Sid Sijbrandij: How I Founded GitLab; Remote Work vs In-Person; CEO Coaches | 20VC

1. 0:00 – 15:00

   (beeping) Three, two, one,…

   1. SSSid Sijbrandij0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination.

   2. HSHarry Stebbings0:12

      Sid, this is such a joy to do. It's been so long since our last discussion. I was trying to think. It's like three or four years. I mean, I was young when we last spoke. But thank you so much for joining me again today, Sid.

   3. SSSid Sijbrandij0:23

      Yeah, it's a pleasure. It feels on one hand like yesterday, and on the other hand, so much has happened since. So thanks-

   4. HSHarry Stebbings0:29

      I mean-

   5. SSSid Sijbrandij0:29

      ... for having me back.

   6. HSHarry Stebbings0:30

      Not at all, but so much has happened. But I, I do want to start, and for those that missed our last episode, you know, GitLab today, public company, incredible success story. Would love to just provide some context and go back to the beginning. What was that founding moment and how did it all start? In a very succinct two to three minutes.

   7. SSSid Sijbrandij0:49

      Yeah. It started when I saw, uh, GitLab, which was created by my co-founder Dmitri. Um, he started it because he wanted to be... have a better way of collaborating at work. And he thought it made so much sense to make that open source, and I thought so too. So GitLab is a DevOps platform, which means you can do anything from planning what you're gonna build software-wise to building it, testing it, making it secure, rolling it out, monitoring it, and improving it. And he thought that made so much sense to collaborate, and in the first year, 300 people joined. Today, we have hundreds of people joining every month to make it better. GitLab is being used by millions of people. This deserves more than just an open source project where everyone is just working for the love of it. This needs full-time people, and today GitLab is over 1,500 people.

   8. HSHarry Stebbings1:48

      I mean, it, it's incredible to see and also kind of incredible to see the different stories actually of the employees. You know, I know many of your team members and seeing them talk about bluntly how they live, which is what we're gonna come on to next, which is, you know, you've always been a remote first company, many, many years ahead of everyone else who's now doing it. And so I want to hone in here a little bit, and I actually spoke to Darren, your head of remote before the show, and he said, "First of all," you know, a lot of people ask, "Well, how do you do it?" Ask instead why, because as I said, it was a very contrarian thing that you did many years ago. So Darren asked bluntly, "It seems you're wired pretty differently with remote being the best solution inherently to you. What shaped this? Was it conviction? Was it personal experiences? Why did you always feel it was right?"

   9. SSSid Sijbrandij2:34

      We started off as a remote company. Um, I had... I hired people, but well, the first person I hired was in... Uh, I was in the Netherlands, and the first person was Martin in Serbia. And then we hired Dmitri in Ukraine, and it, it kept going like that. And then even if I hired Dutch people, they, they would come to my house and we would co-work for a few days, and then they would just work from wherever they were. So it organically evolved like that. And then people were skeptical. So we said, "Look, if it... if it stops scaling, we'll stop doing it." But in fact, remote works better the bigger you are. Like if you're seven people, it's probably better to be in a room together if that's practical. If you're 1,500 people, what's the... what's the advantage? You can't be in the same room anymore. You can hardly be in the same building. So remote scales a lot better and because people were skeptical of it, we invested a lot in the things you need to do to be remote. Every company during the pandemic discovered, "Hey, we can work remote." But what they are not intentional about is facilitating informal communication, because that takes more time and effort. It takes a lot less time and effort and money than having an office building. But you still need to be very intentional about that.

   10. HSHarry Stebbings3:54

       Respectfully then, what do you do to faci... to facilitate that informal communication and bring that culture to the scale of remote that you have?

   11. SSSid Sijbrandij4:05

       We do a ton and we give a ton of examples, but one of the things we do is coffee chats, and it's kind of the water cooler chat maybe. It's very normal at GitLab to plan 25 minutes on someone's calendar and just call it a coffee chat. You don't need an agenda. You don't necessarily need to talk about work. We normalize that. If you onboard at GitLab, we make you do five so that it's very normal. You don't have to do them. Not everyone wants to hang around the water cooler, but at least make it normal to do things like that. And there's 20 other examples on the... that we list.

   12. HSHarry Stebbings4:40

       What, what other ones have you found really move the needle? And also have you find any that didn't actually work or people found quite annoying? I'm just interested.

