Chris is a Staff Engineer at HelloSign, a Y Combinator eSignature startup in San Francisco. He got his bachelor’s degree in computer science at the University of Colorado in 2001 and started as an embedded systems analyst for FedEx, building software for handheld scanners in FORTH. In 2004, he graduated with an MBA in software project management from Colorado Technical University, but decided to continue as an individual contributor, joining the defense contracting world to build geospatial modeling software for Northrop Grumman and British Aerospace. He transitioned to the world of commercial software in 2010, contracting with companies such as Pearson Publishing and the City of San Jose to build custom content management systems based on the open-source CMS, Alfresco. In 2012, he moved to San Francisco with the dream of working at a Silicon Valley startup and joined HelloSign in 2014. Chris is currently responsible for technical leadership across 3 products at HelloSign, and also spent 2 years managing 8 engineers at the early-stage startup before stepping into the Staff Engineering role as an individual contributor.
- Website: https://hakuna-
- LinkedIn: https://www.
- Twitter: @idiosynchris
[0:11] If I move this up here I’ll be able to just kind of reference it.
[0:19] Good afternoon Chris welcome to the show Absolutely and I’m excited again you’re coming into the office I always love and gas coming to my office because you cannot get to see people face-to-face I think it gives a little bit in a more personal experience.
[0:33] It’s pretty phenomenal I was originally going to come in or speak with you remotely and listen to some of your podcast and the other guests were talking about how beautiful of you is and I have to attached it is pretty amazing.
[0:44] So for all you out there who want to be a guest right if you can make it to San Francisco or I come on in or even if you don’t to be guests coming in we can grab beers or something always willing to meet.
Are there injury managers and people who kind of care about helping to improve as I say that the craft of injury management and instead of helping with engineering leadership so,
Chris little bit of background about yourself kind of where you are now had you get there when we start with that.
[1:07] Church so right now I’m a Staff engineer with hellosign which is an e-signature company or Y combinator startup started in 2011.
We originally hellofax and pivoted to East signatures probably in 2013.
[1:22] And if used your product so yeah yeah.
[1:24] Have a great team of Engineers I would say there’s about 8-9 engineers,
tell her I know where we’re growing and yes I sometimes this track but yeah the teams ever revolving and so right now I’m,
staff engineer II kind of oversee technical leadership in architecture and design for multiple products.
[1:48] Great and you’ve been hello son for a while then write comparative Lee in and kind of Valley speaker.
[1:53] Yeah I have been there since January 2014 on start on Tuesday and yeah I guess that’s long and.
[2:00] And you started there where you and image of contributor when you started yeah.
[2:06] Yes yes I started there as a full stack developer I was looking for something in the startup world I was an independent contractor for a couple years before that and was looking to work with a team.
And kind of stumbled upon the job posting on Hacker News accidentally.
Applied and about a. 3 days later I had it off her stuff went ahead and accepted and you have been a fun ride ever since.
[2:33] And I think that’s for for engineering managers out there too or looking to hire talent I think sometimes Hacker News as a way to actively seek you know post job listings or something on there is is overlooked.
And I think that.
When in this in this kind of environment when it’s kind of hard and challenging to find people investigating all your sources for trying to hire and I know hacker you Hacker News AngelList a couple other wants to maybe not traditional job boards to try to get people.
[3:00] Right I wasn’t even following it for the job postings I was just keeping up with news.
[3:04] That’s right that’s right and so from Individual contributor you can you grow into manager there will have the head of that path happen.
[3:11] Right so about October 2014 I’ve been there for about 10 months and the team had grown on so that we were five when I started in January.
And had hired a couple more Engineers I think we are about at 8 in October and the city O’Neal had asked me to,
you know step in as as a manager to kind of help him on he definitely saw that in order for the company to grow in order for the engineering team to grow we would need Management’s which he was doing,
honored percent of the time,
and so in order for him to juggle both you know co-founder responsibilities and CTO responsibilities he needed somebody to take over the management portion which I seem to be a natural fit for on paper I’d never manage the team before,
but I had the most industry experience I had an MBA and so.
