towards doing more of the things that make us feel like we accomplish our goals and personified who we want to be and lived up to the expectations of people around us. And we do less of the things that hurt and feel bad and feel shameful. And so praise and encouragement, you know, is like sunshine to a plant like people just grow towards it. And so you know, when you think about ways to motivate people and like, explaining to them how important it is or how urgent it is or how much of the people need it or you know how glorious it will be your your bonuses attached to this like all those are

 

blunt instruments were giving people a reason to do something. But I think praise and encouragement people just grow towards they just crave. And it satisfies such a need people have. And it also engender long term loyalty in a way that other motivations don’t.

 

Christian McCarrick  [14:15]

And you talk about incentives before too. And I want to tie that into a blog post that you had written about culture, you sort of talking about, you know, culture is that what you you know,

 

incentivize right? and potentially disincentive?

 

Jocelyn Goldfein  [14:28]

Yep. The title of that post is “Culture is the behavior you reward and punish.”

 

Christian McCarrick  [14:32]

Correct. So let’s dive into that a little bit. What do you mean by that? Like, how do you reward things? How do you punish things go into a little bit of the the high level of that blog post you wrote.

 

Jocelyn Goldfein  [14:41]

Well, another common phrase people say is, you know, culture is what people do when no one’s looking. So it’s not, you know, people following an order. It’s people knowing what to do and they don’t have orders, you know, and how do people know what to do?

 

How do they evolve a value system? You know, and I think there’s this idea that that culture is just like this ethos or this mood.

 

Or these traits or qualities that people possess and we interview for those, you know, culture fit. And then if someone or fits our culture, they have those same traits, we bring them in. And then we all act according to those traits. And I think that’s just sort of silly because companies are pretty unique from one another. And humans are obviously portable between companies that have sure culture fit, like we can assimilate. And also culture can change over time as well. And so what is it that causes people really to behave in a certain way and to kind of go with the herd? And I think it’s that people want to feel good. They want to feel a sense of I, that they fulfill their identity, they want to feel that they fulfill their goals, and they want to feel like they’re doing the right thing. I mean, I think all of us, for the most part, think of ourselves as good people or not, nobody wants to be bad, but also we want to succeed. And so when people walk in the door, they look around, and they look at the behavior exhibited by the most successful people and it’s like, Okay, I’m going to do what those people do, I’m going to imprint,

 

Christian McCarrick  [15:01]

even if that’s different from say, What’s written on the wall,

 

Jocelyn Goldfein  [16:00]

oh, I think what’s written on the wall, like, you know, they say that like 90% of meaning in a conversation is conveyed in like body language and eye contact and like only 10% in the words that you said. And I think it’s the same with culture like, like less, we’re less than 10%, influenced by the poster on the wall. And we’re 90% influenced by what people actually do. And in fact, if the poster on the wall is contradicted by what successful powerful people in the company do, then we become very cynical about because of that mismatch, when they’re the same. We can actually get into the like cult like scenario where where people really embody and you know, bleed blue for their company.

 

Christian McCarrick  [16:35]

Patagonia.

 

Jocelyn Goldfein  [17:00]

bump you know, I’m going to try to succeed. Sure. But at the same time when I look around to figure out how to be successful and look at other people, I can’t judge their success by their compensation because I don’t know it. That’s right. So I’m going to try to copy the people who look successful based on title, scope of responsibility, possibly just swagger. Sure, like how much confidence they exude, like how much their culture carrier and get to sort of speak up in conversations influence influence. Yep. Yep. Like, like we cannot like humans are very highly attuned sensitive social instruments to sort of figuring out who’s got status. Yep. And so there’s all these written and unwritten status triggers. And we are desperately trying to be like the high status people and we’re desperately trying to avoid being low status people. And that will lead us to all kinds of things. So I think one of the lessons you should draw from this is like, be really super careful how you hand out overt status symbols, like a title or a promotion, because everybody else is going to emulate that. And if you think well, it

 

You know, the classic example is the brilliant jerk. This guy’s you know, our best engineer, he’s 10 times more productive. He solves the hardest problems, but he’s so crusty and mean to people. And we have a culture of being nice. But, you know, we really can’t deny him this promotion. He honestly, he’s a principal engineer, so we’re just going to do it. And you know,

 

we’re just doing it in spite of him, you know, violating this culture of niceness. So you elevate the brilliant jerk. Well, guess what the message you’re sending is that people who succeed in this company and get ahead are jerks. And so you’re actually encouraging other people and you’re in you’re supporting. And you might think, Oh, no, people, no, the poster on the wall says Be nice. So you know, they’ll just realize that he’s an exception. Yeah. And you think that but it people always attach more weight to the behavior than to what is said, Yep. And so so then they’ll just think, Oh, I can be really cynical about that. That nice thing is just lip service.

 

Christian McCarrick  [18:50]

Sure. Yeah. And one of the things we just started doing to at Auth0 too is building some of those culture and value things that we want to emphasize on into our career letters, things like

 

diversity and inclusion and things like span of responsibility and coaching and mentoring. Those are all things that as we look around for especially when you talk about senior IC’s who might not traditionally be, have thought about, well, I’m a senior technologist, but as you want that span of influence to grow with your organization, you want those people to emulate the coaches that you want to have mentoring and sharing and guiding and coaching because that levels up the entire org. Right,

 

Jocelyn Goldfein  [19:27]

You got it. I mean, I feel like there’s a pretty early divide in an engineer’s career when they decide if they want to lead or not, and it’s not do I want to manage or not sure like, you hit the point of scope where how big a problem you can solve your is maxed out by your typing speed. Yep, yes. And at that point, if you want to solve a bigger problem than that, and you want to make decisions that span more characters than you can type, then you’ve got to be able to influence other people to work with you.

 

Christian McCarrick  [19:53]

And you want those people to have the values that you want to have your company espouse.

 

Jocelyn Goldfein  [19:57]

Well, yeah, and at no point like when you were getting

 

Christian McCarrick  [20:00]

Your computer science degree or learning programming on your own, or however you got into this career. And probably your first several years in at no point did anybody say, oh, by the way, communication skills and teamwork skills are essential to your success, right? Like we’re told we have to be smart, and rational and objective and good designers and creative and builders. But we’re taught that this is fundamentally solo work. And it’s such a lie, right? Because if you want to do anything significant, what one person can accomplish on their own is pretty small. And so like maybe you can get sort of one leveling up in scope just by becoming better at what you do, maybe two, you know, step functions in scope. But very early in your career, if you’re going to go from being from rote work, to meaningful creative work, the crucial skills, actually, the soft skills that were taught to sustain or that at the very least, are neglected. I think for a lot of engineers that comes is like a pretty unwelcome surprise.

 

But you talked about earlier on about humans as system, right? And it’s true if you could have if you look at it like a machine and easy to instance, right? There’s only so much in here from one. But now if you’re horizontally scaling, just like teams, you can have that multiplier effect and actually now serve a much,

 

Jocelyn Goldfein  [21:11]

Much harder problem. Yeah, have much more impact. Oh, yeah. Oh, yeah. And it’s so powerful to be able to parallel lives that way and to be able to tackle larger problems and decompose them. But it means a commitment to building a skill set that you may have hoped not to, or that you didn’t, you didn’t enter this career thinking that you that your ability to succeed was dependent. On other on those Yes, exactly.

 

Christian McCarrick  [21:33]

Which is a great point, which is a whole nother podcast episode about things we should teach right to getting into, you know, CS degrees or other ways to be successful in our careers. Aside from being up the whiteboard really well and interviews, right? That’s a whole other thing, too. Speaking of interviews and hiring, you had written another series on you know, hiring. I’m still working on it. Yes. Excellent. One of the things that stood out was the screening process, right? And you talked to

 

How we think people in general are cutting too much from a percentage at this phone screen level, right? going to talk about percentages and why and you into this whole thing. So tell my listeners a little bit about, you know, what’s the genesis of it?

 

Jocelyn Goldfein  [22:12]

Yes, yes. So this all came about because I was at Facebook, and we were trying to really ramp up our hiring. Let’s see in 2011. So it’s towards the end of the year in 2011. And our hiring target for 2011 was 300. Engineers. We had failed, we only hired 250 and totally 250. Engineers.

 

until proven innocent. We want to be as selective as possible and hiring a bad engineer is so damaging and has so much impact on the team that like, we want to be sure we’re only hiring the excellent. And so you know, when in doubt, vote no. And so if you take people that you’ve trained to interview in that way about bringing people on full time, and then you ask them to start picking up some phone screens, well, you’re just naturally like a bias to say no at the screening stage.

 

Christian McCarrick  [24:25]

When you start the biases, like I’m it’s you said guilty until proven it is.

 

Jocelyn Goldfein  [24:29]

Yeah. Then what you get is, you know, look, if we could be certain that someone was a higher after a single 45 minute conversation, sure, we wouldn’t need to do this extensive interview process where we talked to them multiple times, right? And so nobody sure after 45 minutes and so that they default to know then like it’s no for everyone. And we had a lot of also existence proof that we were losing very high quality people at the screen stage because we had all these employee referrals that were going into the hopper and getting rejected were very high quality engineers could attest that this is an

 

at source. Yeah. Like, yeah, like they didn’t even make it to the on site. Right, God. And so Facebook on the one hand is sort of very firmly attached to its traditions and hiring, you know, is kind of third rail for most organizations. Because, you know, if you mess with it, everybody’s, in some sense, we can consensus agree on the hiring process we have, because it’s the process that hired all of us, therefore, it must be good. Right? And you know, and if we change it, we could hire a lot of bozos. That would be bad. So, or people we don’t want to work with. And so

 

Christian McCarrick  [25:35]

or people that are different from us, which is another issue.

 

Jocelyn Goldfein  [25:38]

Also scary. Yeah. So in a lot in any organization, it would be very difficult to tinker with the hiring process, especially in a way that says, Well, before when we hired you know, we were hiring five out of 100 candidates and now we’re going to hire 10 out of 100 candidates. Like that’s intrinsically scary, you’re lowering the bar,

 

because now we’re less selective. And in truth, no. What I’m doing is finding and fixing all the darn

 

rather than have like a big knockdown, drag out philosophical argument with people about change, you can say, Well, I’m gonna try a test. And it was almost, you know, at that time, I don’t know, I can’t speak for Facebook today. I’ve been gone five years. But, you know, at that time, it was almost holy like if someone was going to run a test, you couldn’t stop.

 

Christian McCarrick  [26:47]

Sure. That’s a good culture. Yeah.

 

Jocelyn Goldfein  [26:50]

Well, it really has been. And so I said, Well, I just decided to run a test. And so my test was, I took a bunch of people who failed their phone screen and I brought them on site anyway. And I mean, not like, blindly or randomly sure it wasn’t entirely fair test. But people were, I looked at the resume or I looked at the employee referral, or I looked at the contents of what was in the screening feedback, not just the bottom line decision. And I just put my thumb on the scales, and I brought them on site. Now on the one hand, like,

 

that’s ghastly. But on the other hand is not, I wasn’t extending a job offer to them. At worst, the downside was we’d waste the three hours that we spent in an onsite loop. And at best we would discover what I discovered, which is that the candidates I brought through had very close to the same pass rate, the same offer rate as the ones.

 

Yeah, so the phone screen like looked like it was working because it was taking the funnel and reducing it. Right. We went from 100 candidates to 27 candidates, obviously, it’s doing something effective. Yeah. But it turned out that it was wrong in both directions. Sure, right, because we still only made offers to a quarter the people

 

that it did bring, so it had plenty of false positives. But just because you have false positives doesn’t mean you don’t have false negatives. And so we had a lot of false negatives as well, the way that recruiters typically dealt with the situation that a good looking candidate got a no on the phone screen is they would do a second phone screen and try to get a yes with a different engine with a different engineer. Yeah, but not tell them like not build on the previous sponsorship, like a total do over Yeah, it’s like, if you had code that had a bug in it, you would instead of fixing the bug, you would completely rewrite the code. Right? Like it’s 100% more effort. Yeah, just to answer that one. You know, just to just to get out that, that one niggle of doubt.

 

Christian McCarrick  [28:35]

And it’s also important, I think if you’re going to do that, that you don’t introduce that bias from a one person already saying no, right?

 

Jocelyn Goldfein  [28:41]

So that was the argument for you was that it has to be a completely independent. And then if you get a split Yes, no. Then you get those people to talk to each other and argue about it. And like under some circumstances, the recruiters even went and got a third screen done. So it could be Best two out of three. And by the time you’ve done three phone screens that are each 45 minute our online interview was only four slots.

 

So what is the point of a screen anyway? It’s not optimizing for the quality of our employees. That’s what we do in the onsite interview, when we decide about job offers, all a phone screen is doing, it is literally just an efficiency slider. It literally exists so that we don’t spend four hours on someone we could eliminate with one hour. And so by the time you’re spending three hours to eliminate spending four hours with someone, you actually and so I just did the math on here’s the average amount of phone screen time we’re spending per candidate. And if we just loosened the threshold, if we just said, you know, what, if I think there’s even a one in four chance that really matter if I think there’s even a one unfortunate so this person could get thrown on site. In other words, I think there’s a chance they could succeed. Not I think there’s a chance they could fail. Sure, then I’ll send them forward. And so what that means is we do more on sites, but we stopped doing these second and third phone screens. Okay, when in doubt, we send them through and so we actually were net neutral on time spent. Okay, yeah, with all the extra on sites. We made it up in the

 

It was really embarrassing and awful to have a false positive to send through a candidate that people you respect have to waste their time on. And unanimously vote no. And you feel shame and guilt, right? Whereas, at Facebook because we don’t hire for our own team, we do a central we have a centralized hiring process in which engineers are sort of phone screen any candidate. And then when the candidates are hired, they go into Facebook boot camp, they don’t even pick a team until

 

Christian McCarrick  [31:23]

Google, I think, has a similar process, right?

 

Google

 

Jocelyn Goldfein  [31:24]

Google has a similar process. But Google at least last time I paid close attention. Google just assigned you to a team. Whereas at Facebook, you came into the onboarding program first. And at the end of six weeks, the candidate chooses the team, like the team is all common for you, and you pick the team you want. So it was a good system, but it had this flaw, which is that you know, unlike in a world where I’m an engineer on a team, and I’m screening people who are my own potential future co-workers, and they’re the reinforcements they’re the cavalry. Like I have a motivation to add to my team, because I’m because I’m overworked. And come help me I faced with that motivation didn’t exist. Sure, right, because it was very indirect

 

So you’re not interviewing a candidate for your own team. And on the one hand that kept you sort of objective and didn’t make you desperate and willing to lower the bar. But on the other hand, it gave you no positive incentive to take a flyer on somebody, you just had this sort of negative incentive that I’ll be embarrassed. If someone comes through that’s rejected. So we just had spiral, those bad incentives could have kept compounding and would spiral and spiraled into this place where the screen was totally ineffective. And so we fixed it. And we’re a ton more productive.  

 

Christian McCarrick  [32:29]

sort

 

Sort of general philosophy concept, when you talk about the two different types of interview like Facebook, and Google during sort of an interview panel that is sort of independent versus manager, hiring manager, actually, your team members trying to hire their team. You also work with other companies now, what are the pros and cons of doing it one way or the other? And do you actually recommend one way or the other now?

 

Jocelyn Goldfein  [32:51]

Yeah, I mean, VMware was very much the classic model where a hiring manager hires for their own team. So I’ll call them centralized and decentralized.

 

Campus recruiting tends to be centralized even at companies that are otherwise decentralized. So the advantages of the decentralized model, every hiring manager for themselves is the hiring buck stops with somebody like the hiring manager has the right alignment of incentives to work hard to spend time hiring, because they get the benefit of it. And to make a really thoughtful, nuanced decision about who’s going to work with you, and also to bond with a candidate and can persuade them to come work for you to help sell right to sell to close, like Don’t forget, when we’re interviewing, it’s a two way street we got close to and so it’s better for making hitting your targets. And it’s also it’s probably better for fit. And it’s mostly just better for your accountability. And it’s better for people who do the interviewing work to feel that it has that it’s rewarded.

 

Unknown Speaker  [35:35]

actually that you can deploy your whole workforce. So hiring goals are distributed unevenly between teams. The teams who need to hire the most are this hit with the heaviest workload of hiring in a centralized model, you can you can actually load balance the teams who have the most time contributed and the teams who have the most need receive the higher sure, but a disadvantage. A really significant disadvantage of the centralized model is there is no hiring manager taking responsibility. And it both Facebook and

 

Jocelyn Goldfein  [36:00]

there has been a tendency to make recruiting the responsibility of the recruiter rather than of the engineer, which I think is toxic. Sure. Okay. What I actually love the most, and I’m not, I’m never a one size fits all advice person, I always think it depends on your situation in your company. But what I love the most is a blended model, which is largely centralized, but with particular hiring managers taking responsibility for a particular hiring target, and they go and they go work just as hard to hire that 10 engineers as they would if those engineers were joining their own teams. And you’ve got to structure responsibilities and culture and reward and praise and all the other things so that they feel as rewarded for that as they would if their team desperately needed 10 people got them.

 

Christian McCarrick  [36:41]

Sure. No great, great discussion on that. Shifting a bit now putting on your kind of venture capital hat. As you look into startups and other companies, is there any advice that you would give to engineering leaders at these companies that you just wish they paid more attention to, or wish they knew, or just something about could say, it’s not all about this, or technology or engineering, like pick your head up? Look around? Any advice for engineering leaders coming from the from the VC side?

 

Jocelyn Goldfein  [37:08]

It’s so funny, because I feel like actually, the commonest requests that I get from startup founders is can you help me hire my first head of engineering and, and, and that request comes about, of course, usually, because something’s going wrong. It just changes with phase and the birth of a startup, you’re not a company and you’re not trying to build for the ages, you’re just an engine of discovery, you’re just searching for product market fit. And that’s going to involve lots of backtracking, and you need as much feedback as quickly as possible. So as lousy as technical debt is, it’s generally by and large, it’s, it’s fine to accumulate a lot of technical debt early on, because honestly, the half life of the code you’re writing is a year or less, it’s going to be gone. So perfecting, it doesn’t matter if it was the wrong code to write if it was the wrong product to build. I think that this kind of the lean ethos has kind of gotten that message out there pretty thoroughly. But it’s still sort of easy to preach and hard to live. I do think though, there comes a point where you hit product market fit, and now you’re sprinting to satisfy as many customers as possible. And then what happens is you accumulate technical debt very quickly, and knowing when and how to sort of advocate for paying down technical debt. So you can speed up engineering, productivity is just an art. It’s totally situational. But But I do spend a lot of time counseling technical founders on like, when to make that call,

 

Christian McCarrick  [38:24]

and how to do it, because I think that’s something that engineering leaders, they just can’t say we’ve got a lot of technical debt, we have to pay it down, right? That that won’t fly at an executive team, right?