   13. SSSid Sijbrandij4:48

       There's, there's lots of different ones. I, I think, um, a hangout as a team every week, um, is very beneficial. We also... we believe in, in being together in person. We, we fly everyone in, uh, before and hopefully after the pandemic to one location to just hang out for a week together. That, that can be very beneficial. Um, I think what we've always done is make it optional. It's not for everyone. Some people are just very busy, they just want to get their work done and, and they're fine. So the, the demand for it really varies, uh, according to who someone is and what phase they are in their life.

   14. HSHarry Stebbings5:30

       Totally get you and I, I completely understand that. I, I do want to ask, you know, uh, you wrote the most incredible, um, kind of remote guide that so many startups use as their centerpiece today, especially, uh, also now for kind of larger incumbents who are tr- moving, transitioning towards remote work. Well, and this was Darren again, so I have to give him credit. What do you think are one or two things in there that will require the most effort to implement for those wanting to make the transition?

   15. SSSid Sijbrandij5:57

       I think this informal communication is the most important thing.... we've talked to a ton of companies and most of them spent more time on deciding when to get back to the office than how to make remote work while they're not in the office. Also, I think it's a pipe dream that we're gonna go back to completely being in the office. Some people are gonna be remote. So focus more time on making that work. When people say they long back to the office, they don't mean the furniture. When companies open back their offices, less than 10% of the people go back. They are longing for that informal communication. It's very natural for your Zoom calls to start on time, to end on time. You need to be intentional about creating time and space to learn more about each other, to build trust. That's essential and that's what people are longing for and that's what has been missing in a lot of companies during the pandemic.

   16. HSHarry Stebbings6:49

       I, I, I totally agree with you in terms of that being missing. I also love that in terms of kind of how you see the future there. I spoke to Dave at, uh, Google Ventures, or GV, beforehand and he said, "Really dig in on this one because, you know, a lot of startups are thinking about the next 10 years." When you look towards the next 10, 20 years of scaling startups and org design, what's your view on the future of work, uh, in terms of kind of remote, partial, full, and how do you think about that? That's from Dave.

   17. SSSid Sijbrandij7:18

       I think the future of work, I see a lot of startups are s- are being all remote, they don't even have an office. So that w- that's gonna happen and that's gonna happen more and more often. Now, the legacy companies who are gonna go full, like co-located, that's gonna work as well. We know that works from, from before the pandemic. And then there's hybrid, and I think there's a type of hybrid that works and a type of hybrid that doesn't work. The type of hybrid that works is you come into the office some days. And I think companies are gonna find out that it should be the same day so everyone's at the office at the same time. The hybrid that doesn't work is some people are at the office and some people are remote. We think the most talented people in those companies that work remote will leave for a company that's all remote because they wanna be on the same level as everybody else.

   18. HSHarry Stebbings8:08

       Yeah. No, I, I totally agree in terms of being on the same level as everyone else. If we think about taking your level up a gear, obviously your level of remote is incredible prowess, the OG of remote work. Um, but Darren said, "Ask how we can still further improve." So when you look at yourself today, what more do you think you can do to improve your level and GitLab's level of remote work?

   19. SSSid Sijbrandij8:33

       The hardest thing about remote is time zones. And to overcome time zones, you need to work asynchronously, but that's very, very hard. If I look at my day, I spend almost all my day in calls. If I look at the, uh, eGroup at GitLab, my reports and all of them are located in the US. So where we can improve is to work more async and to have an even bigger, uh, geographic distribution. We have people in over 60 countries and I would love for, uh, the eGroup and, uh, uh, our board to reflect that as well.

   20. HSHarry Stebbings9:09

       Can I ask how many of your calls on reflection do you think are necessary? And what I mean by that is how many of them could be done through async note sharing, comment sharing on Google Docs, Notion, you name the tool that you want, but how much could actually be done without the call do you think, percentage wise?

   21. SSSid Sijbrandij9:28

       At GitLab, you're not allowed to present in meetings. So I had two meetings before this one. Three, actually. One was with my parents. You shouldn't call that a meeting.