Yeah it would it just seemed natural to ask me if I was interested in stepping into the role and I actually wasn’t sure at first because for a really long time actually when I first start out as a software developer I was very interested I would never go into management ever.
And and that lasted me probably about 17 18 years and and I can’t I think I got to the point where I.
Realize I was I was hiring other engineers and I was noticing resumes of people who had been working for no decades at a time.
If they have never let Amanda team I would have thought that was kind of suspicious and so you know what kind of self reflected and thought okay I think this is time for me to at least explore.
[4:48] . and yeah I thought it over the weekend and came back and I said yep I’m ready to try this out let’s let’s go.
[4:55] Which is how I find a lot of things go right I always took the antidote ready to go to whether it’s grad school or CS you get a degree your coding for x-ray years and suddenly on a Friday your coder on a Monday your manager.
[5:09] That’s pretty much how I want ya.
[5:11] With with hardly any in a background there for you I want to go back to something you mentioned you got your MBA what should what was the drive for you to go get your MBA and what was the goal for doing that.
[5:25] So my first job out of college was with FedEx and I was developing on software for handheld tracking devices at the careers use.
Tax is a great company they have a lot of resources and so one of those benefits I had,
I’m at my disposal was an education program on site at my office and so I know getting my MBA and I didn’t have to,
go anywhere special I got it over my lunch break took me about 2 years to complete and.
I graduated with a emphasis in project management software project management and the next step for me out of that would have been to get my PMP my professional or project management professional certification.
And kind of preparing for that made me realize like I really don’t want to do this I want to stay Technical and and I was kind of when I made that ultimatum to myself like I’m never going into manager that I’m going to stay by City forever.
[6:21] Which is interesting I mean there are very few I think software engineers and even suffering HR managers and leaders that actually have an MBA.
I did a fireside chat couple weeks ago with Nick Caldwell VP of Reddit and you know he actually.
Has an NBA is well and there was some you know he we talked a little about.
Did you going to management it is that a plus some people out here he’s made fun of some deal here Below in spite of you having an NBA kind of said but you know he got it at Microsoft and they also provided you know that type of assistance as well.
And I think so she’s going to go into larger companies having that business aspect where are the helps at least doing your MBA term.
You probably even heard the words management some of the things that go into it or a lot of other suffering in years that become managers don’t even have that.
[7:12] I’ll be honest when I took my NBA courses I would say a lot of it kind of was like water off a duck’s back for me because I didn’t have the real life experience to understand a lot of the things lot of the concepts I was learning about.
I understood them theoretically but I couldn’t apply them or connect the dots two real world examples and so yeah I I sort of wished I hadn’t done it so early but.
Yeah I would like to have to revisit some of that at some point.
Same thing with my computer science degree I would it I mean a lot of the operating system stuff that I learned and compiler design stuff that I learned.
Probably out of date by this point.
[7:48] But yeah I know no good and then so kind of get back in the seat to ask you to take over some of the management stuff you jumped right into it did you have any you know how did you.
How did you handle that the Japanese resources is there any training that he needed was in a rementer ship at all.
[8:05] I think the most most of the support that I got was from a voracious amount of reading that I did.
Neal’s great RC too I reported directly to him he you know has been managing the team himself so he had a bit of experience there but he even met that he would have liked to have,
you know been able to provide Management training management mentorship that’s something that I would have like to have had maybe outside of the company,
we did not have a lot of managers at hello sign at the time we were 20% company so actually even considering.
You know promoting me to Natural hiring manager seemed sort of Blossom this and you know from the start of perspective like how you’re so small like you don’t need a manager yet.
But I yeah I would have liked to have more mentorship and and the reading definitely helped but you know having somebody to sort of bounce ideas off of and.