 

Jocelyn Goldfein  [38:32]

If the startup is 20 people and the CEO is also struggling, yeah. Or if it’s 50 people and the CEOs technical it can. But it’s engineers are prone to like technical, that’s just ugly to us when we want to fix it, because it’s an aesthetic problem, but also because, like it’s slowing us down. And it’s grungy, and it’s like working in a kitchen where every counter is covered with dirty dishes, like it’s just hard to work. But I think many CEOs have been burned with the engineer saying technical debt, technical debt, technical debt, and so then they take a quarter with no new features. And then at the end, the engineering team is no faster afterwards than before, because we rewrote the code, but we didn’t actually make ourselves more efficient. And so the other thing I would say is, the time to invest in technical debt is when you know you have the right product, and you’ve got to scale it. The other thing I would say is the time to invest in technical debt is when you actually have a solution that’s better, and for sure, will speed your team up afterwards. And you’ve got to be able to understand the cleanup, and explain the cleanup in terms of how you will go faster afterwards.

 

Christian McCarrick  [39:28]

Yep, what’s the ROI?

 

Another thing related to hiring related to culture, diversity and inclusion. I know that you also do work with female founders, women founders, and, you know, what are some things that CEOs can do startup founders can do engineering leaders can do to kind of really help embrace improving diversity inclusion in their organizations?

 

Jocelyn Goldfein  [39:51]

Inclusion is a function of your culture. Sure. And culture is created by the behaviors, your reward and punish. So guess what? people in positions change the culture are the people who are the role models and are and have the leavers of handing out status and rewards and punishments and firing people. So actually, CEOs and leaders are the only people and culture leaders, not just, you know, organizational leaders, those are the only people who can make the environment inclusive, like your diversity team can hardly do anything.

 

Christian McCarrick  [40:21]

Sure. The influencers? Yeah,

 

Jocelyn Goldfein  [40:23]

Yes. You know, there’s probably like a five step process of you know, the zero step is really assessing where you are, and whether your environment is inclusive. And if it’s not, what’s exclusive about it? And is that something you’re willing to change? Or is it not and just coming to grips with that. Or maybe there’s completely an inadvertent signals or something you had no desire interested in, you know, like this these few years back, I read this study, that’s like having Star Wars posters on the wall makes an environment, you know, less inviting two women. And I’m like, Oh, my God, that’s incredibly sad. I love Star Wars, when I see a Star Wars poster on the wall, like, I know, I’m among my tribe, and my people. Yeah, but like, that’s exactly it. It’s because it’s sending that clubhouse signal that makes you feel warm and belonging, but like, by definition, you feel belonging, because somebody else does not belong, right? There’s an in and an out group. And like, I don’t at the end of the day, I don’t need to tie my in group feelings of belonging to the movie Star Wars, much as it was the childhood favorite. And if doing that is keeping my team from being the best team it can be. And from hiring talent that I’m unable to hire right now then, like, I give up, I don’t need the Star Wars poster is not that important to me. So I think sort of things like sometimes there’s easy wins, you know, where it’s something that’s like symbolic and matters, but doesn’t really matter. And sometimes they’re tough. And you have to stick to your guns and say, you know, what, it is really important to us to have a no holds barred culture and that, like we allow swearing in the office, or we allow dogs in the office, right, this is a big divider. And you know, that means we’re not going to be inclusive to people with allergies, and we accept that trade off. Sure. Right. So you can decide. And then I think having made those decisions, you’ve just got to live them, and you’ve got a value, investing in diversity. I think when talking to engineers, I think there’s a subtext about diversity, which is, you know, I think all of us have the experience that we’re working at these high growth companies we’re desperately seeking to hire. we’re interviewing everybody, and we’re hiring everybody who’s above our bar. And so when we look at the result, and it’s only 5%, or 10%, female with the, you know, single digit percentages, black or Hispanic, some part of his is like, well, that must reflect the inputs. I know, I interviewed everybody who applied, you know, who had a good enough resume, and I know that I accepted, so like, to get a different population, I have to lower my bar, right, I’d have to accept people who right now are failing. And I understand that impulse. But I think it, it assumes a few things. First of all, it assumes that your interview bar is fair. And there’s like actually, a really data backed way to figure out if it is or not, which is to see how different populations make it through.

 

And  secondly, it assumes that the population who applies to work at your company is the population that could apply to work at your sharpening. And if you really value having a more diverse environment, and think it will help your company to have underrepresented people in the group to bring different perspectives and points of view, or to make it possible for you to hire more of them in the future, then you’ll go hunt them down. I mean, if you just sat there and only looked at applicants, you would never hire like that one signal processing engineer you needed. Or like, there’s always that one esoteric role, where it’s like, oh, I really need a network packet specialist and a networking specialist to if you know, who can do like, you know, Packet Inspection, and it’s like a very rarefied skill set, and it’s not there and your applicant pool, and you know, what you do you go source that candidate.

 

So you yeah, you’ve got to over rotate on finding candidates who bring things that your current team doesn’t have, and you’ve got to invest in that. And that does not require. So neither of those things requires lowering the bar.

 

Christian McCarrick  [43:58]

Just focus.

 

Jocelyn Goldfein  [43:59]

Yeah, just dedication. I think there’s also, I think, some tension around this idea that diverse teams perform better. So there’s lots of public evidence of this. There’s lots of studies know that public companies that have at least three female board members have better results, etc. Kinsey’s done a lot. But I think here in the tech industry, those are hard to take at face value. Because I think we can justifiably have some pride that our industry is one of the most successful industries of all industries, and that we have growth, that we have margin that we have, like the engine to make the world a better place for innovation, like

 

anything you could measure an industry on, you know, compared to, I don’t know, agriculture, politics, finance, whatever, like, I think we can justifiably feel some pride. And we’re also like, among the most images, yes. So if diversity is such a strength, why are we why is homogeneous tech better

 

than, actually those other industries are pretty homogeneous too,

 

but not as nice as us. Sure. So. And in particular, if we look at our most luminary companies, the most successful companies like remember culture is the behavior you reward and punish, homogeneity has been rewarded in the tech industry, it hasn’t been punished, like by performance. Sure. So this idea that we’re a meritocracy is like, a really powerful idea. And there’s the suspicion of hiring for any reason other than merit. And I feel that, actually, I kind of agree with that. And I think that most diversity advocacy doesn’t really come to grips with that reality. And so I think the principal position you can take about diversity and inclusion, and I do take it is that we would be even better sure if we were diverse. And moreover, I think tech, unlike other industries, is not a fixed pie. There’s just like a finite amount of jobs that can exist for lawyers, that is a function of total population size, there’s only so many lawsuits that can go on, there’s only so many contracts that can go on, it’s a function of how many entities exist. Same with doctors, right, like given a certain population of people who can be patients, we only need so many doctors and nurses. Tech is an unbounded pie. The more technically capable people we have, the more inventions we can create, the more value and wealth and impact we can have, the more tech workers we can absorb. So I would argue that even if you think tech is awesome, the way it is, if we could double the size of the tech industry and double the tech workforce,

 

to like who could argue with that?

 

Christian McCarrick  [46:20]

Sure. And the impact would be exponential

 

Jocelyn Goldfein  [46:23]

exponential. So whether or not you

 

think that like adding women and brown people to the organization makes it higher quality? Surely you can argue that like, okay, actually hitting my hiring target instead of half of it would be great. And by setting ourselves up in these exclusive ways, and by losing all that talent in the world, that could be exceptional tech workers, because of these social stigmas and stereotypes. Like that’s crazy. Like, we’re just we’re operating at half strength. Sure. So that’s been most of my belief most of the time is just that the argument is just for growth period. And like the obvious cavalry to tap, like, I think we found every white and Asian man who wants to be a tech worker as a tech worker by now. Okay. But like the obvious cap, the only place the cavalry is going to come from is we go tap into these people who are underrepresented. But I also in the last few years, with the rise of AI, and social media, the rise of the ethical questions around it, data privacy, I think all the social impact sort of knock on impact questions of what we’re building. I actually think for the first time I feel in my career, I feel like I can really point to a set of issues where I think if the leadership of tech industry were significantly more diverse, we would actually see these companies perform significantly better. I think think we’ve been blindsided and too slow, because we’ve been to homogenize at the top.

 

Christian McCarrick  [47:43]

Well, great insights. Thank you for sharing that. As we kind of get to wrapping up here, I asked all my guests, any recommendations you have, it could be leadership, Ai, books, podcasts, you know, anything that you have that you might recommend, for my listeners to, to absorbe that you think might help them?

 

Jocelyn Goldfein  [48:01]

Well, I recommend my blog, of course, in find it on Medium, my my spelling of my name is unique. I am a big fan of a book called “Influence” by Robert Chidini it’s not extensively about management, it’s very much about if you want to see humans as a systems problem, and you want to understand the inputs and outputs of human behavior. And you want to shed the delusion that humans are rational. This is a really good book.

 

Christian McCarrick  [48:27]

And we’ve pointed out they are not rational.

 

Jocelyn Goldfein  [48:30]

Well, I think we’re predetectable, but maybe not, it sort of depends on how you define rationality. Maybe I also really love a very old book from the 80s, which I think you can still find in a reprint on Amazon called “Debugging the Development Process” You know, there’s lots of books about management that talk about sort of the people and soft skills and coaching and their side of hiring whatever side of management, there’s very few that talk about the project management inside of our job is kind of dated, because it’s kind of back in the native software days. But you know, as much as it’s been written about Lean and Agile, I think this book is really unique and how it blends the people in project management responsibilities, and how those two things are actually inextricably intertwined. Like we don’t just have HR managers managing our teams, it has to be an engineer has to be somebody who can make an intelligent call about who should do what and whether they’ve done it correctly. Great. So that looks kind of unique.

 

Christian McCarrick  [49:25]

Okay. And for the listeners out there too you mentioned your blog, what are some of the best ways people could reach out to you if they wanted to contact you?

 

Jocelyn Goldfein  [49:33]

Well, I’m email is is probably the easiest way I’m Jocelyn at Zetta VP dot com. Okay, but you can follow me on Twitter, and LinkedIn connection. And yeah, I’m easy to find because there aren’t any other Jocelyn Goldfein’s in the world.

 

Christian McCarrick  [49:45]

Excellent. So I will put all those to listeners as well. I’ll put them on simpleleadership.io so you can actually see the links to these as well. Jocelyn, thank you very much for coming in today really had enjoyed my conversation.

 

Jocelyn Goldfein  [49:55]

I could talk all day about these topics.

 

Christian McCarrick  [49:57]

Okay, thank you very much.

 

Jocelyn Goldfein  [49:58]

Thank you.

 

Christian McCarrick  [49:59]

Thank you for listening this episode of the Simple Leadership podcast hosted by me Christian McCarrick. If you have enjoyed the show, please subscribe. And don’t forget to leave a review on iTunes. Full show notes and additional information can be found on simpleleadership.io. If you know someone who would be a great guest for this show, or you want to share your own experiences, please drop me a line. We’ll see you back next week for more technology leadership tips and advice as I interview more top software engineering leaders

 

Christian McCarrick  [0:00]

This is simple leadership. Welcome. Thank you to our sponsor Policy Room for helping make the internet a safer place by offering identity as a service and supporting this podcast. We’re here to learn from New and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams. Do you want more engineering management and leadership tactics and information? Subscribe at simple leadership.io to receive the latest updates from this podcast. Hi, I’m your host Christian McCarrick. This is the Simple Leadership podcast. Welcome back. Good morning, Scott. Welcome to the show.

 

Scott Carleton  [0:41]

Good morning, Christian. Great to be here.

 

Christian McCarrick  [0:43]

Absolutely. And Scott, where are you calling in from today?

 

Scott Carleton  [0:46]

I’m currently in New York, New York actually in one of the World Trade. World Trade number three building. This is our temporary office as we wait and get excited for our more semi permanent home.

 

Christian McCarrick  [0:59]

Oh, awesome. Excellent. And where are you moving into? You have a spot picked out everything? Yeah.

 

Scott Carleton  [1:03]

I’m really loving the reinvention of the financial districts, pretty much when they were rebuilding all these World Trade Center buildings. They were thinking, hey, okay, bankers and traders are going to come back in. But what’s been happening is Spotify is moved down here, Casper, we’re now going to be taking a floor and World Trade three. And it’s just an exciting, whole new reinvention of a part of New York. That’s always been traditionally financial focused.

 

Christian McCarrick  [1:30]

Pretty much right suit and tie pinstripe suit and ties. Right. I grew up in New York. Very familiar, especially back when I did that was the only thing down there.

 

Scott Carleton  [1:38]

Absolutely. My dad as well. So it’s nice to like, come back to his old work haunt and hood.

 

Christian McCarrick  [1:44]

Absolutely. Excellent. So Scott, for my listeners, you just give us a little bit of a brief background of sort of how you got to be where you are today, a little bit of that journey of Scott.

 

Scott Carleton  [1:54]

Sure. My journey. I mean, it’s kind of an unconventional, I started as a mechanical engineer. And I really did not want to code. I very much want to build things with my hands, find my own solutions, and learning about a link to lyst just didn’t feel directly applicable.

 

Christian McCarrick  [2:13]

But they’re so awesome.

 

Scott Carleton  [2:15]

Yeah, I’m come full circle. And I actually like love thing about algorithmic runtime now is like for fun, but that’s a totally different curiosity. Now, when I started as a mechanical engineering, I went into nuclear power. And I was just fascinated about like, oh, my god, there’s this amazing, like, greatest technology since fire. What is this vision doing? And we’re going to, like create systems to contain it. In the practice, I was writing Fortran, I was writing Fortran to do analysis of pipe analysis and fracture mechanics to kind of like, analyze every which way how a pipe might like fatigue over time. And although is fascinating, I was writing Fortran with several other mechanical engineers and didn’t have the slightest clue as to a good software practice. So when I started moonlighting at a web development, startup Coding and Ruby, I was, I was smitten because I was like, This is so elegant and beautiful. And you get to like, put a payment form right in front of a customer. And it’s really just between you two, like there’s no bureaucracy or anything like I’m providing value to a customer, they are accepting it or not, is very pure to me. So that got me hooked. I then built my own company hired engineers, I’ll get back to that later, my first management experiences. And from then on, went on to build more and more engineering and then technology teams. Most recently, before Asana, I was at a company called Mandela, whose mission is talent is evenly distributed, but opportunity is not. And the way they’re attacking that problem is to build out the software learning campuses, across Africa and Nigeria, and Kenya, Ghana and Egypt in Uganda. And so my software, I was essentially a remote CTO my software teams or over in Africa. And I would be building out platforms to empower anyone to have a self directed learning path. From there. I’m now joined Asana, and I’m the site lead of the New York office, which is kind of a engineering General Manager, where I’m both accountable for the success of the office, but primarily focused on engineering.

 

Christian McCarrick  [4:22]

Great. I always ask my guests, how did you get into being a manager? It sounds like your initial manager might have been from an entrepreneurial path?

 

Scott Carleton  [4:31]

Oh, yes, absolutely.

 

Christian McCarrick  [4:32]

And how did you get into that? Like, you just said, Hey, I’m starting something, and then hey, I need to hire people. And boom, you’re you kind of you’re managing them?

 

Scott Carleton  [4:40]

Yeah, I mean, I think there’s some in reflection, you know, like, years after the fact, I think there are some perverse incentives that can happen in early stage startups, that may have led to us hiring earlier than we needed or looking, you know, every problem like you want to use a hammer against. And so like, we wanted to scale up technology to attack those problems.

 

Christian McCarrick  [4:59]

Sure.

 

Scott Carleton  [5:00]

So like the moment we raise money, I was like, Okay, I need to hire engineers, we need to scale out all of these features that we need to build in order to have that time achieve product market fit. And, you know, perverse incentives, or not, or like hiring for the right reason or not, I got a really wonderful introduction to management. Because once I accepted that, I have no idea how to do this. I’m just going to go about it the way I think it’s right. My leadership qualities, and my my style of management got to be very emergent of the current problems I was witnessing, and also very, based on a discovery process of who I am and how I think people should be treated. So yeah, with like the first four engineers, like, we didn’t have enough capital to really pay new grads coming out of MIT. But I ended up getting fascinated with educating, you know, very hungry, smart individuals who just wanted to learn and come in and code and return for that passion, like, would work really hard, and we’d be able to figure it out together.

 

Christian McCarrick  [6:04]

And along that way, we myself included everyone, we’ve we’ve made some mistakes, these poor people, these poor souls that we managed early on, I always sort of, I apologize to them now, many years. But any any mistakes you made, or anything that you realize now in retrospect that you probably should have focused on done differently.

 

Scott Carleton  [6:25]

Yeah. Oh, man. I mean, I think I completely screwed up my first two hires. My first hire actually was a for operations. We were an art startup dealing and physical art, and I had to move it around. So I thought of like one of the smartest people I knew back in college, got him to quit his job and moved to New York. And three months, I had to fire him.

 

Christian McCarrick  [6:44]

Tough, yeah.

 

Scott Carleton  [6:46]

Yeah. And thankfully, we’re still friends. He’s a very kind and generous person. So he understood. But it was the first moment where a couple of things I learned like, it’s a lot easier to hire and manage. If you’ve done the job, yourself. And so you get that empathy, you understand where they’re coming from, you can direct their question and be either a mentor or coach, depending on the situation, but also describe and clarify the expectations. So then they can have the autonomy to know what they’re working in. My second hire was very much like, Okay, I need this great engineer, I’m going to hire someone out of Berkeley, who was passionate about the arts and like, really, super creative. I was like, Yes, this is the person. And I think for the next three months, I expected him to ask me questions. So I don’t think I really filled him in on anything. And so and that was a time in the company where we weren’t using chat systems or anything. It was really my co-founder and I talking about things as we like, left the office and came back. And we didn’t realize how much we were isolating our employees until one day he just like inventing frustration was like, saw me talking to a friend, like in our office and was like, you’re telling him more about the company, then thing you’re telling me the aspects of transparency and just like, context sharing and understanding like, Hey, we all need to be aligned on a common goal and feel like we’re working towards it together. Really kind of hit me like it was a kick in the shins? Oh, I just didn’t realize. So I agree with you like I, I apologize to all my early managees or team members, because of the drastic mistakes I made back then.