   22. HSHarry Stebbings9:39

       (laughs)

   23. SSSid Sijbrandij9:39

       That was just a call, but I, I had family ca- uh, family calls, uh, throughout my, my morning and I just planned them in so that work doesn't schedule over them. I had, we had a group conversation about our brand, about marketing, uh, uh, our brand. And there was a presentation, there was something you could see, but it's not happening in the call. In the call, it's just Q&A because that's the part that's harder to do, uh, and that you need a synchronous meeting for. The other thing was a prep for this call. Um, it was a 10-minute prep and there's a really good document about like how I should prepare and all the questions you might ask and everything else. And I was like, "Well, why is this a synchronous call? Why not instead of a synchronous call, we do it as async? I promise to read the doc and leave my notes and you get back to Harry a couple of days before and share the notes I already took? Because, uh, some of the questions you might ask today, I send a link. Wouldn't it be fun for you to ha- at least have the opportunity to read that link?" So let's try, like if, if I gotta b- impress anybody about how good we are at remote, it's Harry.

   24. HSHarry Stebbings10:53

       Right. (laughs)

   25. SSSid Sijbrandij10:53

       So let's try to, let's try to sh- show them that at least we, we try to do our very best working asynchronous.

   26. HSHarry Stebbings11:02

       That, listen, I, I, I totally agree with you. I often look at most of my day and I'm like, "Fuck, that could have been done over email and, you know, document sharing." So I'm totally with you there. Uh, I, I do wanna ask, you know, when you think about the evolution of the company, you know, we've got many, many mutual friends. We mentioned Dave at, at Google Ventures, uh, just there. Um, he said, "It's been incredible to see you evolve as a leader," specifically. When you kind of reflect on your own style of leadership, I guess first, how would you describe your style of leadership? And then second, how has it changed over time, as I'm sure it has done?

   27. SSSid Sijbrandij11:37

       Yeah. So the top three values at GitLab are results, iteration, and transparency. So I hope, I strive to be a leader who's transparent, who iterates, so always looking for the smaller thing that could be done faster. And the company is all about results and, and making decisions based on, on results. And as for the evolution, I've learned to delegate more, I've learned to be more patient, and I've learned to give more context so that people could make a decision on their own.

   28. HSHarry Stebbings12:10

       ... can I ask, in terms of the transparency, are there any limits to transparency? Are there any boundaries? Is it salaries? Is it... You know, I often say that startups never involve team in M&A discussions or progress because it's just- it's unhelpful and it's unproductive. Don't actually say about fundraising. It reduces morale if they know that it's dragging on. There is a limit to transparency, I- I always say. How do you feel about that?

   29. SSSid Sijbrandij12:36

       Because we're transparent by default, we have the longest list of things that aren't transparent. So if you Google GitLab communication, you'll find a long list, I think it's over 17 items, of things that aren't transparent. And that includes salaries, that includes M&A. It doesn't include fundraising, but it really depends on your market and how you're going, uh, with that. It- it was a stretch and we had a fundraising Slack channel where we keep- kept people updated. But we knew we were an attractive company and the- the market was good. So, it- it- I think you- you have to make that decision, but it's certainly... That- that is a very hard thing to do because as that- (laughs) the subject in that channel said, it's gonna be a roller coaster and there're g- there's gonna be lots of nos, but we only need one yes.

   30. HSHarry Stebbings13:23

       You mentioned also iteration there. Eh, another commonality in, I know all of our friends who I spoke to, said about your rate and desire for learning being unparalleled. And so if we- if we go to that, how do you think about getting as much feedback as possible from your team, customers, investors? And then how do you determine the feedback to accept versus reject?
2. 15:00 – 30:00

   Can I ask, in…

   1. SSSid Sijbrandij15:00

      I- I would take that more serious than someone on Twitter that I don't know. And also, what's the specialty of the source? Is that person really good in X, Y, Z that they're giving feedback about or not?

   2. HSHarry Stebbings15:12

      Can I ask, in terms of like the feedback, you said there about kind of rewarding people for it. How- how do you make people physically feel, you know, you are incredibly personable, humble, great- great bloke (laughs) as we'd say in the UK, Sid (laughs) . Um, but you're still the CEO and people will inherently just be a little bit more intimidated, especially if they're kind of lowering the company transparently. How do you make it a environment of cult- and a culture, of like safety and security where they can say, "Sid, I didn't like the way that you actually said that and it made me feel uncomfortable." How does one create that environment where they can say that?