You know sir to do hypotheticals with and.
You know I have this this happen out on the team the other day and I responded this way is there a way I could have responded better in so Neil provided that kind of.
I’m sounding board for me for a long time and I was also able to eventually develop relationships with other managers that we ended up hiring after me.
Down the road I did get that mentorship in other forms.
[9:37] I was like to ask any guessing to show any major mistakes you made that you look back on noun cringe over.
[9:42] Oh yeah lots lots and lots of mistakes.
[9:45] At the expensive before employees.
[9:47] Right right well actually that blog post that I think you’ve contacted me over which is.
You know tips for new engineering managers. Was born out of all of the mistakes that I made and I had ended up learning over the course of my two years managing the team I need to write down everything and so.
Towards the end of my career as a manager I went through all my notes and I was like well I have a lot of good information here I’m going to put this in a blog post and so.
Yeah. That was basically born out of my mistake so I would say that the few key mistakes I could mention here is is I wished I had spent last time coding and more time actually paying attention to the team.
Things were always really hectic I was juggling a ton of stuff when you have a direct reports.
You basically have to keep a contacts in your head,
for each of them cuz they’re yuchun unique and you have to remember you know what’s going on with each person and juggling. And then also you know trying to maintain your devil osity that your personal devil Aussie is really difficult.
Until I wished I had you know taking a step back and.
I don’t need to put my headphones on right now I don’t need to do that ticket.
I can I can delegate that to somebody and I can focus on this other person over here is doing really great job and you know I want to you know give them feedback about that or whatever.
[11:16] That’s extremely common I think that the.
New managers thinking that they you know they still have to be the technical lead on the team making on the Tekken decisions being you know hands in sort of the code all the time.
Is probably one of the biggest items that I see that people have the hardest time letting go of right but it’s probably the.
[11:37] Yeah it’s.
[11:37] You mentioned they should let go I don’t make a pletely.
You don’t put yourself in the critical Path of Neo release where because if you’re going to hold up the release the 101 is pregnant suffer or at you going to cancel it.
To get the release out but ultimately you do that too many times and you don’t have a team so what you know we go through serve the place and I did I found you.
I kind of threw the blog post you wrote and I’ll have all the information and the links to that on my show notes and we can talk about how to contact you sort of at the end.
You do right down right down your your decision-making process and write down everything right did you ever get burned by but not running something done.
[12:21] That’s a great question I wouldn’t say I got burned necessarily but there were certainly times where for example if you’re working with a report and your maybe working through a performance Improvement plan,
like having those decisions written down is is critical I mean if if you.
If you miss something and you’re trying to remember what was said at [1:01] a month ago you know that,
that can reckon you know impact somebody’s career pretty significantly so you know that’s that’s an extreme example but other examples are,
ended up using an online tool called Lighthouse which is a way to manage your notes when you’re having one on ones with your reports and.
One of the really nice things was it gives you a section to put in my personal details like what’s their spouses name,
and for one of my employees I actually forgot to write that down and a couple months later I’m like oh crap you know,
who who who got spouse and so I went back and looked at my house and I hadn’t written it down so I guess that’s the most burned I’ve gotten.
[13:32] You don’t remember the kids names are this and if they have a spouse or not those will important things and I mean that’s a good point I think.
You found a tool that there’s there’s Lighthouse a couple other ones out there I think 15-5 is another one you know that we use in here.
And writing that down I think it is incredibly boring and you mentioned to and it comes time to whether it’s performance issues.
Or review items I think it’s important for the good in the bad because of the end of the year.
You don’t want to focus on with it didn’t do but I think it’s is as a way to reach out to employees and show even their compliments over the year.
Cuz it’s easy to forget to go in the bed and at the end whether it’s for a performance or just to make them kind of feel the sense of achievement and accomplishment to go back and say well you know what a great year you’ve had in here are some of the highlights.
[14:18] That’s all that’s a great point I mean when.