 

Christian McCarrick  [8:20]

And that’s an interesting point that you bring up I think, a lot of people, they don’t set out to be anti-transparent, right? I mean, it’s not like they’re purposely trying to hide things, or obviously gate or keep things from people. But in actuality, it’s just, they didn’t have the training, you don’t realize, or in one of the things I’ve learned over years to its, you can even if you say something once that’s not enough, right, you have to say it again and again, and write it down and say it again. And, and so I think we talked about transparency, you can put it on a lot of values. And a lot of companies have that as values. But unless you’re actually actively working on being that much, you know, implementing transparency is probably gonna fall short.

 

Scott Carleton  [8:57]

Completely agree, I think it’s become an hour. More of a sixth sense for me, I’m always looking for where’s the transparency does it exist? Like where does it not exist or where could be improved? We have a great value at a Asana that tends to be applied of like maximized clarity. And then on an individual basis for mentorship and coaching, we talked about like, are you creating transparency? Where I really connected as I’ve worked with distributed teams a lot. And when you are in a distributed setting, and mainly thinking like via your chat interface or task system, you kind of need a sixth sense of what has this person seen so far? Can you put yourself in their shoes of like, what might their world look like? And what is not transparent to them, and what might be opaque. So with that, I now think I think this is the root cause of also like managing expectations upward or side or down like crucial management skills, but also individual contributor skills that everyone can benefit from of keeping track of trying to read or ask other people like what what can you see, what can you not see, and continue to work to create more and more transparency, so that we can all collaborate?

 

Christian McCarrick  [10:07]

Awesome, great points in that. And we’ll get into some more of those in some detail to I think, the remote teams and managing that a little bit later in the show. Since you are lead, you’ve led teams VP, then VP of tech site lead, CTO, what are interesting for you, because you’ve probably managed managers at this point. Now, what do you do tips you have for new managers making that transition? Or if you’re coaching someone today, and then they’re going to level up to new manager, what are one of the top things, one of the top things that you you let them know, or try to teach them about?

 

Scott Carleton  [10:39]

I feel like there’s two parts of transitioning into management that are really critical there for every engineer, going from a here’s how I create value by a code and features just switching into the management context of – Well, how do I create value? There is a complete almost 180 on the feedback loop for success and give a high performing learner the right feedback loop and they’ll figure it out for themselves. But figuring out that feedback loop is really hard for new managers. The two things I would give to someone transitioning in is – create as much clarity as possible, on the the end goal of what you your team is trying to seek and make sure everybody understands that. This is something that actually comes really easy at Asana and I’ll explain about that in a minute. But most companies I’ve been at when you’re in the mix of different communication technologies. A good litmus test is asking everyone on the team like, what is the purpose of what we’re building? And why? Like, how does it serve our overall goals or serve the company, and a managers job is to make sure everyone has a ready answer to that. Now, the other side of actually having a feedback loop, which for a manager, they can understand how they’re being successful is whenever they’re working through all the minor issues that are going to come up and trying to achieve that goal of true alignment. The team is our people walking away from you like energetic and excited about the next task they’re going to take on? And have you aligned that vector of the company a little bit closer? Have we reached a little bit more clarity and understanding about what we’re doing? And why? And do we have a greater chance of doing it effectively? And if you’re just holed into those two issues, I feel like that’s like 80% of the job. And everything else is definitely important. There’s management is a never ending craft that you can continue to get better at. But I try to focus on those two big rocks with new managers. It’s like just starting on that, that clarity and looking for those small feedback loops to know if you’re improving at creating that clarity.

 

Scott  [12:45]

Yeah, great. Those are some very good tips and observations to talk about, and to let your new managers know about. I think, you know, one of the things that we want to talk about on this show a little bit too with you, Scott, is you’ve been involved in as you mentioned, previous the number of if not fully distributed teams, at least teams that were fairly distributed, including potentially Asana today, where you know, it’s a satellite office and your previous company, where you were one in one location independent, a lot of your team was in another and also on, you know, how do you are growing teams, right? What’s How can we help grow our team members? Right. So I think the first thing I want to ask and we touched upon it a little bit previously, is you’re the site lead for Asana in New York City, right. So you mentioned it briefly. But what does that entail? Like what is what is kind of a day to day look like for you?

 

Scott Carleton  [13:36]

I think as site lead I, as we define it in our Asana as areas of responsibility system, which is it’s our system to better balance out titles on the org chart, where we describe more of our responsibilities and what our goals are, and allow more fluidity in those changing responsibilities. So as its defined there site lead, owns the white space of the office, everything that’s not defined within the New York, geography rests on my shoulders for me to define or delegate or find it find a home for. But more so when I was looking at this role coming in. And from my past experiences, I kind of think of it as like, three C’s, if you will, one being context, how can I provide as much context as possible for everyone working in the New York office, how they fit into the larger Asana mission, the larger Asana company, and really connect all the dots across? So can I be the primary API between New York and the rest of the company, and internally, align that as well as possible? The inverse of that I think of as kind of clarity over using a term I apologize, but clarity for the rest of the company of what’s happening in New York. What What is New York need? What do I need to advocate for? How do I best set it up for success and get the resources maybe understanding or or just brokering and mediating process between New York and the rest of the company? So I’m also the main point of contact there. And then the third C is community like how does Asana and Asana New York specifically interoperate with the New York environment? This includes hiring, but really kind of the whole cycle from cultural events to integrate into the New York scene and, and how we represent ourselves here. That’s how I think about the meta role of site lead, as opposed to engineering manager, which is another hat I wear. And I’ve been surprised at how much tends to fall into those three buckets every time.

 

Christian McCarrick  [15:36]

Sure. It’s interesting, because I think my previous company was purchased by a bit of a larger company. And I ended up having a similar role. It wasn’t titled that way. But I was the most senior person in our San Francisco office at that point, right. So it became almost at the facto site lead. So it’s kind of interesting talking about that, because I’m nodding my head as you’re speaking not that no one can see it, but it’s kind going along. Yeah, I totally kind of get what you’re talking about there. Now, what’s kind of the size, what’s your New York office versus I think you’re headquartered in in San Francisco in the Bay Area?

 

Scott Carleton  [16:10]

Yeah, we actually don’t like to use the term headquarters, which I really appreciate. So we’re about 450 total employees now. And we plan on growing to 700 this year. So it’s a very high growth, high headcount growth year. And as Dustin likes our CEO, likes to put it, it’s very possible within the next few years that the total count of employees outside of San Francisco will be larger than San Francisco. So there’s, there’s no need to use the headquarters terminology. I came into New York last year at about eight people in the New York office, who had done some pretty amazing feature launches, including our boards and timeline feature last year, which is now the most successful feature to date at Asana. And now we’re hitting 30, might be upwards of mid 50s, by the end of the year, which is faster growth than Asana is typically used to and it’ll probably slow down after that, because we really care about ironing out culture bugs and stabilizing a lot of our processes.

 

Christian McCarrick  [17:05]

Absolutely. And one of the things you mentioned to and I want to touch on this, you talked about maintaining, you should have, you know, New York office and that culture, being from New York and another tech scene, there is totally different from, say, the Bay Area. One, how do you balance that we are part of the larger Asana team, right, along with, hey, we also have our own sort of unique culture. But we don’t want it to drift too far and want to still, you know, be part of the Asana family. How do you kind of balance all that?

 

Scott Carleton  [17:32]

I’m glad you asked this question, because it really racked my brain for quite a while because it’s a very tough problem. I mean, as humans, we naturally want to divide and put things in dichotomies, we want to have two groups and like, the worst behavior we have is thinking about us and them. And this is just what always seems to happen in separate offices like, Andela really taught me a lot about this while we were at Andela the Nigeria office was scaling hard, and Shani, who has been running the offices just a really, really amazing leader. And Kenya was also growing. And we kind of saw that although Adela had these core values that are acronym of like epic excellence, passion, integrity, and collaboration, I believe the flavor and all the different regions was like, really, really different each area. So I really liked our approach back there. And I’ve actually mimicked it at Asana, where it’s kind of a more of recording and reconciliation. So you really don’t want to stop culture from evolving, like, you don’t want to like hold it back. But you really do want to make sure some core tenants stay core and universal. So back in Adela, we had an Andela council or we were just kind of bringing the office leadership together and like compare and contrast notes and think about ways to like, what should be cross pollinated across offices, like what is successful, if you think about culture as aligns preferences that we believe will help us succeed, and then what things like should we start carving, I’m like, don’t fit in? Now, at Asana, we, the culture in San Francisco was like, very deep and embedded, because I mean, it’s evolved constantly as well. But like, that office has nine years of history. Whereas New York is quite a bit newer. So I wanted to make sure I really understood their respected that existing culture, because a lot of why I joined this company is so much of that I want to bring to New York, a lot of even a lot of Bay Area product development thinking I want to I want to bring to New York. Quick aside, I just love this quote from a friend of mine who’s worked on both coasts, where he says, the valley is obsessed with creating value and New York is obsessed with capturing value. And I feel like that that describes it really well. And so I want to bring more of that creating a value to New York. In order to attack this us and them problem, while still maintaining the freedom to have different expressions locally of culture and to encourage that evolution – I started by really looking for the cultural ambassadors of, if you will, Asana and recording the different cultural elements and how they linked to our values, and then how we actually reinforce them in a day to day practice. So that we could make that kind of an explicit way of working. And then kind of working with the New York team to check in on like, hey, like, do we all believe in this? Do we agree on this is this what we think will make us successful? And now once we have that out of the way, let’s start defining about how we will extend what’s possible for Asana and we think of ourselves as a triangle. And Asana often does because we talk about our pyramid of clarity. New York isn’t a separate triangle, New York is is a triangle within the greater triangle and trying to extend the base essentially, extend the impact surface area. And as we think about trying to remove that us and them mentality and more think we are a branch that will kind of like look to collaborate effortlessly with the greater Asana as part of our mission, while also extending what’s possible for it. And that’s the part where we have our self expression, and we can still be who we are, bring our whole selves to work be New Yorkers, not the not be west coasters, but still check in with those, those more universal values that we know, have left us success in the past will help us be successful in the future.

 

Christian McCarrick  [21:23]

Yeah, absolutely. And, you know, I think it’s an important topic to bring up because, you know, although, you know, Auth0 is, is predominantly distributed, but I think a lot of companies are, even if they’re not going to go necessarily completely distributed satellite offices, you might you might be in the Bay Area, you might be looking in New York, you might be looking at Austin, or Denver or something else. So I think the concept of more and more teams that are going to be working collaboratively that are remote, it’s just it’s just increasing year over year. Right?

 

Scott Carleton  [21:49]

Absolutely.

 

Christian McCarrick  [21:50]

So how do we avoid that us versus them is on a lot of my managers minds as well in the different places and the different locations we have. So, you know, interesting, I was just reading about Asana too, especially for you. So kudos to you and your team named 2019 Best Places to Work by Built in New York. So you know, good luck with that. But in your mind, what makes the best place to work? Like, what are the things that go into that? And if you were to kind of talk to other engineering leaders, and other people trying to create that, you know, what are the things that you can tell my listeners to do that can help you create a, quote, unquote, Best Place to Work?

 

Scott Carleton  [22:27]

Sure, absolutely. I mean, I joined Asana for for that reason, and more so like, I think, I tend to think in loops like virtuous and vicious cycles. Asana’s incentives are incredibly aligned to create the best culture. Like if you think of it as like, the culture is the tale that that wags the dog of our product. And like, at the very end of the, that proverbial dog is our customers paying for that product. And what they really want is like a better way of working at the seed of that we have to live and breathe and think, have a better way of working so that we can productize that and sell that we have a market imperative to deliver on that, which I think you could say, it’s easier for us to accomplish that than other companies. And I really want to deeply learn what that looks like, so that I can apply for the rest of my life. And the most important takeaway here, I’m going to borrow from Patrick Lencioni but his book, “The Advantage” really covers this. And I really like it, because it It fits the view, from my own experience. And that is, there’s organizational health and then there’s organizational intelligence, and that intelligence, all tech companies has smart people making good decision like they that can make good decisions that can like there’s no way you can discount that other companies don’t have smart people. And I’m sure they have the data. I’m sure they’re like they’re doing their best. But not all companies have healthy organizations. And the premise is that organizational health allows companies to get a lot smarter. So what is organizational health? That is the simple things like morale, but like politics, confusion, you know, these things that are just kind of in the water. Now, how do we combat those? The way Asana really thinks about this, and our mindfulness value is the impetus. But the application is a lot of reflection, and learning and building on the foundations from before and taking the time to think about what happened, do a five why’s make sure we’re like getting clear, actionable data, and very much incorporating that into how we work along with a lot of clarity of what we’re doing and why one of our missions and the product or not even a North Star, but something we’re achieving today. But we want to get it stronger and stronger and stronger is that any task an engineer is working on, they should be able to trace that task all the way up through their team’s projects through like the program that they’re in to the fiscal year objectives to the overall master strategy all the way up to the mission so that that engineer should know how that task is affecting the overall mission. And with that, that provides so much relief because creative foreignness is really important if ordinances of like, should we be doing this, maybe we should be doing it like it much more rational reason decision making. And I think that is the crux of organizational health, not having canceled projects, not having just the confusion, or like political jockeying, if we can, a big part of making collaboration happen is like that, we’re looking at the same set of data. If we’re looking at the same set of data, we can make reason and rational decision making. I think morale really rests on, do we think the game is rigged. If we believe in how the process in which decision got made, rational people will be okay with the decision itself. And then just making sure we build on top of that and strengthen it over time, is really the key to success in this arena.

 

Christian McCarrick  [25:59]

Next, and you pointed out two books, and they’re both by the same author. One is “Five Dysfunctions of a Team,” which I think has been recommended before. So I also do recommend that, but you also mentioned “The Advantage.” I don’t think it’s ever been recommended on my show yet. But in retrospect, it certainly should have we we’ve all at the SLT level at Auth0 have also read The Advantage. And you know, we really believe strongly in a lot of the things that it says so I’ll put those in the show notes as well, the two definite recommendations that I had that I will definitely agree with you for that.

 

Scott Carleton  [26:29]

Yeah, I’m a big believer in it.

 

Christian McCarrick  [26:31]

Now, I think the other thing important for teams and great work environments is helping to grow your employees like that could be career advancement, it could be professional personal development, what are the things that you do to help your managers help with their employees? And to help your individual contributors? What are some of the important things that you do that really feel to help contribute to that advancement for your employees and that leveling up?

 

Scott Carleton  [26:55]

At Andela, I learned a really important lesson, we were both a learning environment in a software environment. What’s great about say, SAS, or MVP culture, and the lean startup is getting feedback from your customers as early as possible with like, is this valuable? And then you focus your work on what will be most leverage to work for that customer, which means you’re always like, working on leveraged opportunities. And they’re not. It’s not the same as like learning for your own joy or benefit these growth opportunities when like, yeah, I could go read a textbook on like, digital signal processing. But if I don’t have an application of it, like, Am I really actually growing? So what I’m getting at here, and what I think the importance is for managers is thinking about the allocation of growth opportunities to what the business actually needs. So what I saw at Adela is we would always have this problem of incentives where a developer might say, well, I need to, I need to level up on JavaScript or become an expert in Android, so that I can say you can get better projects and get better pay. But the reality is, like, if that wasn’t actual leverage work, if it wasn’t useful, then they weren’t really learning the skills they need to learn. So I think this is true at any company. And especially, it’s important Asana or anywhere else, where I work with my managers to say, let’s always make sure we’re aware of where our people want to grow, and where their zone of genius might be lying, like what is particularly that they’re adept at where they want to learn it, and have that as like, one list. Then let’s work on processing, what are possible opportunities to help us achieve our goal is to help us achieve our mission? Those are really truly leverage opportunities that we can match with our people. And only when those are like, allocated effectively, do we really get true growth for our people, and also the business succeeds. And that is like a true Win Win partnership that is very, very sustainable. If a manager is acquiescing to a reports, demands for like growth opportunities, and that is not providing leverage value for the organization, it will actually be a vicious cycle and not a virtuous one. However, when we have leveraged opportunities that do align, even though it’s not perfectly with the stated desire of growth from a individual engineer, it will be close enough. And it will be up to that individual to glean from it what kind of growth they want, and then to and they will be that much better for it. So I emphasize with my managers, and also when I’m dealing with my own individual contributor reports, that the kind of opportunities I will be presenting, the impact of them are important to the business it is needed. And I can frame it and put the paradigm as this is what I know about you, this is what I know that you want to learn and how you want to grow. And this is where you want to be in five years, or like, when you leave the company, I know you want to do this, this is how you can get that out of this particular opportunity. And it will be all the better for both of us, and also very sustainable. And we can create a wonderful flywheel of these opportunities where you continue to grow.

 

Scott  [30:04]

Yeah, and that brings back to the point you mentioned earlier about context. And if your employees have as much context as possible, as much clarity as possible, you know, they are going to help themselves in a bit because they’ll know what’s going to help the business as well. And they can also help align themselves to bring things forward that will help them in the business. Right. So that’s a win win as well.

 

Scott Carleton  [30:24]

Absolutely. Something I think a lot about is the skill of problem identification. And if they have access to all that information, and then they can start raising problems and saying this needs to be attacked or like the next step, not even asking permission and just like going for it. Now we’re much more than the sum of our parts, like where that’s true support as management and not like a top down directives.

 

Christian McCarrick  [30:47]

Sure. How do you recommend engineering managers sort of stand out from all the other engineering managers out there? And a lot of people just get promoted – and they probably shouldn’t. And so how do you rise above the crowd and be that really top engineer manager?