   3. SSSid Sijbrandij15:51

      I think situations where you're giving feedback in a group setting are the most important because there people can see what happens. Um, also, it's really important that people never get in trouble for their feedback. So, I think in group settings when someone has feedback, being thankful for it, and also like being humble about... Sometimes you kind of know, like this morning when I gave the feedback, "Hey, we should share the doc with Harry up front." I was just... I w- I was just starting my day, I wasn't at my best, but that's no excuse for delivering that feedback in a way that w- that wasn't- that wasn't pleasant and that wasn't constructive. So, I- I did a bit of damage control. I said, "Look, um, you didn't nothing wrong," but still, that- that wasn't good. So, some- sometimes you know when, um... If you criticize yourself from time to time, it's easier for other people to do the same.

   4. HSHarry Stebbings16:55

      I think you're a bit hard on yourself, Sid (laughs) . I think that was-

   5. SSSid Sijbrandij16:58

      You weren't in the cohort, Harry.

   6. HSHarry Stebbings17:00

      (laughs) Okay. This is true, to be fair, but I can't imagine you getting angry, you're always so calm and level-headed. Um, uh, but you know, w- we said about kind of async and we said about feedback, eh, you know, a lot of your investors said about this written culture that you have very much embedded within GitLab. Uh, first, what does a written culture really mean and feel like to you? And I guess, what are the biggest pros and cons of having that written culture so central?

   7. SSSid Sijbrandij17:27

      Yeah. About the first thing, maybe I'm not angry, but I do care a lot. And if it's a subject I care about a lot, it- it's sometimes I- I make the point bigger than it- it should be. And then a written culture means you write things down.

   8. HSHarry Stebbings17:41

      Can I- sorry, can I just- can I just interrupt?

   9. SSSid Sijbrandij17:43

      Sure.

   10. HSHarry Stebbings17:43

       Sorry (?) How do you temper yourself too? Because I have a situation today and I'm asking your advice here, where it's exactly the same as you. I- I just care intensely about my business like you do yours. And if I feel like someone is not helping me get to where we should be, I get very angry. Um, especially if it's born out of laziness or lack of care. How do you temper your emotion as a leader? Because actually it's not helpful getting angry.

   11. SSSid Sijbrandij18:16

       ... it's, it's hard and what we try to do at GitLab, which is super hard, but, like, don't question people's intentions. So, I agree that some people are... have a harder time motivating themselves, but I think laziness is almost a shortcut that's, that's too easy. Like, what's going on in their life? That might not be, that might not be an excuse to do it, but I think most of the times when I'm lazy, it's because I have too over high bar for the output and the end result and I procrastinate and try not to do it. Um, so maybe it's something like that. Um, we're all humans. We all... Like, I, I, I, I might, I might be... Yeah, I'm trying to be as level-headed as I can and I think I do a good job. That, that doesn't mean you're, you're always at your best and nobody is. And I think it's kind of fun to work with humans instead of robots and to vary your style. One of the things I, I like most is the situ- situational leadership, uh, theory and strategy where you vary your style based on what happens. I've, um, made a blog post in, uh, November with 19 factors I can consider and I sometimes do consider when, when to delegate something. And that's, that's kind of the name of the game, like, the who's on the other side and, and what sh- how should you vary your style and I think that makes being a leader more interesting. And, uh, and it's... I'm never gonna master it, but I'm, I'm, I'm... It's fun getting better at it.

   12. HSHarry Stebbings20:06

       Uh, listen, I, I, I totally agree with you. In terms of kind of transitioning the styles that we mentioned about the written culture, I would lo- love to ask, what does that written culture mean to you? 'Cause it is a big change in the style of leadership and how companies

   13. SSSid Sijbrandij20:18

       So, we have a strong written culture and it shows in our handbook of over 2,000 pages-

   14. HSHarry Stebbings20:30

       Perfect.

   15. SSSid Sijbrandij20:30

       ... where we detail how we work. Um, the, the enormous benefit is that there's less synchronous time needed. Like, you're less likely to be stuck and need to ask something to someone before you can continue. I think one of the drawbacks of writing is that it can be time-consuming, especially if something needs to happen fast and you don't know how much context the other person has. 'Cause now you need to kind of write down everything the other person could possibly not know, and that takes a lot of time. If, if you have more time, you just send something short and they can ask a question. If you know the other person has the context, you can have a shorter text message like you would have with, uh, a partner, uh, both in business and, and in personal life. So, um, I, I, I think there's a benefit to it, but if something is really important and has to happen really fast and it includes a wide group where you don't... where not everyone has the context, I think synchronous communication is better.

