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.