 

Scott Carleton  [31:01]

I think the most important thing for manager or IC, but definitely for a manager is to reframe and reset the expectations of where of the kind of feedback you want to receive. So in any given relationship, it’s very easy for me to have a relationship with a manager of mine, who I am evaluating as, say, entry level manager covering this team or these people. And this in my mind is what I expect of them. And therefore I will be giving them feedback along that reference line, that often will not be broken until some paradigm shifts or that manager themselves – states – Hey, like, I want to be a lot more of that. Please give me feedback along the lines of if I’m would be managing multiple teams. Or if you expect a 50% more from me on performance, how how would your feedback change that? Because often, I think our feedback will be coming to a person that their current level and not where they want to be. That’s a incredible indicator of a growth mindset of I want to be a lot better than I am now. I know I won’t be there tomorrow, like I want to understand the growth to get there. But please put me on that path. And please, like, hold me to that standard. So another thing that I think will also make a standout manager will be the direct opposite of asking for help saying, Hey, I am overloaded. I think this area is really hard right now, how do I get help appropriately? To achieve this, I think the best managers, especially when you really index on the people side, unless the technical side are really upfront with their vulnerabilities and challenges and know how to find other people or ask for help to, to handle them. And this is advice I can give over a podcast. And I can say that I still really suck at this. Personally, like it’s one of those things as a manager where I start to realize I’m giving advice that I’m not taking it, but I know is exactly what I should be doing. So I’m now looking for ways to steadily long term focus of like building over time, reminding myself of my own challenges and vulnerabilities, writing to myself every day of like how I need to forgive myself for these vulnerabilities, ask for help and actually get it because that will have a much bigger net impact to the organization than if I like just try it lone wolf it and grow alone.

 

Christian McCarrick  [33:22]

Yeah, no, absolutely, definitely. Great points. One thing and you’ve talked about this a couple of times, and I’m asking you this, because you’ve worked in a number of distributed teams, and you brought it up, I think in an article that was written to let’s talk about Slack, you’ve used Slack before. And as teams grow and it becomes part of your sort of DNA in your backbone of communication, but how do you wrangle and manage the slack overload that tends to happen? I know you talked about it, your previous company to public channels, and it just suddenly you lose things you can find them they any tips you have, because I know a lot of my listeners too are heavily involved in Slack and and sometimes it can be overwhelming.

 

Scott Carleton  [34:02]

I love Slack. I’m so glad I came out. I was using HipChat before. And I just appreciate it much better design and also a way of distributing this technology to a much wider group of people than we had with IRC. That said, I think we’re asking way too much of that tool. If email is like a stack last in first out, then slack is a log. And it’s a really, really great place to hash out some some information. But like it’s, it’s just a log like, no one really enjoys querying a log to like, pull up key information. What I really love about Asana is like, it is a graph that you can constantly be indexing and organizing. And a lot of Asana is actually have all their email forward into a sauna because they can organize it more effectively. And I’m very glad to say at Asana, most people don’t use email unless they’re external facing, they just use Asana and our Slack is still pretty critical. But it’s not stress inducing, I get no anxiety for having missed a message on Slack. So yeah, my previous writings and thinking was like, how do we use this tool effectively? And I thought like, well, we need to force public channels, we need to bite the bullet and like, say more things in rooms of 100 people and ask questions and have that vulnerability, but build a culture with that’s, that’s okay. And then also take the most relevant, important information and get it out of there to be collaborated on and like Trello or something. And now my current reflection is like no that we’re just asking too much, it’s too hard to change those kind of behaviors, especially with a tool that’s that flexible. So I would say for, especially the tech organizations that are always looking for better productivity uses – stop asking too much of it. It’s going to be much harder to change people’s behavior there and they’ll be much more effective to think about, what are the kind of problems do we need to solve? What are the kind of decisions we need to make? Even before tooling, like how do we want to do that? We can do it in a more manual way. But like what’s going on understand that workflow, let’s get it into a tool that will actually accommodate that workflow, and make it really clear and allows to build on top of it. Slack, I think will have diminishing returns if it’s the only system for making decisions.

 

Christian McCarrick  [36:15]

Yeah. No, great, a lot of us muse about it, what’s the best solution? And obviously, you work for a company that has some other solutions that are also complimentary as well.

 

Scott Carleton  [36:25]

We’re not going to fight against the weight. It’s just different areas.

 

Christian McCarrick  [36:28]

Great. And you know, one thing a lot of engineering managers, they stress out about, like taking a week off, right? Or a long weekend even sometimes, right? And I know you recently took some time off, you know, I think for family reasons or mental health reasons or whatever, it’s such an important thing to do to be able to take a time off and and we don’t always prioritize in tech companies. So how would you recommend managers prepare, you know, to take time off, whether it’s for a well needed holiday, sabbatical paternity and maternity leave any tips you have for being able to set yourself up for success, your team’s up for success when you’re gone?

 

Scott Carleton  [37:02]

I took six weeks off for a paternity leave. Asana actually offers 16 weeks, and I’ll be taking more of it later this year, which is a really exciting and like, it actually is very much built into our ethos of long term sustainability. And like you will be a better more engaged employee if like you have this time with your newborn. And I agree, it’s like a very special time. And the reason I didn’t want to take longer at first was I mean, his office was quickly growing, I was going to be asking a lot of other managers to cover for me. Here’s how I structured it is a month out, I changed my username in Asana and Slack and was like, I’m going to be on paternity in four weeks like and I would counter down each week. So everyone was super aware when they were assigning me something and what’s going on. And then I create a thorough a project of Scott’s paternity leave projects and Asana covering all of my responsibility areas, not as specific responsibility, but they clear areas and describing here is going to be the only of it. Here’s the backstop for that if you need to go to someone else. That’s all kind of like the setup of who’s going to be covering and where should people go. So at least directing people into a faster path. I think the more important part, once you have that covered is you kind of theorize what’s going to go wrong, like what are the things that really could go wrong with with your absence? And a lot of that I made sure to grab one on ones, with stakeholders of different teams and get their idea of what would go wrong. And a lot of it would be kind of the breakdown of the role I described at the beginning of the podcast, like the context, clarity and community. And as I thought about that, and I stack ranked, okay, what things could really fall off this list. And can I choose one or two, that if those things fell off, they would be bad. And then I created some, here’s some possible areas that I know I would be handling here. And if they go wrong, and then I just made sure a show that to the team and other managers like this might not happen. But this is like how I could project it going off the rails. But I also fully believe in your ability to handle this. And I just want you to know, however you do handle it. Fantastic, will learn from it.

 

Christian McCarrick  [39:16]

Great. It’s so important. And I think it offers a good opportunity for you to look at some other people in your team that can you can delegate more to they can step up, especially if they’re looking to increase some of their responsibility and looking to have their career growth themselves. I think it also can lead to good, good opportunities as well.

 

Scott Carleton  [39:33]

Yeah, I’d like to add another point on that, as I always remember, I think Derek Servers had this post ages ago, he was describing himself as that like fanatical founder and his team finally telling like he just need to leave for a while. He went to like Japan for like two months and came back and was blown away at how well everyone was doing. And at Asana, we actually have sabbatical every three years, where people take take six weeks, and it’s now that the company is around nine years old. It’s it’s almost as a wonderful cadence of people giving up responsibility. And then being able to come back refreshed. Look at the the work and the org a new and be like, Where do I want to apply my impact? So it’s, it’s almost this really healthy, almost biological system of like, giving up and then re-breathing life into different areas.

 

Christian McCarrick  [40:22]

Yeah, that’s an awesome, sort of part of the culture that that you have there and Asana. So it sounds like very well justified earning those words, you have Best Places to Work and everything. So it’s awesome. Thanks for sharing that. One thing I ask all of my guests on the show, any good books, resources, something you found read recently seen recently that you kind of want to share with the audience here today?

 

Scott Carleton  [40:45]

Yeah, I still think Seven Habits of Highly Effective People is like a really terrific book. I spent a lot of time going deep on what are my principles? What are my values? What is a mission statement for myself? And I have now I found incredible power in rereading that each week and reflecting on my week and thinking like, Am I getting closer or Am I being the person who I want to be every day? I think that big switch that that book helped me with, and a few others, but it was if you’re if you’re always thinking about what you want to be, you’re always going to like, be pretty distant from it. But if you think about who you want to be, you can try and achieve that every day. That was a big switch for me. The other one I think is pretty terrific is a it’s kind of like the the central piece of culture at Asana. And I think it’s particularly good, which is the conscious leadership group. The book, I think it’s called the 15 commitments of conscious leadership. It kind of builds on a lot of the seven habits, ideas, I don’t think it’s particularly unique, but the the way it was delivering it, I was very receptive to and resonated a lot.

 

Christian McCarrick  [41:50]

Excellent. And, Scott, if any of my listeners out there want to reach out to you, maybe they want to work at Asana or they just want to kind of jam on some of these ideas we’ve talked about here, what’s the best way for them to get in contact with you?

 

Scott Carleton  [42:02]

You can follow me on twitter at Scott or see Scott ERC. And my email is Scott at Asana. happy to hear from you.

 

Christian McCarrick  [42:10]

Well, perfect. Well, Scott, I know you’re busy. And I really appreciate the time to have this conversation with me today. Really enjoyed it. Thank you very much.

 

Scott Carleton  [42:19]

All right. Thank you, Christian.

 

Christian McCarrick  [42:20]

Thank you for listening to this episode of the Simple Leadership podcast hosted by me, Christian McCarrick. If you’ve enjoyed the show, please subscribe. And don’t forget to leave a review on iTunes. Full show notes and additional information can be found on simpleleadership.io. If you know someone who would be a great guest for the show, well, you want to share your own experiences please drop me a line. We’ll see you back next week for more technology leadership tips and advice as I interview more top software engineering leaders.

 

Christian McCarrick  

 

This is simple leadership. Welcome.

 

Thank you to our sponsor Policy Room for helping make the internet a safer place by offering identity as a service and supporting this podcast.

 

We’re here to learn from new and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams. Do you want more engineering management leadership tactics and information? Subscribe at simple leadership.io to receive the latest updates from this podcast. Hi, I’m your host Christian McCarrick. This is the SimpleLeadership podcast. Welcome back. Today’s guest is Bryan Helmick. Bryan is the co-founder and CTO at Zapier, a workflow automation tool that connects all Bryan the apps you love and automates repetitive processes. Since the company was founded in 2011, Zapier is scaled to 200 employees and more than 19 countries supports over 1,400 app integrations and empowers millions of customers. Bryan worked in product development for Veterans United or he built products focused on bringing Veterans United to veterans on social media. He holds a degree in finance from the University of Missouri, Columbia. On today’s episode, we discuss growing and scaling remote teams, including the unique challenges of hiring, onboarding, culture, and employee mental health. Good morning, Bryan, welcome to the show. Thank you excited to be here. Awesome. And where are you calling in from today, Bryan?

 

Bryan Helmig  

I’m in Mountain View. So here on the west coast.

 

Christian McCarrick  

Oh, excellent. I’m over in the East Bay of San Francisco. So we’re, you know, pretty close. So this time of day, it’s probably a bit longer than then in the middle of the day with traffic and whatnot. Right. So as I asked all my guests, Bryan, little background, you know, how did you get to where you are today? Kind of the highlights of what you’re doing?

 

Bryan Helmig  

Yeah, so the bulk of my working life has been at Zapier, which does a lot of automation for SAS apps. But my background kind of took a little bit of a path through certainly not a quite technical background, def had the financial sort of schooling, kind of business background and university and starting just tons of I don’t know if you can call them startups. They’re like small, like little businesses that were enough to pay for like beer and stuff like that, sure. But started like dozens of those little things and learned a lot and worked at kind of a mirroring of finance and tech, there was a company in Columbia, Missouri, which is around where I grew up, that did VA mortgage loans, which were VA backed loans mortgages. All their sales motions, everything was done online, which was kind of novel a little bit. This was during like the “Great Recession,” right, where one of the few things that was still like alive and growing was the internet based mortgage loans that were also backed by the Federal government. So it was kind of a weird lucky spot to kind of be that was like just growing through this giant downturn. And that’s where I learned just a ton about tech and about like marketing and about how to build some of these sales motions for different kind of segments, even more specialized segments. So that was kind of the foundation of what got me into Zapier eventually, for that.

 

Christian McCarrick  

Sure. And now, give me a little bit of overview of Zapier, like just a highlights how long you’ve been around. What is the pitch for the company?

 

Bryan Helmig  

Yeah, we’ve been around, it’s crazy to say it’s like slow little over seven and a half years now. And Zapier is a way to make yourself more productive at work, generally. The way you do this is through automation, you can hook up triggers and actions, and when you get a new row and a spreadsheet, you know, look up something else in the different spreadsheet and then send a text message, or add them to email marketing list or when someone fills out a form on your website, whether that’s a type form or gravity form, or Whoo hoo, add that to your CRM, you can add little rules and pieces of logic in there. So it just really helps you move data between services and build like automation, which you would traditionally need to hire an engineer, right? Like an engineer to build this out and fire up your API’s and hosted somewhere and maintain it and pay them bunch of money to do that, and now with like something like Zapier, you know, for less than $50 a month, you can kind of create these little robots that run around your business and do a bunch of stuff for you. So that’s kind of Zapier in a nutshell.

 

Christian McCarrick  

Yeah, awesome. And to all my listeners, there’s like one zap that I use that makes my life bearable dealing with Slack today, you know, so I shout out for that I use on a daily basis awesome tool. I know a number of people at all, also use different pieces of Zapier and there’s apps so your company makes my life easier and better. So it doesn’t get much more better than that. Right?

 

Bryan Helmig  

Yeah, we say Zapier makes you happier. That’s our mnemonic.

 

Christian McCarrick  

Excellent. It helps you pronounce your name. Yeah. Now, Zapier is interesting because you were part of YC? Is that correct?

 

Bryan Helmig  

Yeah, we went through the summer of Y Combinator, which is when we moved, I mean, I had mentioned we were in Columbia, Missouri. That’s where way Mike and I had met, we got into YC. And we just moved out to the west coast that summer. So that was the summer of 2012.

 

Christian McCarrick  

Interesting. So you’re one of the co-founders of the company, and the CTO, the company, any major mistakes that you’ve made running teams, especially kind of you came in to Zapier, you’re probably didn’t have a ton of management experience and that’s kind of common for a lot of people who are starting and running their own startups. But anything that you look back and say, Wow, yeah, I could have done that. Or I might have done that differently.

 

Bryan Helmig  

Yeah, I mean, I feel like often the common thing, I remember hearing this advice from folks that were running startups before, like when we went through YC, I heard it so often, that it almost became wallpaper, but it was like actually ended up being just utterly foundational is just how important hiring is. You hear it all the time. And I almost feel like you hear it so much. Yeah, like I said, it kind of turns into wallpaper a bit. But when you live it, and you maybe make a couple hiring calls that you regret, or you have to like work on or you have to fix, it becomes very real. And it makes like your life so much easier when you surround yourself with really, really talented folks. So as I look back on any of the mistakes that hurt the most or spent the most time on fixing or whatever, I feel like they all come back to people and the quality of people that you hire, how you handle situations around feedback and performance. And how you work through those, those stick in my mind more so than I don’t know, like a technical decision you made that you had to roll back or, you know, some of those things, they seem pretty significant at the time, but they just kind of fade away. But the ones that really I just looked back in like, man, we could have done a better job there. I feel like they’re all people hiring, coaching, handling that sort of situation feel like they all come back to that.

 

Christian McCarrick  

I agree to I think as I’ve gone through my career in different companies to even coming up as a technologist, it sort of evolved into coming that you know, the people after you can get that, and you really take care of that the other things just sort of happen, right? I mean, you you hire the smart people you trust, you take care of them, you put the right processes in place, right? And then you can really enable them to build whatever you really need them to build, right and product value.

 

Bryan Helmig  

Yeah, absolutely. It’s kind of like inexplicably kind of it doesn’t happen automatically. So it’s not that far, but it like it feels closer to that then it does on like great hiring is not automatic. But if you get great people, and you kind of give them direction, and the very, like even high level direction of this customer has this kind of a problem. That’s usually enough for really solid folks that just like dig right in and do some amazing stuff. So that feels more automatic. The thing that’s not is the hiring side of stuff like that, you have to be really, really thoughtful and careful about and that kind of goes back to I just remember hearing everybody say that so many times that it just started floating past me. And it didn’t hit me with like, the magnitude of which it mattered to some of the other things that felt more, I don’t know, more immediate, right? Like, especially in those early stages, those things feel more immediate, you’re trying to like fix bugs that are blocking customers from upgrading, and you’re trying to maybe you’re trying to close like an investment round or whatever, like all those feel so like, you know, do or die kind of a feeling that you know, those longer term things just get neglected. And that’s the one longer term thing that if I could like pick a time machine back like that would be like or write a letter to myself, I guess like that would be that would be top of the stationary.

 

Christian McCarrick  

Sure. So for all my listeners out there anyone thinking about starting companies, you know, advice here from Bryan is hiring, you may hear it a lot. But it absolutely is so important. And I agree. And we’re going to talk about hiring a little bit and specifically hiring and remote companies and remote teams a little bit later in the show. So I want to make sure we get into that too. Now speaking of hiring, you started off small, you’ve grown, I looked at your website to your hiring for engineering managers now, what are you looking for in engineering managers at your company, especially for remote managers, right, especially if they’re coming to first time managers, any tips you have or things that you specifically look for, for people now they’re going to be running your teams?

 

Bryan Helmig  

One of the things we found is really well correlated with success in a remote organization, some sort of background, communicating in an asynchronous manner is like a default mode. And the way I would describe this is classically, in places where you’re maybe more of a consulting relationship or a client based relationship, that doesn’t need to be the predominant background. Infact, it’s really great to have more product focused experience, longer term, product focused experience, that’s really important. But sometimes just having that default mode of, I wanted to communicate with a client, I had to write a really thoughtful email, or well articulated email or get my thoughts across in that manner, or over a call, or something that’s not in person as the default mode is really, really important. So we often look for stuff like that, in the absence of Oh, I’ve just done remote before in the past, which of course is like kind of a gimme, that’s a big one. When it comes to management, we also think of places that have, if it’s a mixed environment, I think that’s always like pretty informative, because in a mixed environment where you have some folks who are remote, and some folks who aren’t, those sort of structures can kind of get a little bit leaky and messy, especially if you have cases where let’s say management is local, and some of the workers are remote. And how’s that managed. And those sorts of reflections on that are really, really important to us. So we really want to dig into those if someone’s like, Oh, I was in a mixed sort of remote local environment, we always like dig into that. Because those, that person is generally going to have a lot of nuance, and like thoughts around what works well in one or the other. And how does that mixed culture sort of work. It makes them think at a higher level at that. So we often ask about that sort of stuff. Those are all big things that we like, look forward for managing, I mean, beyond the classic stuff of, Hey, we care that engineering managers were engineers and their past life, it doesn’t mean that they need to be the greatest engineer right now, that is not the goal. But to have empathy for engineers and be like, yeah, that’s a tricky problem. I know, that’s a tricky problem, I trust you on that is really, really important. So we look for things of that nature, as well, along with just the lifecycle comfortable, being comfortable with the lifecycle of employee recruiting, interviewing, performance, coaching, letting folks go, like if you’ve seen all that stuff, maybe you experienced it firsthand, you’re probably going to be a pretty seasoned manager.