   16. HSHarry Stebbings21:34

       I, I totally agree with you in terms of that. Uh, I do want to ask, in terms of... You know, we, we mentioned Dave earlier. He mentioned, uh, how important, uh, you... a role you played in terms of mentoring some of his companies and working with companies that he's worked with. I'm intrigued. How do you think about the role of mentorship today as a leader? And I guess, what would you advise young people, say, when it comes to mentors?

   17. SSSid Sijbrandij21:58

       Mentorship is super important. I've been helped by a ton of people in my career and I, I really enjoy mentoring kind of both, uh, startup companies and, and, um, kind of promising people at GitLab. Um, I think what's really imp-... What I see sometimes is that people reach out and ask whether you want to be their mentor, and I think that's, that's unlikely to be a yes, uh, for me, but I think also from other people. I think you wanna kind of... You wanna start small. Iterate, maybe. Um, you, you wanna reach out and say, "Look, I got this problem. This is why it's super important for me to solve it. This is what I think about it. This is what I would do if I went and talked to you. This is why I think you're, like, the most qualified person in the world to, to help me with that. C- could y- could we hop on a 10-minute call to have a back and forth?" I think-

   18. HSHarry Stebbings22:56

       Mm-hmm.

   19. SSSid Sijbrandij22:56

       ... that's... You're much more likely to find your mentor that way than just a cold reach-out.

   20. HSHarry Stebbings23:02

       Uh, listen, I totally agree with you. Can I ask you, who are your mentors today? And if you have one or two big takeaways that you really think on from them?

   21. SSSid Sijbrandij23:13

       There's a, there's a ton of people. I think the, the most important people are... have been my, my CEO coaches and, and also the board members. Now, board members are not mentors per se. They're, they're your boss, which is very different. But still, there's a... an enormous amount of things you can learn. And for example, Godfrey Sullivan, our lead independent, he helps me with the situational leadership, like varying my style. Um, I think with the CEO coaches, um, right now it's Marissa and, uh, before it was Jon Hamm. And Jon Hamm, his most impactful statement was when our quarter was looking really, really bad. So, this is years ago. We were gonna miss-

   22. HSHarry Stebbings23:58

       Mm-hmm.

   23. SSSid Sijbrandij23:59

       ... the quarter by 30% and I thought, "Oh my goodness, I'm gonna get fired." I was like a deer in the headlights.

   24. HSHarry Stebbings24:07

       Right.

   25. SSSid Sijbrandij24:07

       And, uh, Jon said, "Look, first of all, you're not, you're not gonna get fired. Second of all, they know startup is up and down."... but they want you to completely understand the problem and have a plan on how to deal with it. And that sounds trite. That sounds so simple, but that was so useful, and for the next, I had two weeks until the board meeting, I learned everything about the problem and it was with, uh, our sales cycle and deals getting stuck and things like that. And I started off the board meeting with a half an hour presentation with everything that was wrong and everything we were gonna do about it, and the only response was, uh, from Philly, "Sid, don't do any crazy things." He meant don't close any deals on kind of bad terms in order to make the quarter, which we never have. Um, but they saw, they, they saw I understood the problem and what we were gonna do about it.

   26. HSHarry Stebbings25:01

       Uh, listen, I, I absolutely love that. Can I ask in terms of CEO coaches, how do you work with them? You mentioned, you know, John there and Marissa. Uh, how do you work with them? How long do you stay with each one for? Wha- how do you advise founders and CEOs who are contemplating, "Do I get a CEO coach? Do I not get one? I've heard that they're valuable, but is it really for me?" How do you think about that?

   27. SSSid Sijbrandij25:24

       If you're the CEO of a fast-growing company, I totally recommend it. I think you, y- the nice thing is, you, you get the best possible CEO co- CEO coach who will have you. And just like everything in all the relationships, you'll, you'll have to work for this one. Uh, so it's, it's, it's kind of a two-way recruiting process. Uh, so you find out by other people who, who's, who the good coaches are. Uh, they all are busy. They will never have time, so you gotta, you gotta make it interesting to them to take you on as a coachee, so you gotta convince them that you're a great person at a great and a promising company. And then, typically, I think a few years, it, uh, you stay with them. It depends on what stage your company's at. It's important that, uh, the coach has seen that stage of company before. And I think after you outgrow a coach, you, you, you move on to the next one. Also, there's, you're, there's a, there's kind of they're sharing their life knowledge, and at, at some point, you, you kind of, you've learned a lot of what, what you're gonna learn from them.