You’re doing annual reviews and having to think over the past year what did this person out of your team of a people do.
I mean I spent many nights like coming through get commit history trying to figure out what K what did this developer commits over the year so yeah if you write down everything it’ll it’ll save you a lot of time.
[14:41] If anyone out there to is an employee helping to keep a journal or notes yourself that you can email to your manager at review time I mean that’s kudos.
[14:51] Sprite and a lighthouse takes care of that for you too.
[14:53] So that’s awesome new thing you talk about is convening yourself to your team daily kind of what is that mean to you and why did you put that in there was in it as an important thing.
[15:02] Well for me it was related to the fact that my safe space is like being alone coating like headphones on not paying attention to anyone else I just getting into that flow Zone and.
And impound out the code so.
Yeah I had to consciously remind myself like this is not your job you need to be working with the team you know your impact is is based on your team’s impact so,
are they as effective as they could be are they working as efficiently as they could be in so just consciously RI committing myself to that.
How to set up a calendar reminder.
[15:40] Yeah. That’s true and would you consider self more of that kind of introverted side than extroverted.
[15:45] I think I lean more introverted but I definitely am pretty social so but yeah I get my energy from being alone.
[15:53] From yeah yeah which is which is I think hard because it specially when you have.
You know a bad day and I didn’t have any to work and you come in and and I’ve noticed here and I just hear other places to that.
As a is assertive manager or leader an organization people also pick up on your your moods right whether whether or not you mean them to be the case if I come in.
And if I’m feeling maybe you can something out of work affects me a little negatively no I’m not saying it then I like.
Why is Christian upset today like did I do something bad like it’s a company going to fold there it’s like no I didn’t get any sleep last night cuz my kid was that right.
But at the end I think it does take that conscious thought to say well the team is here they did me I got to put my you know crap on the back burner and deal with them.
[16:39] Process you know I mean this is always a good one right because.
Engineers to the for the most part think a lot of process is like the Dilbert manager and you putting these things in place just because you’re a manager now and you feel like I have to get stuff done so.
I mean there is some process it’s important right and so how do you can you talk about this how do you learn how did you go about getting buying and putting in process that was helpful for efficiency in thing.
[17:05] Chorizo when I started at hello sign we had very little process we basically tracked our tickets and fog bugs and.
We kind of arbitrarily decided when we’re going to have a release and you know we come four years later we’re we’re now HIPAA compliance talk to you compliant and so we went from one extreme to the other.
I’ve been fortunate to,
what kind of watch us grow through that really awkward phase where you know I was kind of contributing to the development of the software development life cycle process will you move to jira,
and fortunately hired a really great manager with lots of experience who had worked with cheer in the past brought out he was able to really own that and kind of develop.
That even further from where I left off and so yeah when we brought in a lot of expertise to assist us with that.
But yeah from a developer standpoint.
You know process is kind of the enemy I was like kind of getting in your way of actually getting your work done but I think it’s important for managers and developers like to understand that,
you can’t work as a team unless you have that process in place you can’t you know achieved things like the compliance without that process in place.
I’m sorry it’s it’s important to be a champion for the process cuz a lot of the times your teammates.
[18:36] Are not going to be there going to push real hard against it and you’re going to have to say no this is important this is actually for the benefit of all of us and.
[18:45] Yeah well plus having to do things like sock and HIPAA right Munoz.
There’s not much convincing you should have to do I’m in your hands are tied at that point right there is a certain set of process especially around.
Compliance in change management right and you just have to do with those that believe me I know you’re going through that here in the past and it is.
It is definitely challenging right if you put it in there the next thing you talk about and I think and I totally agree this one you know scheduling that time to plan.
How did you do you actually do like calendar blocking and time boxing and every actually put on your calendar and said this is the time I’m going to spend doing this.
[19:24] Yeah so one thing that really helped me I live in die by my calendar I ended up setting up time at the beginning of every day like 5 minutes everyday to plan what I was working the day setup.