 

Christian McCarrick  

Perfect, thanks for that. And given your experiences as a CTO and a fully remote company, I want to spend the majority the rest of the show also discussing growing and scaling remote teams, I think it’s one thing to start them right? And then it’s a completely other thing to how we grow them up from 20, 30, 50, 100, 200 people

 

and there’s a lot of inflection points along the way. And to kind of want to get into some of those, for myself, personally, also passionate about this Remote VP of Engineering myself, I sit remote, like I’m at my house right now leading the distributed team. So and I think, you know, I want to point that out. It’s, as you mentioned, not everyone at Auth0 is remote, but I would say about 85% of our engineers are. And I thought it was very important. As you mentioned the leadership, right for me, I’m not sitting in the in the central office, and the rest of my team is remote. And I’m actually eating the dog food. And I think to your point about empathy that goes a really long way for your teams.

 

Bryan Helmig  

Yeah, 100%. And I think that line between managers and our executives, to just the folks who are traditional, like I see, having a mix there is really, really important. I feel like you get these local and remote sort of things, or at least I’ve heard certainly, I’ve heard from folks that we’ve talked to that whenever conversations just happen automatically, locally, you just lose so much of that awareness at some of these really key conversations, they just kind of exist in one realm rather than the other. And I think there’s companies that do it really well, I’m sure, there’s probably thought put into it for Auth0. I mean, 85%, being remote is a huge portion. I know, Fog Creek used to do something similar, where it was like everybody had if you’re going to do a call, even if one person was dialing in, everybody walked to a different room, right and would hop on the video call. And the those sorts of fundamentals are really really key, like holding a culture together, whenever it’s space across remote in, in person.

 

Christian McCarrick  

Absolutely. And I can go into a whole nother episode about the the mixes and how to do that. But it’s a very interesting conversation, ah, You know, feel free to reach out – to anyone wants to DM me to talk about that I’d be happy to. Now, I was going through a number of the things that are on your site, and one of the things you had talked about three ingredients to running a successful remote company and you talk about team, tools, and process. Now, do you want to spend a moment a little bit talking about kind of the team, you talked about a couple things like doers and other things and kind of go through some of the thought process that was behind those three items that you singled out?

 

Bryan Helmig  

Yeah, 100%. So for team and it’s kind of comes back to hiring, we tried to really make our values more behavioral, more real, less poster values, right? “Be excellent,” you know, as like a value doesn’t feel often actionable. Our first value, for example, is “Default to action.” We’d rather people just kind of make a call and an educated guess, obviously, but move forward, especially in a remote environment, that’s really important where the person who has the definitive answer is not going to be awake for another six hours, you can’t just like hang up your keyboard, and you have to kind of move forward and you had to be comfortable with that. So that’s something that you can ask in an interview, when it comes that. Tell me about a time where you sought forgiveness rather than permission, right? Like, that is another way to frame so that stuff. And you can kind of really dive into some of the behaviors there. And I think that’s really key when you’re talking about a team that can work in a remote environment, super important. So that’s number one. Tools, was the second one. I mean, this is back to values. Again, one of our values is, “Don’t be a robot, build the robot,” which is obviously very aligned with our mission as a company. But the tools themselves kind of drive, how your organization works. Of course, we use things like GitHub and Slack and all those amazing tools for working and those are the space you work in, it’s your office, right? A lot of people even with true physical offices still have that as their office. So you’re kind of working remote already. But you’re just kind of doing it with this extra physical 3D space as well. But we look at things like there’s all these robots running around Zapier, all these zapps that are doing all kinds of stuff at all hours of the day, automating all kinds of different things. So it always feels like Zapier is like humming, like the sun never sets sort of on Zapier because we have people everywhere. But we also have bots doing all kinds of stuff all the time. And that’s just a part of our culture. And that comes back to tools that enable that. And then you look at things like process. We’ve had to change process, and I’m sure you guys too, like just as you grow, things that work before just don’t work anymore, they just fall apart. And we have to be able to revisit those pretty regularly. Not be really dictatorial about the process, but still try to have some consistency. And we try to do this through interfaces. So a classic interfaces deadlines, like just let us know when this thing is going to get shipped. And if it’s not, we want another interface to be some sort of feedback so that we know that this is changing. That’s something that can stay fundamental. It doesn’t matter if you do Scrum or Cod Bon or which tool you use or whatever. But you should let other people know when you’re going to deliver on something. And if you’re not, you should let them know what’s changing and why. And that is the sort of primitives that we’re looking at when we look at team, tools, and process and how those kind of flow together.

 

Christian McCarrick  

Yeah, they’re all good points. That’s excellent, too. Now I do want to run into go into something we started talking about. And we’ve kept coming back to already in this conversation, hiring. So important for any company, right? Whether you’re remote or co-located or whatever, now, Zapier, 100% distributed, what have you found are the benefits of being able to hire from a fully distributed company.

 

Bryan Helmig  

I think the biggest benefit, by far is the quality of folks you have, you are now able to pull from anyone in the world, if you have a Core Python contributor that lives in Johannesburg, you can hire them, like, as long as your culture can support it, you can hire anyone, you’re not bound by geographic radius of within 30 kilometers, you know, 10 miles or whatever you have that is limited by a commute an hour or two of the day, just like eaten up by this time. So in and of itself, not only is it just a great like lifestyle thing, but it also helps you hire the best people as a result. So for us, we’re able to pull in these really great folks, I get so excited whenever there’s an amazing engineer, that’s I don’t know, in a small town in Ohio, like, that’s really exciting to me, versus there’s obviously amazing engineers in the Bay Area. But it’s so cool, that opportunity can be spread out. I mean, we believe that that that maximum that talent is kind of everywhere, but opportunities not. And we feel like we can kind of invert that a little bit and actually provide opportunity a little more widely and get great people who are everywhere haven’t had a chance to maybe work in an environment like ours, and we can pull them in and make them really successful. And that’s I don’t know, that just that’s really exciting. And when it works, it feels really good.

 

Christian McCarrick  

Yeah. And we found, at least myself personally too that, it really I think helps to offer opportunities to say other groups and some underrepresented groups that might not have the opportunity to live in the Bay Area, or have grown up or be able to afford it or have another job here.

 

Bryan Helmig  

100%. And you see this, like you see this diversity in culture, you see this diversity, and language and experiences that is worldwide rather than American centric, or a US centric, which is in itself, like, certainly I’m not a monculturalist, that’s not what I’m getting at. It’s just, it still has that kind of Western view on stuff. And if you can pull in other viewpoints and other perspectives, it has tons of even business, like if you’re going to try to spread, do internationalisation or go into different markets and you have people who live and breathe and they’re like, it just feels so much more natural. So it’s it’s not just like a moral good. It’s also a great thing for business as well. It just makes you more present in the places that you want to be as well. So it’s just great all the way around. We’ve seen it, it seems like you guys have seen it as well. So we’re kind of like preaching to the choir here.

 

We found it important.

 

Christian McCarrick  

Something that we struggle with a little bit too. And this is a question that comes up a lot is around timezone and timezone preferences, especially around teams and working together. What is you know, Zapier’s view on time zones you hire specifically for time zone instead of geographic region or, you know, how do you handle that?

 

Bryan Helmig  

It’s definitely a consideration. We’ve come up with different processes that help manage time zones, but we haven’t cracked the case, I guess, or cracked the nut for that. There are places where time zones work in your favor, you can take advantage of them. A classic example is infrastructure on call carrying a pager, you should just do it during your normal hours. And that’s that’s a really nice quality of life thing. Carrying a pager, and waking up at 3am is never fun. Like, no one’s ever excited to do that. Yeah. So the fact that you have someone who’s just like, “Hey, I got this, you know, I’m awake, like this is just part of my day” is a benefit, right? That’s something that’s great. When it comes to folks on teams, like within a team, I don’t know how you guys do it. But we try to, we try to really make sure that everybody has, you know, one or two hours on a team. And maybe this has two or three front end engineers two or three backend engineers, a designer data and the PM. Maybe those people all have one or two hours that they do have together. And we find that that works pretty well. The default mode for most, let’s say engineers, is to be heads down and like building stuff, right? Maybe not all your time, but a good chunk of your time. So actually having a little bit of timezone diversity there so that you could go a little bit deeper, well, things are a little bit quieter, can be a positive thing, too. So for us, we’ve just tried to find ways to sort of manage it and use it to our advantage where we can, you can’t do it everywhere. But in the places you can, we found it to be pretty effective.

 

Christian McCarrick  

Yeah, I agree with that. I think a minimum of you know, because you do have to get some people together, whether it’s for a stand up or sprint planning or retro, like it does help to have some time where everyone can get that quote unquote, Zoom face time, right? Too to get that now, lots of positives. What are some of the biggest challenges that you’ve seen with having the such a distributed team and hiring specifically?

 

Bryan Helmig  

I think some of the challenges are probably not a whole lot different from kind of a physical location. But I think you hit them sooner, right? So especially for us, I know that we had to formalize the way we communicate a lot sooner in the lifecycle of Zapier. I’m not sure how your experience played out. But it seems like for us if we didn’t like lay out what some of our expectations were, it was easy to kind of get a little bit lost. a specific example is whenever new engineers are brought into Zapier, like, the advice I often give them is you’re going to feel like you’re a pest. And that could not be further from the truth of like the reality of this. If you don’t ask like a dozen or two dozen questions a day on Slack, you’re not asking enough questions like that’s the default failure mode, for folks in a remote environment is they are too quiet or they think they’re being annoying, or there’s just this thing about chatting on Slack or something that can kind of feel that way. Whereas maybe if you’re in a co-located place, and you look over and you see someone like scratching their head, or kind of visibly frustrated, or you can kind of like, Hey, what’s going on kind of a thing, and that feels more natural. But somehow it it doesn’t feel as natural, bringing that to purely digital. So you have to work at that. We had to had things like that brought into our culture and the way we communicate, that just help grease the wheels there. A classic one as well is we’ve tried to train people on when they need to raise the bandwidth, I think the classic thing you hear is you have a big thread in Slack. It’s like 100 messages. It’s like, Okay, it’s time to just raise the bandwidth, hop on a Zoom call and hash this out, right? Those are just some of the things they seem a little bit funny, they seem a little bit obvious, in hindsight, but you have to lay that out. And you have to be specific about that in a remote environment. Otherwise, people just kind of keep defaulting to those behaviors, and they may not be the most optimal behaviors. That’s something that we found. And we see a little bit of success and trying to kind of formulate that communication pattern.

 

Christian McCarrick  

I definitely was chuckling when you said that because you see that behavior of the, you know, the hundred Slack channels and everything, the threads, you’re going insane. And it’s hard to even keep up. And then sometimes you notice that the threads of that on each other over right with 12 hour window when someone started waking up and then participating in right. So yeah, I like that kind of knowing when and codifying so as a good expectation of when it’s time to jump on that higher bandwidth, like get on a call again, on a Zoom. I think that’s, that’s a good point for all the people out there.

 

Bryan Helmig  

Definitely, we also so have people, when you do hop on a Zoom, we try to have folks recap and summarize when they get back, like when they wrap it up. And just try to say, Hey, this is what we kind of decided, so that folks don’t miss out on that. Or we record a lot of stuff and upload them to things like Wisteria. And then we often recommend people like us like the there’s some Chrome thing that you can extension that lets you like speed up your videos. And then we have lots of people talking and chipmunk voices at like at two or three x. So that’s really helpful to get context if you want to. And it keeps people engaged no matter kind of where you are in the time zone spectrum.

 

Christian McCarrick  

Absolutely, yeah. We do a ton of recording too. But it’s like anything, the speed up things. Interesting thing. I’ll have to take that tip back too. Now, one thing I want to I want to get to right is how do you optimize for remote interviews and getting the proper signal? This is something I deal with in our company deals with every single day. How has Zapier sort of optimized for getting that remote signal properly?

 

Bryan Helmig  

Well, I think a lot of its stuff that is is not unique to remote. It’s things like having a consistent rubric, having consistent questions, trying to compare apples to apples as best as you can. We do stuff like take homes, we think that kind of matches the reality of the work. It’s not perfect. We’re constantly grass is greener on the other side sort of thing when it comes to hiring processes. So some of that stuff, I think is kind of table stakes. You know, some of the things that are unique to remote? Are you emphasize a bit more. Again, the default mode of communication. How did they come across in their emails? What was their internet quality like? Did they find a quiet spot to get on the call? Were they in a loud like coffee shop and you could barely hear them? Or were they distracted on the call? Clear like messing around with something, those sorts of things matter more, right? Like they matter a lot more in a remote environment. So those things are things that you would think of that are I think unique to remote. When you think of the default modes, how you going to communicate with this person day to day, how did they come across in those mediums? How much effort do they put in those? That matters a lot. But beyond that, I feel like a lot of the standard hiring things still hold right? Be able to have consistent interviewers try to treat people fairly, all that stuff is still top of mind as well.

 

Christian McCarrick  

So I want to talk about something I know that your company does. And we do at Auth0 and it’s polarizing a little bit. And I know you have to take homes and we have an exercise. We have people who love it. And they think it was really they enjoyed it. They enjoyed interacting with the teams first. And then I go on Twitter, and I have people that are saying, well, you’re getting free work and your exploitation and you’re paying them. How do you feel about that? How do you handle some of that, if you’ve seen that on your side?

 

Bryan Helmig  

We’ve gone back and forth. We’ve done live whiteboarding ones we’ve done, take homes, and I don’t think there’s one perfect solution to this stuff. We’ve done stuff where we’ve kind of allow people to choose your own adventure sort of thing. And then you get issues with not being fair and comparing people. So it’s a really, it’s a really hard thing. Anytime you’re trying to judge another human’s skills or whatever, you’re only getting a tiny snapshot, it is very lossy, we just kind of have to acknowledge that it’s imperfect, really from top to bottom right, like just going to be very, very difficult. So if you start from there, you’re just really choosing at least I feel like you’re kind of choosing from the lesser of two evils here. We found that a take home test lets people work in a more natural environment with what the work will be. I just don’t see people hopping on calls and whiteboarding their code on a daily basis. And if you excel at doing that, I can understand why you’d want that in your interview process. But that’s not how we work on a day to day basis. So it would be disingenuous to present it as such, and I don’t think it like measures what we care about. So we do have a portion after the take home, where we try to recap a little bit of how they approach the problem. And a lot of times you actually get more signal from this, I often tell people that are interviewing that sometimes it’s what you don’t decide to add to the take home and your reasoning for it, that might put you over the top. So if you say well, I could have done X, Y, and Z but because of the time reasons I decided not to. But here’s what I would have gotten out of it as a result and be able to talk in depth, because that tells me you’re able to make trade offs, that’s really important. So these sorts of things can be like really instructive, not just on the take home, but also in how you review it and how you have a conversation about it afterwards. We definitely don’t have people work on the product or do like a week of work ahead of time. We did try that before. And we tried paying people for that, like, Hey, take a week, we’ll pay you and just kind of work with us. And we found that that was highly disruptive too. I mean if you got a family or you already got like a job, it was a big ask, it was really big ask for folks. And we found that that just didn’t work either. So some people liked it, some people didn’t. I think it’s really hard. And it’s, it can’t please everyone all the time, right? It’s really difficult. You just do the best you can and you just recognize that it’s kind of imperfect, but you keep working on it.

 

Christian McCarrick  

You made a good point, I think though, is making sure that the work and the type of work and the situation you’re going to be in matches what you’re actually going to be doing on your job. It’s like a sort of going into a an engineering position or developer position where all you’re going to be doing is crud work. And you know, you’re doing red black trees on board, right, it’s just it’s not quite exactly the work you’re going to do. And for us, we want to optimize for asynchronous because that’s the majority of the work that we do.

 

Bryan Helmig  

Right. And the thing I often ask is, especially when we were reviewing because we review and try to have a consistent rubric and like intro and project, like read me and everything. The things we asked, What’s the narrative for how this is applicable to Zapier. So if you have a question about database design, how is that going to matter to them? If they’re on the front end, you’re gonna have to spend a pretty good yarn. But maybe if they’re on the back end, and they’re talking about distributed Well, you know, if you looking at range keys, and how you query that across, like a shard, it matters. Oh, okay, I buy that. I think that’s a valid question as a result. So I think your point of like, could you design a red black tree is just kind of like signaling between engineers that know that kind of deep information. And maybe it’s not trivia, you could get to trivia like, you know, tell me about this particular API and the jelly it’s like, that’s not, again, not important. So those things, we try to really curb, just like straight out and just get back to the meat, like, what’s the first project you’re going to put them on? Think of it through that lens? Like, are they going to build a component or higher order component and react? Okay, maybe that’s the thing that you should be asking about. That’s more fruitful conversation to have then, like you said, red black tree. And then you come in and you build rest API’s? You know?

 

Christian McCarrick  

Yeah, exactly. So after hiring, you made an offer, candidate starts. How do you as a remote team, or remote company? What are the things that you do from an onboarding process at Zapier and has it changed at all as you’ve scaled?

 

Bryan Helmig  

Oh, it’s changed a lot. We used to do a thing where we would get everyone every month, we would have all the new folks fly out to California, we’d meet them. And that was fun. That was really great. We enjoyed that. But we also thought maybe not perfectly aligned with wanting to run a fully remote company. So we thought maybe we could try doing remote onboarding. And the first two weeks, we have really structured so we kind of follow this graduated autonomy style thing where the first week you have almost no free time, right? The second week, you have a little more free time. And maybe you’re spending a little more time with your manager, talking more about team stuff. That first week was fully company immersion, learning about like the history of the context of stuff we’re working on that second week. A little less of that third week, you’re almost all over to your manager at that point, maybe a little bit of lingering stuff, you need to like wrap up, we use things like Lesson Lee and a couple different courses. So you could like work through this stuff at your own pace. And then by that fourth week, you’re diving into a project, you’re building all that stuff. And we try to do this in a very like graduated autonomy style thing where we’re just very structured, to more loose to more, you’re guiding yourself, you’re kind of handling this stuff. Always within obviously a framework, you’re going to land on a team, you’re going to have specific work you want to work on there, we try to get engineers to writing their first bit of code as fast as possible, we try to get support folks to answer their first ticket as soon as possible. And we try to make it really easy, just so you learn the motions, right? You should learn the emotions of the job before in the environment before you have to really apply brainpower to the problem, it just reduces the number of things that could go wrong. I often tell people, the best thing you can do as an engineer on your, you know, first week is ship a typo fix, right? Because like, it can’t mess it up, right? There’s no, there’s no confusion about am I doing this, right? You’re learning everything about the motion of how things get into production. That’s like the best thing. And then yeah, add in about face, then move on to working with someone else on a feature, then owning your feature, kind of, again, graduated autonomy at that point. So those are the ways that we approach onboarding. And it’s gotten better, I think, as we’ve gotten more structured, and more thoughtful about this, we do a lot of internal surveys of new folks. And, you know, existing folks, and the scores say that people are pretty pleased with the direction of it. So it seems like the more support you give people in those early days, the better they do, and the faster they feel like they’re, I don’t know, like, they feel like they’ve been around for a while because they’ve got extra context. And they kind of know where everything’s, everything’s at.