   28. HSHarry Stebbings26:36

       Yeah. No, listen, I totally agree. How do you know when you've reached that asymptote of information that you've learned from them? And what I mean by that is, how do you know when the values plateaued and actually it may be time to get a new coach? Nothing on them, but just the time is right. Is there, is there a signal or a sign?

   29. SSSid Sijbrandij26:54

       Th- th- this is not an exact science, but heh, it's, it's, it's leveling off, and you start hearing the same things more and more.

   30. HSHarry Stebbings27:02

       Yeah. No, I totally get it. I think it's the same for my personal therapist, but I, I think that's a different story, Sid. Uh... (laughs)
3. 30:00 – 41:11

   I think one thing…

   1. HSHarry Stebbings30:00

      and then what have been some lessons in terms of what you can do to be the best board member? And, and also, like, help me. I'm on boards. What can I do to be the best board member?

   2. SSSid Sijbrandij30:09

      I think one thing I was really afraid of is that, uh, I, I'd put myself too much in the operator's seat. You see that with kind of, especially with current CEOs. Like, I'm in execution mode most of the day. Like, uh, making, making decisions, uh, and, and-... planning activities and giving suggestions. As a board member, you should really only be asking questions and getting informed, and I'm very cautious of doing the right thing there. And so far, it's, it's going pretty decent, although we should ask Dawood, not me.

   3. HSHarry Stebbings30:43

      (laughs)

   4. SSSid Sijbrandij30:45

      Um, and then great board members are, in my view, very knowledgeable, very high signal to noise, um, they don't wanna show off in a board meeting. They g- don't, don't have to impress other people with how marvelous they are. Everyone in the board knows kind of this is a good board and everyone is marvelous. Uh, they don't need to talk to get that confirmation. They're very certain of themselves. And they, they have... They tend to have a specialty. Like, they're, they, they tend to be really good in a few things, and, and those specialties should augment each other.

   5. HSHarry Stebbings31:20

      Can I ask you for help and advice, Sid? When you have a challenging situation and a board member has feedback which is helpful, but it's direct and it's about a tough problem that the company is facing, I'm always challenged by, should I say to you, "Sid, can we just have five minutes at the end and me and you will discuss it?" Or should I bring it up with you head on in the board meeting and bluntly challenge you on it, not in a horrible way, but challenge you in front of everyone else? Because then you do get the benefit of the crowd and their opinion, but you could also seem like you're confronting the CEO in a more afflicting situation. What's the right answer there?

   6. SSSid Sijbrandij31:59

      I think... Is it, is it a company problem or is it a CEO problem? So if it's-

   7. HSHarry Stebbings32:04

      It's a company problem. It's a company problem. Strategy around go-to-market.

   8. SSSid Sijbrandij32:07

      No, no, no. Strate- strategy is wrong. I think it's... That's exactly what a board meeting should be about, so you should bring it up in the board meeting. Um, I think what's really important is that a CEO never has to say to a company, "Hey, the board wants to do X, Y, Z." So as a CEO, you should be very cautious of never saying that. Either you disagree with the board member, just fight it out, or you accept it and now it's your opinion. But it... The board is not running the company, and if you... At GitLab, we allow a ton of people in board meetings, and, uh, that's a, that's a risk that you have to manage. Um, so when you call out that the strategy is kind of going sideways, make sure that you don't tell them what to do. Don't tell them, "Change the strategy to X, Y, Z." You, you, you're just there to ask questions. But the questions can be tough and challenging, and you can, you can say, like, "Look, that's, that's not a very convincing, uh, data point that you're basing that strategy on."

   9. HSHarry Stebbings33:11

      I- I'm too interested. You said the board meetings are a little bit larger than normal. Uh, how do you structure who gets invited to the board meeting, how long the board meetings are? Just the formalities. How do you actually structure them? I'm interested.