At least a block of 15 minutes on Friday to review what I done and plans the next week and then at the beginning,
I can remember since the beginning of the end of every month I’d have a 30-minute block where I would say okay what’s my monthly goal.
What about a Kohl’s sell yeah. That really helped just to kind of like make space for that otherwise yeah you wouldn’t probably do it.
[20:01] Any other tips you have or guidelines for not just managers but for even managers helping their direct reports on time management General.
[20:10] That’s a really good question I feel like I’ve worked with some of my teammates on you know doing time management and for me it just comes down to actually making the making a calendar your priority in life.
You know putting it up where you can always see it making sure that if if you plan something it immediately goes in the calendar.
Yeah until I actually started managing I was not a big calendar user but now I don’t know if I could live with.
[20:43] No I mean it’s true you look at mine it’s it’s like blocked out crazy right I haven’t put like my gym time on there.
[20:48] Yeah you can’t juggle that stuff in their head.
[20:50] And you know I think one thing that goes along with time management and it kind of goes on with your next point is about distractions so how do you.
As a manager help to stop distractions from your team right and keeping them Coco in the flow.
[21:05] What are the things that we had works and we’re still kind of working through is developing channels for information to flow into the engineering team and also come out of the engineering team.
The startup you know originally we were in a warehouse space for everyone just kind of works together and so distractions are pretty common.
And so for our current situation you know as weak as we grow and we hire more people those lines of communication increase and and and you really want.
That kind of workplace or that kind of communication to to be more focused otherwise,
your developers are never going to have time to do work so one of the things that we ended up doing was building a,
sort of service desk like ticketing scheme or taking process where if somebody across the company had a quite like a technical question about.
How does the product work or why is this customers no date of doing this or you know how does this plan work with us feed these features.
They would end up submitting a ticket and it can be prioritized and it tracked and and multiple people can contribute to it and so that’s helped and you know there’s a little bit of overhead there but.
Yeah that’s helps kind of reduce distraction because then we can you know say.
Hey Nick can you monitor that Q this week and everyone else can kind of focus on actual actually doing development.
[22:39] I don’t know how that’s going to scale as we grow larger but for now it’s it’s working pretty.
[22:44] No actually I sounds like a great idea because the people submitting to take a trust they’re going to get an answer right.
[22:48] Yeah there’s an SLA for different priority levels and we kind of broken that out in a kind of map I kind of wanted true that but yeah it’s worked well for us.
[22:58] I think that’s pretty awesome I think that’s that’s a very good idea for other people to turn into another team’s or not write anything where you can have that triage and one person monitoring and so you don’t get the top on the shoulder the hip chatter slack Interruption you doing stuff.
That’s pretty awesome I try to see if I can do some of that here.
Yeah it’s kale it’s always how do you scale things but even if it works now and something else is later I think that’s pretty good.
[23:22] Right that’s the Perpetual engineering question is you know do you know design us the scale now or do I wait until I need to scale it and then then refactor.
[23:30] It’s right you know premature optimization right you know the last thing you put on here is saying no and I think.
Lots of leadership books how to survive Family Life books lots of the stuff is all about the power of saying no and you can’t do it all tell me about how that applies to suffering and management.
[23:50] This is something that.
I had a lot of personal investment in mostly because and this is coming from my CTO he answers I I kind of exude extreme ownership and so anything that crosses my desk and I will fix that.
And so the feedback that I constantly got from him is like you need to say no more like you can’t do everything like delegate you need to delegate more and so that was really a note to myself I don’t know if that applies to everybody but.
I kind of thought okay if somebody’s in the same position as I am like maybe they need this feedback to.
Just saying no more to give yourself the bandwidth to actually do your job because really everything it comes across your desk is not necessarily your job.
[24:37] That’s right and that’s a good point we actually have a problem everywhere I’ve been and even for my managers here one of their quarterly goals has been.