 

Christian McCarrick  

Sure. That’s great that structure, I think is really important to there’s some other information on your, on your website too that. And I want to bring that up for a second. If you’re a remote manager, or you are a remote worker, go to kinda Zapier.com, I’ll post them stuff in the show notes, there’s a lot of good material around working, remote working, they published something called, “The Remote Work Survival Guide,” I think just all good tips. A lot of the stuff you get is like, change out of your pajamas and you know, set boundaries and like that’s it. And there’s 100’s of those articles. Right? Yeah, but I think your team certainly has put out some great content. So you know, thanks for doing that helps the community so appreciate that.

 

Bryan Helmig  

Yep, we’ve put a lot of thought into it. We create a lot of these things internally. And it just feels like it’s not that difficult to clean them up and share them more widely. And we’re big believers in this, it sounds like you guys do a ton of remote and are big believers there as well. There’s just not a lot of examples out there that do remote, well, there’s a few and they’re starting to pop up more and more. But I mean, I just feel like this is kind of the way the world’s going to work in the future. There’s no real reason why we all need to be co-located in one spot or the other when we have this medium by which we’re working through already, like a turn when even when you’re in a physical location, like you’re chatting over Slack if your code lives in GitHub. So it’s inevitable. I feel like that’s the way the world is going to work and another decade or two.

 

Christian McCarrick  

I mean, that brings up a good point that there aren’t a ton of companies. But there’s more companies starting and the companies that have been in existence, yours is one of them are starting to grow to some level of scale now. And there’s even much less information about that, right? So I mean, companies that are greater than 100 people remote. I mean, I can talk to you maybe Envision, I think is Buffer there. I think at this point, some of those companies, Automatic is certainly one that’s sort of one of the pioneers of that, but are any things that as you’ve grown and scaled? There’s a lot of stuff in your website and different things. What are the biggest things that you have had to say change, specifically from being a remote organization over the time as you scale that just don’t scale as well anymore? I mean, off sites, retreats, anything like that?

 

Bryan Helmig  

Yeah. I mean, the onboarding thing was one that I think was changing. That’s a big one. It’s funny, you say this, because I’ve always thought there was a big dearth of information of around even just growing an org from 50 to 250, something like that. There’s a lot of people telling you about how to start a company from scratch, lean startup kind of thing. So there’s no shortage of that. And then there’s a lot of people writing kind of, you know, retrospectives of or memoirs of like, their giant corporation that they, right, but in the middle of Coke, right, exactly, or Apple or whatever, right? Like, okay, neither one of those are really useful when you’re in this middle area. And it kind of feels like a no man’s land. I wish there was more if people have great recommendations, like, I’d love to hear about them. It just seems like there’s not a lot of information out there for this, especially for high growth companies. So the things that we’ve saw, if I had a number one thing is like a takeaway is that change is the only constant, if you can embrace the idea that the thing that you slave over and like sweat over. And finally, land on a solution that you’re happy with. It’s going to break in another six months and be useless. If you can get comfortable with that you kind of have a zen like approach to handle this, because there’s no, it’s maybe a bit paradoxical. There’s no like one solution size fits all. But the one thing that I’ve never heard is like, Oh, yeah, nothing’s changed for us as we grew really fast. So just getting comfortable with that, you’ll probably be ahead of the pack, because you won’t hold on to things that just don’t work anymore, that are broken. A lot of the things that we did wrong, as I look back, probably fall in that camp of just holding on to something that wasn’t working anymore, whether that’s someone in the org that wasn’t really feeling their position anymore, or, you know, a process that kind of broke, or maybe even something really, particularly like a technical choice that no longer was working, but we were banned dating, it’s still and like, all these things. They’re all in that flavor of Yeah, things are changing. We’re not addressing the change as fast as we need to be, or we’re not as comfortable addressing the changes we ought to be. I feel like that’s kind of the fundamental thing. But above that there’s like a million, there’s like a million cases of it.

 

Christian McCarrick  

Yeah, no, the changing is so important. And even when I talk with rolling out different things to my teams, and I talked to other peers and other companies, people get that emotional or whatever safety attachment to things. And it’s much better to be proactive, if you can, right, you don’t want to be so much premature optimization that you’re scaling for things going to happen 18 months in the future. But if you can get a little bit ahead of the curve, I think with seeing the wall that you’re going to hit and maybe making some slight changes, right before you hit it, I mean, perfect, because once you have to deal with it, and retro, like you said, it’s a lot messier,

 

Bryan Helmig  

Definitely a lot messier. I mean, it’s kind of like the old maxim, like, if you don’t like the weather, just wait a day, it’ll change kind of a thing. Often, that’s how startups sort of feel, right? So you’re not happy with how the process is working, like given a month or two in, it’s gonna probably be a new process. So just being more comfortable with like, hey, everything’s an experiment, everything’s going to change, it makes sense to think a little bit ahead and try to get maybe an extra month or two out of something, but don’t obsess over it either. So there’s, there’s a very Zen balance to it. And just kind of like working the problem sort of thing is kind of at the heart of it. But yeah, it turns to tricky one.

 

Christian McCarrick  

One thing I do like to talk about, and not just with remote employees, something you know, that every manager and every leader needs to be more aware of, I think it’s employee mental health. And I think the challenge in with remote employees makes it even harder. What are some of the things that your leaders and you coach your leaders to kind of be on the lookout for specifically, and tips on how to do that with remote employees?

 

Bryan Helmig  

Yeah, it’s great question, we try to talk about it a little bit, we have rooms where we can like talk and dive into some of this stuff as well, just being open about it can kind of be helpful that, hey, you’re not alone and feeling maybe a little isolated, or a little lonely when it comes to a remote environment. And of course, this is people different, everybody’s different. So some people are like, thank God, I don’t have to interact with people, right? Like, thank you. And other people, like I could use a little more interaction. Everyone’s different. So there’s no one size fits all, either here, you know, some of the advice we often give folks is, if you have a habit and your past roles of using work as kind of your social structure, that is going to be more difficult at Zapier, or a remote organization. It’s going to be a bit harder to do, it’s not impossible, but it is going to be harder to do. So you’ll want to set aside some time to touch base with friends or local friends or whatever. Like if you’re the person that kind of needs that stuff. Or maybe it’s family, maybe, you know, friends that you have that are local, that might be what you have to lean into a little more. Those are just little technical things that are going to be top of mind. For folks who who kind of need something like that. When it comes to a more remote environment that has how are people communicating how are people handling, it’s easy to read into. The example I often give is like if someone just says like, response to you write up a big thing, like with a passionate thoughts and like really articulated and they respond with like “K,” you know what I mean? Like, it can kind of feel dismissive, or maybe you misread some signals or whatever, like that can sting more right? In a remote environment, because you miss out on the physical cues, right? Maybe that person was just like, in the middle of a call. Maybe they’re in the middle of a podcast, right? And they’re in they couldn’t like respond, but they wanted to acknowledge you, right? So it’s often useful to take a step back and say, Hey, what did you mean by that? Are you are you not happy with that thought, or you’re not and get more clarity and seek that clarity is really important, can really help on that front, that’s often like a source of friction, that can directly impact sort of mental health, because it’s easy to ruminate on those sorts of interactions or feel rejected as a part of those interactions, when there may be totally valid reasons outside of that. So seeking that clarity, I think is something that can be really helpful for folks. I think remote has a lot of good stuff. But it also has a couple things just kind of keep in mind you have to like actively manage.

 

Christian McCarrick  

Yeah, you made a good point earlier to you can’t be lazy, and you can’t be lazy with documentation. You can’t be lazy with communication written or verbal. You can’t be lazy with management. So there’s a lot of things, I’d like to say that all the things that you should be doing even at you know a co-located office, right? Sometimes you can get away with not doing them all and be lazy, right? But you really can’t do that remote.

 

Bryan Helmig  

Lazy is not the word I would use. It’s just Lazia Fair or just kind of being like complacent a little bit with it. Like I said, especially when it comes to social cues and interactions. Humans are so finely attuned to that, right? And it’s easy to overemphasize them if you don’t have the rest of the context. And just being able to recognize that I think is like step one be like okay, I’m maybe I’m just misreading this, I don’t have enough context here, I’m just going to seek a bit more of it is like usually just stopped zero for some of this stuff. But it can be a little bit trickier. When you’re doing that.

 

Christian McCarrick  

One thing Bryan, I ask all of my guests on the show, if you have any recommendations for my listeners for resources on either leading engineering teams and or remote teams, anything you’ve read recently, or it stands out for you that you would recommend to my listeners?

 

Bryan Helmig  

It’s funny the podcasts that we really recommend managers specifically listen to. It’s funny when you listen to it. It’s like just so like, so straightforward and makes a lot of sense as the Manager Toolkit. Yes, it’s great. It’s just no nonsense, straightforward advice on this stuff, which I always I always recommend that for folks who even want to get into management. I think a lot of the stuff there holds and remote. Some of it doesn’t like I think there’s some funny stuff like awkward situations like how do you deal with body odor? and then

 

maybe doesn’t apply as much so you get to skip over some of those but a lot of them is still really, really hold. So I often recommend things like that. I really recommend if you’re into remote, there’s a lot of great I think 37 signals, wrote some stuff on remote. I think some of the early stuff there. Check out the companies Auth0 included like writing a the leaders there. Zapier as well get labs of the Automatic folks. Open Source I think has especially really well run open source organizations things like Elastic, Get Lab I guess is open source as well. Mozilla a big one, very remote forward. Think of how they approach that stuff can be very instructive.

 

Christian McCarrick  

Yeah. Excellent. And I’ll post some of those on the show notes as well on SimpleLeadership.io. I know that Zapier is hiring. So Bryan give me like the 90 second elevator pitch. Why should people work at Zapier?

 

Bryan Helmig  

At the core of Zapier, we try to automate stuff, and we try to help everyone automate everything that they do in a daily work life, predominantly. This is classically required people have tons of capital, right? Hire engineers and do all this like complicated work. But now you can just kind of string stuff together. It’s kind of giving engineering abilities to non engineers. I mean, you’ve seen like attempts at this through stuff like visual programming, things of that. But the way we’re kind of approaching it is like from just like, Well, what do you want to accomplish? And like, how do we really like bake in a great experience there. So we’re just trying to bring automation to more and more people are trying to make it a lot simpler to get started with Zapier, we’re trying to like get Zapier in front of more and more people. So everyone can kind of be their own engineer and work on all this stuff without being technically minded. If you can snap together a couple of Legos, you should be able to use Zapier and that’s really what we want. So if that excites you, if you think everyone should have that ability, that’s something that you should definitely chat with us at Zapier. We’re hiring, you can check us out Zapier.com/jobs tons of stuff up there. Like I said, we share a ton about how we work. So you can really kind of interview us before you interview us if you’d like. You can see how we do stuff.

 

Christian McCarrick  

Excellent. And they want to want to reach out to you, Bryan with any questions, what might be the best way to reach out to you?

 

Bryan Helmig  

Of course, all of our emails are on the website. So if you go to Zapier, our emails are up there, but you can hit me up on Twitter, I’m usually on there as well. Feel free to ping me. I’m always open like as you guys can. I love talking about Zapier, so I’ll never turn down an opportunity to nerd out on the subject. So

 

Christian McCarrick  

Excellent. Well, we’ve been speaking with Bryan from Zapier, and I really appreciate the time you took this morning. Really great conversation, and I’m sure my listeners will get a couple of great points out of it. Thank you. Thanks Christian. Thank you for listening to this episode of the SimplerLeadership podcast hosted by me, Christian McCarrick. If you’ve enjoyed the show, please subscribe. And don’t forget to leave a review on iTunes. Full show notes and additional information can be found on SimpleLeadership.io. If you know someone who would be a great guest for the show, or you want to share your own experiences, please drop me a line. We’ll see you back next week for more technology leadership tips and advice as I interview more top software engineering leaders.

 

Christian McCarrick  

This is simple leadership. Welcome.

 

We are here to learn from New and seasoned technology leaders who all share a passion for improving the craft of technology management. Let’s take a deep dive into management and leadership challenges and best practices specific to Software Engineering and Technology teams.

 

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Hi, I’m your host Christian McCarrick. This is the simple leadership podcast. Welcome back. Good afternoon or good morning, Melissa and Jonathan. There’s the two of you on the show today, which is super exciting. I kind of love making the format a little dynamic here. We have to have you on the show. So both of you, welcome.

 

Johnathan Nightingale  

Thank you.

 

Melissa Nightingale  

Thank you.

 

Christian McCarrick  

Absolutely.

 

So one of the things, and it’s pretty prescriptive in a lot of ways,  I just want to kind of Do a brief introduction to introduce you to the audience who’s listening on my show. So since there’s the two of you, just maybe a high level, brief  background, how the both of you got to where you are today, and then what you are doing today a little bit.

 

Johnathan Nightingale  

Sure. For my part, I went to school for cognitive science and artificial intelligence. But I did it a long time ago when AI wasn’t nearly as cool. And so when I got out of school, I started as a programmer at IBM, and I was not working on AI stuff. I was just working on business integration software. I did that for several years before finding out in 2006 that Mozilla was hiring and I was pretty excited about that. That was a big deal for me. 2006 was sort of a dark time for the internet. But Firefox was a bright light and the idea that I can work on Firefox was really exciting. So I quickly stepped up and started interviewing. I said, “You know, I think I’d be good for this job. But if it’s not this job, I’ll do any job you have because you’re building the future of the internet and I want in.”

 

I was at Mozilla for a long time. That’s where I met Melissa. In  variety of engineering roles but eventually as a Manager of engineering, the Director of engineering, finally a Vice President of Engineering and then I closed out my time at Mozilla, as the General Manager of Firefox – Firefox desktop Firefox for Android – and while I was there, we built out iOS as well. Then I left. Mozilla had gotten to be about 1200 people Firefox was half a billion monthly active users but there was also a big startup community in Toronto that I wanted to be a part of.  So I consulted there for a little while before taking a Chief Product officer role at a little company and helping them grow past their Series B. And then in 2017, Melissa and I quit our jobs to build Raw Signal Group, which is where we are today.

 

Christian McCarrick  

Awesome,

 

Melissa Nightingale  

Cool Christian, in terms of my background, I went to school and I majored in public communication and minor in computer information systems. This was in the 90s and I graduated in 2001. I knew that I wanted to work at the intersection of communications and marketing and technology and so I moved to Silicon Valley basically two weeks after graduating from my undergrad.

 

For those of your listeners who know their history, 2001 was a really idiotic time to move to the valley to go get a marketing job, right there were no marketing jobs in the valley at that time, everybody was handing out pink slips like, it was the dawn of ” pink slip parties.” Most of the money was drying up and it was sort of the height of the .com bust. But my computer information systems minor turned out to be really useful because while there weren’t marketing jobs, they certainly were still paying people in California to develop software. And so that’s where I started my career and spent about four years waiting out a bad economy and coding in a dark room for basically eight hours a day and then moved into a role as money started flowing back into the valley in 2004, I found opportunities to work at PR agencies sort of at the height of like the web 2.0 bubble right so a lot of the the hype cycles around how we talk about technology, were just beginning to take shape, and around 2007 found out similar to Jonathan that Mozilla was hiring for their very first PR hire, and was really excited about that opportunity.

 

I went and ran the PR team at Mozilla for a long time and then following a five year stint at Mozilla took a VP marketing role at a company called Edmodo, that was building k 12. ed tech software. And then following working at Edmodo moved across the country, basically to be closer to Jonathan, and took a role at a Toronto based startup called Wattpad that was really sort of growing here and growing both a Toronto presence but also a really global footprint in terms of their user base. And then in 2017, similar to Jonathan, left my startup exec role and founded Rossignol group.

 

Christian McCarrick  

Awesome. Well, I think that’s a great background for the both of you. And there’s a couple reasons why, I always like to ask sort of my guests about their background, and one of them is, there’s no great single path to get into – “What does success mean? What does Engineering Leadership mean?: And people come from all different backgrounds and I really want to make sure that if I have listeners who are thinking about getting into engineering leadership and management that again, no matter what your background is feel free, like we come from all backgrounds, and you can be successful, and even sometimes more successful from a non traditional background.

 

Melissa Nightingale  

I think one of the questions we get at Raw Signal Group a lot of the time is from leaders who are asking, like, “Can you do management training? Can you do leadership training just for my engineering leaders?” And for us, we feel like there’s a big breakthrough for many leaders when they realize that the management skill set is much more similar across disciplines than it is different across disciplines. We will hear from engineering leaders who feel like, “Okay, I really need to know sort of management and leadership fundamentals just for engineers” And for us, I think our experience is that there’s a lot more that those folks have in common with the folks who are trying to lead the sales teams within their organizations, that are trying to lead the marketing teams within their organizations, that are trying to sort of grow the customer success function within their organizations. That they share a lot of the same pain points, but often aren’t talking to each other because they assume that it’s very different.

 

Unknown Speaker  

Yeah,

 

Johnathan Nightingale  

Yeah, it’s sort of a beautiful thing in the room when we get a management team together. We’re working with like 100 person startup, they’ve probably got 18, maybe 21 people in their management group, and we’ll get them in and, it’s often the first time that different parts of the organization – I mean, 100 people, like you can know everybody’s name at 100 people, you can know what they worked on and when they were hired – but it’s the first time that they’ve really heard that, “Oh, sales is also struggling with like, how do I do career path thing when the organization is growing really quickly?” Or “Or how do I get my team aligned around the stuff that the business needs us to do even when it’s not the stuff that they’re most excited about? How do I balance skills development versus just keep your head down and get your work done?” All of those challenges really cut across and so we find it’s an eye opening moment for those folks.