   10. SSSid Sijbrandij33:23

       So, um, we have a great page on, on board meetings, so if you Google GitLab board meetings, you'll find more information. Uh, those of us are, uh, one and a half hours open session and then about 45 minutes closed session. So, um, you... It's not five minutes you should do a closed session. You should do it for 45 minutes, and then about 30 should be with the, with the CEO, and then 15 without the CEO to eval- evaluate her performance. Um, and it's... We've, we've started something else. We do kind of a, a k- a... I don't know. We don't call it a kickoff of the board meeting, but we do a small closed session before the board meeting, and it's to give the board context on... Some additional context on like, what, what do we want to get out of this? What are things do we... To really pay attention to? What do we really want your opinion on? And also, like, who to praise in the board meeting. Like, who are the "my reports" who will be there who did an outstanding job and, and should get some praise from the board for that?

   11. HSHarry Stebbings34:31

       Yeah. No, I, I, I totally agree with you, especially on the praise element. We've mentioned kind of board meetings, board members. Final one before the quickfire, but, um, a lot of your cap table told me how, um, rigorous and stringent you were around investor selection, which is always a great thing to be.

   12. SSSid Sijbrandij34:48

       (laughs)

   13. HSHarry Stebbings34:48

       Um, but my question to you on the back of that was, when you think through the cap table that you've assembled, which is incredible, why did you choose the people you did? Like, how do you base your investor selection criteria for you?

   14. SSSid Sijbrandij35:02

       So this is now in our past. We're a public company, and so-

   15. HSHarry Stebbings35:05

       Yeah.

   16. SSSid Sijbrandij35:05

       ... the last time we got to, uh, select was, uh, at our IPO. And, look, you, you select firms with a good reputation that they're constructive, and then you select people. Uh, frequently, they're, they're gonna be your new board member, the lead investor in the round. So you like people who you could have a great board meeting with. And what I did, for example, in our B round, I kind of had... Calling it a mock board meeting is too far, but I went through our strategy and kind of, um, waited for them to kind of... Waited. Well, we discussed and asked them to add value. And, and then what you get back help- you select the, the person who, who can contribute the most.

   17. HSHarry Stebbings35:50

       Yeah. No, listen, I, I'm totally with you, especially in terms of focusing on the person and that relationship is central. I do want to move into my favorite, Sid. You know the drill. Uh, I say a short statement, you give me your immediate thoughts. Does that sound okay?

   18. SSSid Sijbrandij36:02

       Yes.

   19. HSHarry Stebbings36:03

       Okay. So, uh, I'm terrified with this one, 'cause I'm sure you read endlessly. But what's the favorite book and why?

   20. SSSid Sijbrandij36:10

       Uh, High Output Management, and I love how kind of situational leadership is kind of woven into that.

   21. HSHarry Stebbings36:16

       Tell me, what is the hardest element of your role with GitLab today?

   22. SSSid Sijbrandij36:21

       We're a functional company, so cross-functional initiatives are the hard- hardest thing to do well.

   23. HSHarry Stebbings36:27

       Why is that?

   24. SSSid Sijbrandij36:30

       ... because it's always hard to cross organizational boundaries, so y- you can select. Y- you have two options. Like, you can... Three options. You can structure your company according to functions, and then cross-functional things will be hard; you can structure your company across projects, and then career development will be hard; or you can have a matrix organization, and then your whole life will be hard.

   25. HSHarry Stebbings36:54

       (laughs) Oh, dear, I love that. Um, what is the one thing (laughs) about GitLab that most people do not understand, Sid?

   26. SSSid Sijbrandij37:03

       That DIY DevOps is dead. Like, the, the area of selecting 10 besting class solutions for DevOps and then having custom integrations between them that you maintain, that is no longer working. It's both not leading to a good outcome, and it's way too much effort.

   27. HSHarry Stebbings37:21

       Uh, uh, interesting to change of topic here, what does the fu- uh, I got, obviously a little birdie told me about this one. What does the future of cities look like to you?

   28. SSSid Sijbrandij37:31

       I think there will be more cities. They will be more differentiated and opinionated, and they will be more welcoming. They will have a recruiting department.

   29. HSHarry Stebbings37:40

       T- uh, I think Francis Suarez in Miami is doing a good job on that one. Um, uh, I do have to ask, uh, how do you think through your personal investments today, Sid?

   30. SSSid Sijbrandij37:50

       Well, considering what this, uh, podcast is about, um, I started Open Core Ventures together with Betty as, uh, COO, and we, uh, we create companies around open source projects. So, I think that, uh, returns in venture are moving earlier and earlier, and we're investing before they're a company because we're creating it.

Episode duration: 41:16