Pick one thing you do and delegate it right pick one thing you do and give it to someone in your team or someone else so that you don’t have to do that one thing anymore right because the part of being a manager I think that.
Associa the new manager is struggling with.
Just that right not keeping every ball in the air and learning to trust and learning to delegate things so that you can do more strategic and let the company rather than doing all of this little.
[25:11] Absolutely yeah.
[25:13] No I mean that’s that’s awesome in the one thing that you want to talk about 2 cuz we were talking just before the show.
You went through I think you did a retrospective red on sort of year you’re 10 years management and you came up with this this blog which is awesome and some of these tips I think of her helpful.
And but you should have went from Individual contributor to manager and then backed individual contributor again.
So tell me a little bit about that thought process that had that happen.
[25:43] Sure so yeah about a year ago Neil and I were sitting down trying to figure out what is our,
career growth ladder or engineering career growth ladder look like,
and yeah we had senior mid-levels jr. Engineering positions we had front of position same same levels and so.
Many of the engineer’s on our team were already at that senior-level so we’re like what is their career path look like.
And the industry standard is kinda to have you know a couple more levels above senior which include a staff engineer maybe senior staff principal architect.
Until we decided that we would go with that kind of ladder for innovation.
And it kind of fit in at the time because we were also releasing another product and so we needed engineering leadership Technica leadership across different products.
Which is kind of the definition of a staff engineer role and so.
Because I had an experience on our existing product and this new product and it seems like a good fit for me to move laterally into this icy new icy slot that we were creating.
Yeah it seemed to work out I was actually really excited about it I had gone to calibrate which is engineering manager conference here in San Francisco last year and.
I’m an engineering manager after engineering manager who had you know talked about their experience of you know doing those pendulum between management and icy and and they seem to move really fluidly between the two roles and.
[27:26] Yeah that got me thinking like I you know I don’t have to commit to do this forever and ever like you know I can move back to IC in the back to management when it’s appropriate when it’s needed,
and the opportunity presented itself Neil asked me if I’d be interested in this position and I jumped at the chance.
Banana for a year now.
[27:50] And you see management again in the future or is it you know you play it by ear.
[27:55] Absolutely I I think I’ve relaxed a lot about the whole management line ever go into management thing I.
I really enjoyed it especially after that first year where I had kind of hit a good Pace a good kind of cadence with with my team and felt comfortable with what I was doing.
I’m in high kind of routine down like I just I really enjoyed it I did miss a building stuff but.
I’m going to do that again so get a little bit of both.
[28:29] And I think one of the things you mention that’s important is he talked about coming up with that engineering ladder right.
Not every company has that dual track engineering ladder will you actually show his you said that comparable right so staff engineer.
Could be comparable to director or principal engineer you know whatever it is and I mean that’s true and I think that’s that by having that now it allows you not only you but other people in your organization or other companies that do it to be able to support that.
Management individual contributor no back and forth because they’re seen on the career progression as.
Different right there different jobs.
Add from the seniority standpoint there equal and it allows people can some companies if you go into it like I said the only career path is to go into management and then you lose an engineer.
And game maybe you can manager maybe not but if then if they feel that they maybe they don’t want to be a management anymore they’re only out is to like go to another company.
I mean I think it’s good it’s pretty Progressive that your company has that sort of ability to go back and forth and to see.
When you go back for management it all should be viewed not as any type of failure right you tried it out you did an awesome job there’s another job that’s power lot of that we’re going to kick ass at that or and and move on.
[29:45] Yeah and I feel very fortunate that our CTO was United of that mindset from the very beginning,
just really espousing the idea that you know management and Engineering I see are parallel tracks and we have both and you do not need to go to management and we have Engineers that have been with us for 6 years and and are still you know.
You know building amazing things and.
And then we also have people who are interested in transitioning to management and and we definitely opportunities for them too so yeah feel very fortunate to be in that kind of situation.