 

Christian McCarrick  

Yeah, and that’s a great point for all my listeners as well to understand and we’ve discussed on some previous episodes in slight detail too that and it’s okay not to just get the information from that but as people look for – we talking about mentorship or coaching also look outside of just your engineering org for those people who might be maybe a little bit more advanced either in your org or outside of you org in other disciplines?

 

Johnathan Nightingale  

You’ve certainly had guests talk about this before on the pod that the transition from individual contributor to a manager , let’s say, in an engineering organization, it’s like starting a whole new job, right? We say this all the time that yes, your your engineering skill is going to give you some credibility, some ability to talk to your team, some ability to help mentor them in certain contexts, but it’s really a totally different job with a different set of skills and a different scorecard and different measures for success. And we’ll have a bunch of people who not along with all that, and so “Yes, totally, that’s what I’m feeling right now. That’s what I’m struggling with is it’s a whole new job.” And then we’ll turn around and say, Okay, great. And like that person over there, who’s a new marketing manager, it’s a brand new job for him or for her as well. Right? And they’re like, “Well, but engineering management is sort of different. It’s a different kind of thing, right? You’ve got to understand Scrum, you’ve got understand like estimates and delivery schedules and how to integrate with a roadmap.”

 

Sure and marketing’s different too and sales is different too and operations is different, too. But there’s a community of practice waiting to happen in your organization where the managers can talk about the thing that makes them the same, right? I mean, I’ve managed engineers for most of my career and front end engineering is very different from back end engineering. But those people still feel like they can talk to each other.

 

Melissa Nightingale  

Yeah, I think we have this sort of common expression that it’s lonely at the top. The higher you go, the fewer people around that you feel like you can relate to and talk to. And that’s really challenging. Leaders get themselves sort of into, they paint themselves into a corner where they feel like other leaders within the organization don’t understand their challenges and so the result is that they often do feel very lonely that they are carrying a lot of the organization’s stress on their shoulders without a place to sort of talk it through. We really do see a lot of leaders find relief in finding both those sort of peer relationships within industry. But those peer relationships across the org are so, so valuable.

 

Johnathan Nightingale  

Yeah, Christian will let you get a word in edgewise in a second, but it’s one of the things we hear all the time. Like we you know, we run this newsletter every couple weeks where we just talk about management leadership stuff. And one of the things that’s really fascinating is we get letters from people saying, “Wow, you’re really speaking to the problems that I’m facing in agriculture in Kentucky, right? You’re really like this, you singing my song when you’re talking about the issues with like, labor organizing in New York.” And we’re like, we didn’t say anything about that.

 

Unknown Speaker  

We’re talking about management and growing tech organizations, but it’s all made of people and the skills you need, there are at least 80% the same.

 

Christian McCarrick  

The thing too  to point out with one of the things Melissa said is, it’s getting help from other people. But I think sometimes as leaders and no matter what discipline you’re in, you look across, and you have this false sense of, “Oh, they know what they’re doing and I’m not and I don’t and maybe, maybe I’m a little embarrassed to go ask them something because they clearly know it. And I’m just floundering over here. ” When actually if you go and talk to them, they’re probably having the same struggles you are and it’s good to have that peer support network.

 

Melissa Nightingale  

We talk about the skills you want to steal, right? If somebody else has a skill within your organization that looks really compelling, or you feel like, “Gosh, I’d really like to know how to do that, or how do they approach that?” It is a vulnerable moment to be able to go over and say, “Hey, you’re doing this thing.”

 

But it’s also a really lovely moment between colleagues to say, “I see you doing this thing. And I’m curious, can you tell me more about it?” It really is sort of this pure play mentorship moment of, “You’re doing this thing with expertise. I want to know more about how you’re doing it”

 

Unknown Speaker  

And

 

Johnathan Nightingale  

I think the other thing I’d expand on there is that, Christian you’re talking about looking across the org at peers and feeling like they’ve got their shit together. This works up and down the tree too, we talk to a lot of founders and CEOs who are like, “Okay, that’s a great course for my managers but nobody ever taught me how to run a one on one, nobody ever taught me how to give good feedback. Like, where’s your program, we’re all the CEOs can talk about i?” Because they’re struggling often with the exact same stuff unless you work in a gigantic Corporation that’s got like an executive development program internally in a management development program internally. And unless it’s a good one, it’s very easy to go pretty deep into your career without  any of this background, I tell the story all the time that when I got promoted to be the VP of Firefox, I had, you know, hundreds of millions of monthly active users, I had 100 to 200 person team at that point. You know, I had a $300 million a year, P&L. And nobody had ever taught me how to run a meeting, right how to set goals really effectively, how to manage change in my organization and keep a diverse team well aligned. I maybe had some basics about interviewing, but not even about strategic hiring and comp conversations. You’re learning it all on the go, and I was trying as hard as I could, but, boy, you can teach people this stuff. These are learnable skills. You don’t have to guess at it.

 

Christian McCarrick  

Exactly. So that’s a very interesting segue. As I sort of mentioned to you in some of our pre podcast conversations, I like to do a lot of research on my different  guests that I have on. You have a lot of information out there. I totally internet stalked you, I think.

 

Unknown Speaker  

and learned a lot of good thing

 

Unknown Speaker  

x course.

 

Unknown Speaker  

Oh, I didn’t, I didn’t I didn’t find that.

 

Unknown Speaker  

There’s somewhere tucked into page eight, I was neither the fastest nor the slowest, but they are up there on the internet are very internet.

 

Christian McCarrick  

But part of the thing too, which is we’re kind of we’ve come along for the internet journey at similar times. and our paths are somewhat similar a lot of ways and I was reading this and I was like, “Wow, this is my tribe!” Like the both of you, I’ve been through a lot of the things I was nodding my head, I was appreciating some of your bluntness and some of the sarcastic humor you have. That’s why I mentioned well we could have a conversation for hours, you know, pour Scotch or something. But when at some point, did you look around and just really internally declare that leadership today, especially in technology was just completely FUBAR? Like, was there a realization? Was that something that grew and you over time, where like, “Holy shit, we can’t continue like this like, and we have to do something?”

 

Melissa Nightingale  

I think for both of us, we felt like 2016 things sort of came to a head, and I’ll let Jonathan speak for himself. But in terms of sort of my own experience, I felt like the longer I was in technology and managing people, the more I figured out that there was a big gap from the first time I was managing people to my first executive role in terms of education, in terms of preparation. And that was something that meant in a tech context where we talk so much about the value of speed and so much about the value of iteration that I spent a lot more time and a lot more cycles on things that were entirely learnable and where there were models from other industries that certainly could have been applicable and were applicable in a technology context. Like Yes, startup is different in a lot of ways. But there were things that that I felt like I learned the hard way in startup that probably did not have to be as painful as they were. And I think in 2016, particularly for me in terms of context of what was going on in the broader world, there was a lot of discussion happening around tech’s awfulness coming to light – and I think particularly Susan Fowler’s blog post was with a tipping point, and that was early 2017.

 

Johnathan Nightingale  

Yeah, I feel like the blog post from Susan Valley was interesting, because when I first read it, it’s disgusting to read the way she was treated and it was sort of like, I got to the bottom of like, “Yeah, that’s not surprising,. ” Right? And that first response that like, I work in this industry, where a person can write that and I can be like, yep. I’m not accepting it. I’m not excusing it or anything but when my first response is like, “I don’t doubt for a second that that’s true, because that is an unsurprising story from our industry.” I had that first reaction, but then I had this second reaction, which is like, “That’s bullshit. It can’t be that that’s a thing that we’re blasae about, that people feel unsafe at work, that they feel bullied and harassed at work, like, How can that be something that would just like oh, man, that was the brakes when you’re moving fast like and it unlocked a thing for me where Melissa and I have said this before that, when she was at Wattpad when I was at Hubba, we would build these teams and we had this mantra like, i”I’s not going to happen on my team, because I’m going to I’m going to train up my managers, right, I’m going to be clear with my people about what’s expected to them. I’m going to hold the line on cultures and values that it’s not gonna happen on my team.” And I just got to this point, and I think Melissa did too, where that was no longer satisfactory, where it wasn’t good enough to say, “Yeah, the industry is full of poison, but at least my little corner of it is okay.” I think there’s virtue in that I think if you’ve got listeners who are fighting that fight, that’s so important. I’m not taking anything away from it. But for me, I looked at it and said, we can do more her, we can have more of an impact and take that conversation out of two startups and into the industry in general, and that’s, that’s what drove a lot of our writing in the early days as I drove the book, and I think it’s what drove us building our company too.

 

Melissa Nightingale  

Yeah, we love technology. We are internet people, right? We love the web. We love technology and felt like, this is our industry and if our industry is a mess, and we want to stay in this industry, then we got to do something to clean it up.

 

Unknown Speaker  

Mm hmm. So you have

 

Christian McCarrick  

So you’re running your own consulting firm today and helping people do this. I usually ask people like, what are the major mistakes you’ve made? But I think in this case, I want to change it up a little bit and ask, you’ve been coaching and consulting new managers, CEOs for a while now – what are some of the things that you see  over and over, so the mistakes you see like the patterns of mistakes that you walk in?, and you’re just like, “I betcha, you know mistake, bingo, we’re going to see one, two and three.”And sure enough, you see them.

 

Melissa Nightingale  

Oh my God, so many.

 

Johnathan Nightingale  

Yeah, and not from a place of dunking on them, like I have a lot of sympathy for how hard it is when it’s going so fast and when nobody equipped you to cope with it. I do want leaders and executives even in fast growing organizations to take accountability for it and feel like it’s on you if this organization becomes poison. But I have sympathy for the fact that your org can grow faster than you do at first. And so we never go in to dunk on them or to score points off them. But the premise of your question is totally true. There are patterns.

 

Melissa Nightingale  

Yeah, I mean, in terms of common mistakes that we see at orgs, basically, of every size, but folks who are sort of new to it make this mistake more often, is the sort of expectation of mind reading. It’s, I have context around the organization, either because I founded the organization or I’m one of the early employees of the organization, and I expect that other people have that same context. Christian, I think you were flipping through the book, there’s a chapter in it called “Obvious to you is not the same as obvious.” It’s a mistake that we see startup leaders make really frequently is to assume that the things that are in their head that are really clear are in the heads of all the people working for them or with them, and it’s one that will bite you. If you can say it out loud you get so much farther, when you can sort of bring other people into the assumptions and you’re working assumptions as your as your sort of going through day to day work at a startup.

 

Johnathan Nightingale  

Yeah, there’s another bucket there too, which is that startups are – and this is true of non startup organizations, startups, just a lot of who we talked to, but – so much of building a business is starting from a blank piece of paper. It’s saying, “What are we here to do? How are we different from other people in the space? What’s the problem we’re trying to solve? How do we get customers to care about us?” Like, there’s so much where the there was no answer and so we had to make one up. And in most of building a business, that’s a true and righteous thing, right. What makes you different from other people is it’s not a question anybody else can answer for you. But what happens, partly because you building every other part of the business from scratch, and partly because often the founders have never gotten their own education on this stuff, is that the structure of the organization, the tempo we have for how we expect work to be delivered, the way that we approach hiring, the kind of culture we create, are also starting from a blank piece of paper. They’re not informed by what other companies have done or not done or if they arts, it’s the worst. It’s like, “Oh, I read that Netflix culture deck and we’re also going to be a professional sports team and fire people every 10 minutes.” Like, you can do these things where you just end up either inventing it from whole cloth and making a bunch of mistakes that you could have avoided with some study of history, or trying to copy somebody else’s culture. The danger of those culture decks is that their marketing documents, right, their job is to assist recruiting a particular kind of talent. They are somebody else’s highlight reel. You’re seeing a perfectly composed – and often beautifully visually designed and type set – story about what it is to work in a company. And that’s not the ground truth for every employee in that company. But you can’t see that. It’s like, it’s like looking at somebody else’s Instagram. You know that their Instagram is full of like, hyper polished, perfected images of their life. It would be a mistake, and there’s like a whole cottage industry about reminding people, it’s a mistake to view that as real life. But when we’re building a business, it’s so tempting to be like, “Well, they’ve got it figured out, let’s just do what they do.” And it blows up over and over again.

 

Christian McCarrick  

That’s an interesting point. And one of the reasons I enjoy doing this podcast is it’s sort of the grass isn’t always greener too. right. You know, you talk about that Instagram highlight reel. And I gave a talk at the end of last year, and I talked about, listen, what you see of people when they’re on stage, you’re like, “Oh, my gosh, this is amazing. Like, they’re so awesome. They’re perfect.” But it took them vomiting in the bathroom before that. It took, you know, sleepless night, and, you know,  hours and hours of shaking, giving presentations to come across that way. So what you see is like hours and hours of work that goes into being that – and you can certainly do that, too if that’s something you want to prioritize, right. As a leader too, is it sadistic to want to really kind of like that other teams are all screwed up too? I don’t know, maybe it’s not that but it makes me feel better that like, as you mentioned, I’m not the only one going crazy. Lots of people are having these struggles and it’s good to be reminded of that once in a while that like I’m not the only one.

 

Johnathan Nightingale  

One of the things we talked about when we when we’ve got teams managers in here, they’re sort of learning what their new job is, obviously, one of the things we have to talk about is firing. And when Melissa and I are talking to a group of people about that, we always ask, “How many of you have had to fire someone?” and two hands in a room of 20 go up, because a lot of managers, it’s the thing they’re really afraid of/ They’re hoping they don’t have to do it. They’re hoping HR does it before them. They’re hoping they can transfer the person without doing it, anything to get out of sitting in that room and ending someone’s employment. One of the things we do in that moment is we talked about how the first time I fired someone, I went out and threw up in the parking lot. Melissa and I only found out while doing content development for our programs that that she had basically the exact same experience.

 

Unknown Speaker  

Yeah,

 

Melissa Nightingale  

Yeah, I threw up in the women’s washroom is the first time I fired someody.

 

Johnathan Nightingale  

Iit’s not because that is the job of a manager. It’s not that the correct way to fire someone is definitely to vomit afterwards. But it’s like, it’s important to acknowledge that this stuff is very hard and in the moment where you’re firing someone, it’s not about you. It’s about the person who no longer has a job. How can you handle that process in a way that preserves their dignity and integrity and helps them understand what’s coming next. But in a room full of managers, it’s worth saying like, This is hard., and anybody who tells you that they’ve always had a disciplined and clean and strategic approach to this stuff  – I just don’t trust that it’s tough stuff.

 

Melissa Nightingale  

Yeah, one of the things that we come back to pretty regularly as a touchstone for Raw Signal Group and the work that we do here is “No natural leaders,” right? No one’s born knowing how to do this stuff. So somewhere between birth and your first management job and your first executive role, you figure some things out along the way, which means it’s learnable And so for leaders coming into our programs I think one of the things that really helps is that we didn’t feel like we knew how to do a lot of this when we were first starting out, and it is stuff where you can learn it and you can get better.

 

Unknown Speaker  

Mm hmm.

 

Christian McCarrick  

And hopefully with leaving not quite a large you know, stream of dead kittens along the way right in which is hopefully avoidable, but not always.

 

Johnathan Nightingale  

Yeah, yeah. That’s it. I think that’s a big piece of it, you know, how much of this can we actually sidestep with training? How much of this like Raw Signal Group shouldn’t exist if the only way to learn how to fire someone is to do it terribly eight times before you figure it out. Like, our whole point is, can we equip you with some of these skills ahead of time and, and we believe, obviously,  that we can, that it’s a thing you can learn.

 

Christian McCarrick  

I totally support companies like yours doing that, like wholeheartedly and I support my, my current managers, my future managers and people that are just thinking about getting into management or leadership today do that, because, for me, it’s that virtuous cycle, right? So if more people get more aware of learning then I might actually be able to hire people that have actually had the skills that weren’t learned. I mean, everyone’s gonna have on the battlefield type of skills right on the job, you’re gonna have to work through stuff, but the more we can, as you mentioned previously, learn from others who have made those mistakes to not repeat the mistakes then that’s better for us and the whole industry.

 

Johnathan Nightingale  

Absolutely.

 

Christian McCarrick  

Most of my listeners here are, you know, getting into managers, new managers or in some cases have been managed for a while, but like everyone hey there’s still things we can learn. Focusing on the kind of the new manager role or someone taking over a new team or going to new company, what do you think is the most important thing for a manager coming in to that role to focus on, say the first 90 days that you’ve seen that maybe just hands down, it has the most impact?

 

Johnathan Nightingale  

I wonder if I have the same answer?

 

Melissa Nightingale  

Yeah, I mean, I would say if you’ve got 90 days to have impact, the most important thing you can do is start having your one on ones on a regular basis. Especially if you’re you’re sort of leading a new team, the trust that gets established when you’re having regular points of contact with your team, the information that starts flowing bi-directionally right, that from the top down, and from the bottom up, you end up with a much better picture of the problems that you’re trying to solve. Not only sort of the strategic problems that you’re trying to solve, but also from a human perspective, right. Sometimes when you’re managing a new team or you’re stepping into management of a team that was inherited right, the team existed before you were managing that team. You may think you’ve got a clear idea of sort of what you’re walking into, but I would say one on ones are really good way to make sure that you’ve got a pulse of the organization and the team within that organization.

 

Johnathan Nightingale  

Well, I definitely agree with that. Well, so I think I think the most important thing to do in the first 90 days is definitely to have those one on ones it correlates with everything good about organizations. I think probably the most important question to answer for yourself is “What is my team here to do?” And the reason I would lean on that is that you know, Christian, when you talk about the listeners to the podcast are getting into management or maybe you’ve been in it for a while, I would say that a lot of people when they’re finding their management presence, when they’re finding their style and developing it and deepening their craft, a thing happens, where some portion of them, I think in engineering probably 60 to 70% of them, start to focus a lot on the practices of management. One on ones, holding space for my team to ask hard questions, mentoring, working with them on problems, doing career pathing – and they can lose the plot on the fact that your team is here to do a thing. And I was one of these. So I’m not coming from a judging place. People ask all the time, “Why does the book sound angry?” The book’s not angry at you. The book is angry at us. This thing where you’re sitting and having these deep searching conversations with your team but you don’t have a clear idea about like, “Why are there eight people on payroll? What does success look like for your team”? I’ve seen more managers fall into that trap. I’ve seen directors with big organizations have to be fired because their team loved them but the rest of the organization refused to work with that team anymore because they were so caught up in the conferences they wanted to go to, and the new techniques they wanted to try, and the refactoring they wanted to do, that they weren’t doing anything for the business, and I’m not trying to be cold and harshly capitalist here, I’m saying that like it does your team no favors over the long run, to indulge all of that stuff to the exclusion of doing work.  And that may be obvious to some people but I will say like, I definitely did it. I definitely had a team where I cared a lot about my relationship with them as a manager, I cared a lot that they liked me as a boss. And the result was that when I was hearing stuff from my own superiors, or from other part of the org, about where my team wasn’t pulling their weight, I shielded them all from it, because I didn’t want to jeopardize the relationship, because I didn’t want to be the bearer of that criticism, and it made my team much less effective and then I was a much less effective leader. It took me a while to wake up to the fact that I wasn’t helping my team in that moment.