[30:18] That’s awesome are you guys hiring.
[30:19] We are we are.
[30:22] I was it the plug for the come through the gas on here I know that hiring is so hard so you know any top rolls you guys are trying to fill over.
[30:31] Yeah we’re am looking for engineering of all all levels of All Sorts right now we’re really focused on like a data engineering position we’ve got front end we got full stack engineering positions open.
[30:44] Excellent since you’re not a manager anymore you can have a referral bonus so the little Devery one send your resume to Chris Hill he’ll make out like a bandit.
[30:52] I promise that’s not the reason I came on the podcast.
[30:55] So hear the things I want to talk about you is something that today and I think literally like right now it’s just very hot topic right now you talk about psychological safety.
Lots of companies behaving poorly today.
I don’t need to go into some of the specifics here but I think it’s very important not only as a manager right but as an individual contributor that the concept of that that safety has to.
You know it can’t just be a top-down thing has to be peer has to be bought him up right everyone have to participate in creating a psychological safe zone for people.
An end what is that mean to you like why is the psychological safety so important in an organization.
[31:41] When was the developer you know I wanted a kind of safety in order to.
Express my opinions and express a light be able to communicate ideas that may not have been fully vetted to.
Team members and if I didn’t have that kind of safety those ideas may not have gotten expressed and therefore you know the best solution might not have been found.
I definitely see psychological safety being essential to operating at Peak Nino Peak efficiency as a team so.
Yeah it is very timely that we’re talking about this given given what came out this week from Google.
[32:22] Yes exactly right and it doesn’t even think psychological safety is not just about you know gender or orientation or or skin color right it’s.
It’s really just about having an open environment that there’s not one person.
Is dominating or not letting other people speak or just having that feedback about.
[32:46] And I have thought about this a lot this week I mean my blog post was written pretty shortly after the initial study from Google came out I think it was November of 2015 2016 and.
Yeah I kind of threw a couple of small tips there but in light of the news this week you know I’ve been thinking a lot about it and it had become it became clear to me that.
Like a big part of a manager’s position is too you know.
When they’re building an environment that is psychologically safe if they’re trying to build that tea that diverse team they need to like clearly stand up.
Stand up against that kind of behavior like you were saying make sure that everyone’s getting an equal amount of time to speak and make sure they know one dominate like that’s something that a leader needs to do the team can’t self-regulate there or usually doesn’t.
So yeah that’s something that’s been going through my mind quite a bit I mean.
I like my freedom of speech no psychological safety doesn’t give you the freedom to say whatever you want.
So yeah the leader if you want to build a diverse team you can’t really tolerate use that threat or discriminate against you no portion of your teammates.
[34:05] And like one of the things you talked about witches admit when you don’t know something right as a manager you know I think that’s important right and you know your state that.
Because you don’t know anything people might lose respect for you if you you’re blowing smoke and you say you do when you don’t.
[34:23] Yeah and I’ve definitely gotten better about that just from my experience as a manager and I have good role models to their definitely I’ve had good Role Models over the years who Embrace their ignorance as an opportunity to learn.
[34:38] And I like one of the things you talk about to you talk about your hellosign CEO.
And one of the things you talk about is at the end of one and once he’s known for asking you know what feedback do you have for me.
And I think that’s probably one of the most powerful questions you can ask whether it’s a direct report or indirect or anyone in the team right how how is that should of shape some of that culture at hellosign you think it’s had a positive effect.
[35:00] We talk about it all the time yeah it’s it has had a positive effect I think it’s only half the battle though because you really have to build that psychologically safe environment to have you know whoever you’re asking feel comfortable to tell you what they really thinking.
You know a lot of times.
I would say probably like nine times out of 10 maybe eight times out of 10 when I asked that question I get kind of lost you know it’s so so yeah I definitely you need to continue like actively Foster.
You know the exchange of honest dialogue with people so yeah it’s not just about asking question although that’s definitely the first step.