 

Christian McCarrick  

That’s a good point that a lot of people need to understand. What’s the context of your team? What’s the business driver behind it? Your company is in existence to provide value to its users. Right? And who are those users? How is your team ultimately providing its piece of that value to the users?

 

Johnathan Nightingale  

Yeah, yeah. And I’d say, you know, we joke about it with managers like, I think management is a is a real first class job. I think it’s nothing to be ashamed of, I think it’s a fine profession to pursue. But we joke about the fact that like, I know what your engineers are here for, right? They write software. They can write the right software, the wrong software, but I am confident that they’re earning their paycheck. I’m very curious about whether you’re earning yours, right? Because you’re not writing any software for me, you’re not even writing any marketing copy for me, right? You’re not doing the individual trades, and many of them are many of them are day shifting and night shifting, but at least in theory, a manager is not doing that work, so help me understand why we’re paying you. We can pay another engineer sometimes, depending on your compensation strategy we could pay two or three engineers for what we’re paying a manager or a director. So why are you here? When we say it, some of them get this look of terror because this is the thing they’ve been worrying about that someone would figure out that like, this is the sham job and we try to discharge that tension? It’s okay, there’s an answer. The answer is that eight brilliant engineers, working in the same office, in the context of a business will generate so many incredible ideas and so many adventures and explore so many different solutions to problems, that you will only probably get three or four engineers with a forward motion out of them. It’s not because they’re bad or lazy, or any of that it’s the opposite. It’s that they’ve got such creative energy, that they will go in too many directions at once. Right, your job is not to smack them or to take away their creativity or any of that nonsense, but your job is to align them and motivate them and help them connect their work to the business and connect their creativity to the hard problems we’re trying to solve for our customers or our nonprofit clients or whatever the context is. That’s what gets you paid, right? If you can turn eight engineers of payroll into eight engineers of output, that’s a miracle that’s never happened spontaneously in the history of engineering. It’s worth paying you for that. But don’t take your eye off the prize, that’s your job. What is your team here to do? And are you doing your job of making them more effective at it?

 

Christian McCarrick  

And going back to your previous point, the more effective that the rest of the organization also views your team, the more leeway as a manager you have in allowing them to do things like go to conferences, and whatever the things that they think are important to them, you know, work half a day on Fridays, or do hackathons all the time. Because if you’re producing, you’re bringing that value, the rest of the org is sort of like, “Hey, this team is a high functioning team, they’re producing, they’re valuable, they seem cohesive, let’s let them do what they want.” Right. So it’s another good aspect for that.

 

Johnathan Nightingale  

In the early days of my time at Mozilla, and Melissa’s time, it was all as well, Melissa was really a standout leader in her organization because she was running a piece of the marketing organization, but she was running a piece of the marketing organization that the engineers would not engage very much with the concept of marketing, right, who are who are pretty new to it and could have used some more education on it – we knew what Melissa’s team did.

 

Melissa Nightingale  

It was a little bit unfair because I used to write software, right. So like, if you got a marketing leader who used to do engineering work, it’s a little bit of a hack, because you tend to be able to shake hands and talk to those people and understand the value of each other’s work a lot more easily.

 

Johnathan Nightingale  

Yeah, I think in general, a lot of startups that are engineering led, and Mozilla wasn’t a startup but function very much like an engineering lead startup, really diminish the work of marketing teams and other teams and some of that is about just one function, not understanding another function and a lot of it is about misogyny and shitty behavior and needs to be stamped out. But at the core, there’s a thing that you said, that really resonated for me, which is that when the rest of the organization can see that you’re driving, that your team is an effective team, that it’s doing good work, things get so much easier for you, as a manager, you start solving higher quality problems, like “How do we find new opportunities for the people on my team that are growing so quickly? And we’re being asked to do more work because we’re effective at it and how do we scale to meet those challenges?” Those are much better problems to solve, then why do we need a budget for this team at all?

 

Melissa Nightingale  

But I’d add, especially if you’ve got folks who are listening who are newer in their management careers, like one of the most amazing things you can do for yourself and for your organization is if you’ve got areas of the business that you don’t understand, or even ones where you’re inclined to think you could fire that team and not miss them, those are great opportunities to go – one say hello, and two – get yourself educated, go learn what those folks do for the business because either you’re totally right, and they don’t do anything core to the business…

 

Johnathan Nightingale  

And you are the first genius to ever noticed that.

 

Unknown Speaker  

sure

 

Melissa Nightingale  

Sure, possibly, or you’ve got a massive gap in how you think about your business. And chances are, I would say it’s probably the latter. And what an amazing gift for yourself as a leader to get rounded out and get educated on it. It will make it so much easier for you to not only represent the concerns and the sort of strategic objectives of the business as a whole, but also make it so much easier for your team to work with that team because you know, the areas of interlock, you’ve got clarity around, this is how we plug in, yes, like, I’m on the engineering team and that person’s leaving finance and we don’t have a whole lot of time when we’re in the same meetings at the same time, but there are areas where we’re going to need to work together and we’re going to need to think about each other’s sort of functional areas. And if we’ve got an understanding of what that means, then when I encounter like, oh, we’re we’re sort of shifting over to AWS, and it has the following impact for a budget, I know how to go find you and have that conversation before I signed the contract.

 

Johnathan Nightingale  

Yeah, you asked about traps of startups in general, I would say that the number one flag of an executive who’s who’s thinking too Junior, is when they’re proud that their team works the hardest, or proud that their team hits their goals even when everybody else doesn’t. Aat any management level, really, but especially as a as an executive in the organization, iIf you’re patting yourself on the back for being part of a failing management team, because you feel like at least you’re the standout on that team, you’ve got to ask yourself some hard questions about- to Melissa’s point – where your gaps in comprehension are.

 

Melissa Nightingale  

Yeah, one of the things we say to leaders, particularly startup leaders is that allthe interesting work within your organization is going to happen at the intersection of more than one team. And so if you’re spending all of your time, focused sort of downward on your own individual team, and none of your time looking across or looking up, you’re probably missing really important things that you need to do your job well.

 

Christian McCarrick  

Right. It’s not about optimizing your team, it’s about optimizing the score for the entire organization, right. That’s how you’re going to have success, right, and sometimes have to sub optimize teams, just like systems, in order to optimize the whole,

 

Melissa Nightingale  

It’s so hard to know that the first time you get promoted, especially if you were a peer and now you’re a boss, like so much of your identity is in relation to the people on your team and not across the org. And so I think until someone actually sort of shakes you and says thay, it’s one of those things that like, yes, you can sort of say it is true, but you don’t really live it until you sort of pick your head up and understand the importance of it.

 

Christian McCarrick  

True. So you’ve published a book you’ve referenced it a couple of times in our conversation, it’s called, “How fucked up is your management? An uncomfortable conversation about modern management.” And for my listeners, some of the chapters are,”Why it’s a mistake to hire superheroes,” “Unlimited vacation and other forms of guilt management,” and “Is it worth your time to be excellent?”

 

I’ll post this on our show notes, on SimpleLeadership.io and you can look at this. It’s on Amazon, also, but I want to talk about one of the chapters here. You talk about “Leadership is not about your good intentions.” So what does that mean for these listeners? Because I think we hear a lot about oh, I had good intentions – and that could be about leadership, it could be about diversity and inclusion , it could be about lots of things. But for you, how did you define that when it was that important?

 

Johnathan Nightingale  

Oh, yeah. Well, this one might make me controversial. I don’t know. There’s a saying there’s a cultural touchstone that a lot of companies have where they say, you know, assume best intent. And we had it for a while there was a there was a leader at Mozilla who espoused it and I thought it was a pretty good idea, and I don’t, I don’t. And I get why people adopt it. They want to anticipate that like, conflict about the substance of a disagreement is ok, but like, don’t assume that your colleagues are out to hurt you, don’t assume that this was said in malice when I might have been said in ignorance. Okay, fine. I think if you want to have a value around, don’t assume something was in malice when it could have been ignorance, that’s okay. But intent – intent is a funny word. Intent is is something that we fall back on as a defense, right? You say something that’s, racist, or that’s ableist or whatever, and somebody calls you out on it and you say, “Oh, come on, that’s not what I intended. You know, that’s not what I intended.” And I think it’s a way to avoid accountability. Right? I think we’re ll learning I’m certainly learning, how to be a better human on this, how to communicate in ways that that are – more inclusive, but more generally, like just how to understand how much of the way we do business is baked into a bunch of assumptions that everybody looks like me, right that everybody’s going to be a straight, white, English-speaking non-immigrant guy. And I find that in that context, anytime I feel like saying, “Oh, that wasn’t my intent,” I’m mostly hurt that someone called me out on something, and I want a way to save face, I want a way to, to remind everyone that I’m not a bad person. And it would be so much more productive every time that happens for me or for any leader there to just be like, “Hmm, yep, screw that up. “That’s it. Not like I need to crawl into a cave and never come out again. “Yeah, that’s a good point. I did not notice. It’s lazy language that I said that that way or that I didn’t invite you to that thing, or whatever it is. That was my own failing, and I’m going to do better.” I don’t think that’s such a hard thing. But people feel like it’s a much deeper attack and they use this intent based language a lot. And, to me, what I want to get into leaders’ heads is that there’s almost no case I can think of with that should be the way you open your response to someone calling you on something.

 

Christian McCarrick  

We talked about that sometimes to me as an example. I didn’t mean to step on your toes and break it, but I broke it, and the damage is done. So, you know, we need to deal with that in a way that helps us to move forward and, you know, damage is done. So how do we own up to that and make sure we find ways to make sure it doesn’t happen again.

 

Johnathan Nightingale  

I’ll add one thing and then I’ll shut up, particularly any listeners, you’ve got of your podcast who are like me – straight white male engineers coming up in tech leadership –  I will say that like, my own experiences, one of those is that “I’m sorry, I fucked up. Thank you for calling it out. I’m gonna try to do better.” That is a skill. People are like, “Why can’t you just say sorry?”, it’s just so like, just don’t fight the accusation. Just say, “Okay, I got it” That takes practice. It is uncomfortable to be challenged that way and it is not something that I got a lot of exposure to coming up, right? Because most of the systems were built for me. That takes practice, but that practice is worth doing. And like, if “intent” is the word that helps you hear it, then great, but that practice is important.

 

Melissa Nightingale  

The only other thing that I’d add is that we, as leaders, I think, get really accustomed to the idea that in many cases, effort isn’t sufficient, right? That as a leader of a team of people you can say, “I tried really hard, but missed,” once, maybe twice, but but most of the measurement of your success within the organization is like,”Did you do the thing that you said you were going to do?” Not, “Did you intend to do it? But did you actually do it?” And I think for many aspects of leadership, that’s what you’re looking for. It’s not the effort, but the outcome. And I think it’s totally right that if you are held to higher account within your organization, if you have that outsized responsibility of leadership, if you have that outsized visibility and impact of leadership, then surely what should extend to your behavior that you are  holding yourself to account for not only what you intended, but the outcome.

 

Johnathan Nightingale  

And what a great opportunity to model that for the rest of your team too.

 

Christian McCarrick  

Yeah, exactly. As I was looking through some of the posts that you have on your blog, I don’t think I’ve ever had a discussion topic on the podcast where we talked about family planning, returning to work after maternity leave. And, you know, I think this is a topic that clearly if it hasn’t been discussed on my show, it needs more attention needs more work, and especially if you want to support more women and balanced families, you know, in technology and the fields that we’re in, and not just tech, I think, in general, but you know, especially in tech for the listeners of this podcast, Melissa, what are the things that you know, is not to go through your whole blog post, but how can we bring more to this conversation? How can we as managers and as leaders support this moving forward in organizations?

 

Melissa Nightingale  

Christian, I love that question. It clearly touched a nerve at the time that I was writing those posts. I wrote them, in part because I felt like the conversation wasn’t happening. It was happening sort of in individual one to one context, but there wasn’t a lot out there when I was trying to navigate my maternity leave, while working as an executive at a startup, it just felt almost impossible and short of looking for folks I knew who had been through exactly the same thing, it was really hard to find information. One of the things that’s neat is that that series of posts around family planning, around mat leave, around parenting in a startup, continue to be ones that people really respond to, right. I think folks in very similar situations, say, “I was looking for anything at all that I could grab on to, I’m the only or first parent in my startup, and no one else seems to understand what that’s like.” They continue to be ones where I get notes from from parents saying, “Thank you for writing it.” One of the things that’s happened since I originally wrote those posts is that a group in Toronto actually put out something called “The Parenting Playbook,” and it’s a really detailed guide for startups around how to incorporate more parent friendly policies into their workplace, and how to help parents not only, sort of in terms of comforting and supporting them when they’re taking leave, but also how to reintigrate them back into a fast moving environment when they come back from leave. And so if you’ve got folks who are trying to either navigate that themselves or navigate that for their teams or get educated so that they’re sort of trained up before they need to know that information, “The Parenting Playbook” is fabulous, fabulous, fabulous, and a wonderful resource and I wish it had existed years ago, but it does now.

 

Christian McCarrick  

Okay, so for that,  I’ll put it in the show notes so that people can find that online as well. And I will certainly, if no one to ask about that, too. I will certainly try to promote that as well. So thank you for that piece of information. And, you know, this probably warrants a whole nother episode, which I might look into doing in the future.

 

Really quick: Give me an elevator pitch for Raw Signal ? Your tagline is, “We build better bosses.” So give me the 90 second pitch, like why and how you can help our managers and tech leaders out there today.

 

Johnathan Nightingale  

90 seconds. Let’s see. I think we can do it faster than that, because we’ve already had 45 minutes of everyone’s ears. “We build better bosses.” We chose those words on purpose because bosses come in a lot of different forms, because you’re never done. “Better” is our goal not best. And we “build” because this is loanable. We do this thing on some of our management programs where we start by asking a set of questions like, “Would you agree that you know how to run an effective meeting? Do you know what a one on one is for? Do you know how to give hard feedback?” And for most of the people coming into our program? The answer is, “No.” The answer is, ” don’t know any of that stuff. Because I’ve never been taught.” In fact, when we interview our participants before they start, 85% of them have never had any prior management training at all. And that’s true at the executive level. And that’s true at the entry level team lead. You can get better at this. You don’t have to work with us if you don’t want to, all I would say is if you’re in a context where you’re like, “Yeah, I believe I want to get better at this!” Great. Find people who have actually worked in the field. The number one reason training fails is that it’s not relevant, and a lot of training dollars disappear into stuff that people can never apply. But when you find people who understand your business and can actually speak to you at a level that’s useful, you can get so much better at this and your organization just it’s a transformative moment. For us, it often comes in crisis, we get people calling because they just got Culture Amp scores that were a disaster, or because they just had their third person quit in two weeks.

 

Melissa Nightingale  

Or because they just raised their “B” and they’re about to triple in size and that feels really daunting because. “we’re 40 people in the rocky and I don’t know what that’s going to feel like at the end of 2019. “Those calls… we know because we’ve been there.

 

Johnathan Nightingale  

Yeah, I think that’s our pitching a nutshell.

 

Christian McCarrick  

Awesome. And something I asked all of my guests on the show. We’ve mentioned a few you have your book, you mentioned that family planning guide and going back to work, Melissa, any other recommendations, books, videos, etc, that you would recommend to managers trying to level up a bit out there?

 

Melissa Nightingale  

Twice a month we can be in your inbox. We have a newsletter about management and leadership and in one of my favorite moments, my mom actually forwarded me my own newsletter, and was like, “Hey, this is a really great newsletter, you should subscribe.” And I was like, “Mom, like, that’s our newsletter!” And so I feel like you know, my mom is not a tech person. But in terms of ringing endorsement, having your own parent forward you your own newsletter and say, “This is great.” You know, tell your listeners, my mom thinks it’s great.

 

Johnathan Nightingale  

And in terms of other readings and books around the world, we’re huge fans of everything Ijeoma Oluo writes and she’s got a book called, “So you want to talk about race?” which is quite helpful if you’re sort of engaging with those topics for the first time . If the intent conversation set off your radar and you’re like, how do I get better at that? Ijeoma’ s book is a good one.

 

Melissa Nightingale  

We both really enjoyed Priya Parker’s “The art of gathering,” in part because I think it’s a non tech take. Like Priya works with startups but it’s a lot around how you get people together and build intention into the sort of advanced planning before they’re in the room and what that’s going to feel like. And I think for many startups we’re doing, we’re doing a lot of f sights, we’re doing a lot of all hands, we’re doing a lot of team meetings and I think any leader who’s sort of facing down either the first one or the first one that needs to go really well would benefit from reading that.

 

Christian McCarrick  

Awesome. What are the best ways to contact you to read your blogs, to contact you for you know, helping their org, you know, and if you can spell anything out for the listeners to, we’ll put them in the show notes, but what’s the best way to contact you?

 

Johnathan Nightingale  

We’re both Twitter people on because we like arguing with strangers more than arguing with friends. otherwise, we’d be on Facebook. But you can find us on Twitter. I’m @Johnath,

 

Unknown Speaker  

and a th

 

Melissa Nightingale  

I’m @Shappy.

 

Unknown Speaker  

y.

 

Johnathan Nightingale  

And then if you want to find our website or get in touch with us in a professional capacity, we’re RawSignal.ca – we’re in Canada so your.com habit will get you somewhere else. I don’t know where that gets you. RawSignal.ca gets you to us.

 

Christian McCarrick  

Melissa, Jonathan, it’s been a real pleasure having this conversation with you today. Thank you very much for your time and you know, have a great rest of your day and the rest of your week.