[35:39] What are the things to I brought in some external coaching to for some of our managers here.
And I said one way to get more maybe feedback is to have the less open-ended question and do you have any and say.
Give me your feedback on this decision.
Right or give me my feedback on you know something I just did and then it’s hard for someone to say no because it’s very it’s not like do you and it’s like no but it’s.
What was your feedback on this you can’t say no is easy so it is going to put some in the mindset of getting maybe a more valid answer.
[36:17] I love that I’m going to start using that right away.
How am I doing on this car Castle.
[36:23] Right this is awesome so you mentioned it’s it’s important what what other things or tips you have to help create that safe environment.
[36:34] That’s a good question I probably have to revisit my block list.
[36:40] I mean on an everyday you know standpoint you know you’re in the office your developer to me what makes you feel safe.
[36:45] Hertz Ashley can I load that up just to take a.
[36:54] Absolutely do you know where.
[36:54] Because I do remember I talked about it like saying I don’t know I’m asking for feedback.
[37:08] I can hit all this out right so it’ll be a question and then you come back with a spoon.
[37:13] I wrote this in December 2015 so it’s been a while.
[37:24] It’s a beauty of not live.
[37:31] So you’re you’re asking what other tips I have for cultivating psychological safety okay yeah.
[37:42] So as a leader I think that it’s it’s really important to.
Acknowledge effort and I do kind of talk about this in the blog post and it and it did get a little bit of in a back-and-forth with people who didn’t necessarily agree with us but.
It you know on our team even if.
Some big features released that you know suddenly has as a big problem big bugs found with it you know.
And one of your developers stays up till 2 in the morning fixing it.
The result may not have been ideal but you’ve got to celebrate that wow you really went above and beyond here.
And that’s something that we do routinely it’s it’s something that you know we we definitely focus on.
I’m finding causes and or identifying causes and preventing you know those sorts of things from happening in the future we hold blameless post-mortems where we talk about you know what are the action items we can do to prevent this in the future.
Get ownership on those interest just run with it and that’s something that I definitely credit our founders with kind of starting.
And I just deleted celebrating effort that definitely create a space in which people feel like they can fail and it’s okay.
I mean obviously you really want to celebrate successes to so yeah it kind of goes both ways there.
[39:12] Awesome and you know what other things we didn’t mention today that you know you wanted to come to share kind with the audience anything specific around leadership any final notes.
[39:28] One I think it’s important one of these you mention that I do want to reiterate as well is it’s okay ready to go to go become an individual contributor going to management and then go back.
[39:41] Yeah that’s a really good point.
[39:42] And I think that is in to feel okay doing that and to not stay in a role that you don’t like or maybe isn’t suited for you because like most people here that I had not even experience so.
Trying it out you know you should be celebrated and then even going back to feeling neck at this company I can I can contribute more effectively.
As a principal engineer is a staff engineer.
[40:03] Absolutely yeah that is one thing that I wished I’d known up front is that I could make that transition I could go back and forth it wouldn’t you know.
Did I think I would probably looking back I wish I could have relaxed a little bit more and Trust in myself a little bit more and.
Yeah there was definitely a couple of points where I was a little bit frantic and like asking my teammates like how can I provide value to you.
They’re like what are you talking about like don’t you see all of the amazing stuff that you help us do and I’m like no like I feel like I’m not doing anything so.
And say I wish I could go back to myself and be like dude just chill like it’s okay you know it just focus on the team and.
Yeah it’s it’s been a lot of fun I’m really happy that I went through that and I would definitely do it again.
[40:57] Awesome Chris what’s the best way for listeners to get a hold of you.
[41:02] That’s way is probably either through email or or LinkedIn or Twitter which I’ve given you.
[41:10] Okay great so definitely I will put those also in the show notes so that’s awesome I’m going to thank you Chris for coming by this afternoon really great enjoy the conversation thank you very much.