Mar 20, 2022 · 41m · news
Sid Sijbrandij: How I Founded GitLab; Remote Work vs In-Person; CEO Coaches | 20VC · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Twenty Minute VC, host Harry Stebbings interviews GitLab co-founder and CEO Sid Sijbrandij to discuss the company's growth, its pioneering remote-first methodologies, and critical lessons in executive leadership and board management.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 28.9% of the talking time here. How this is scored →
Harry as informed peer 3.4 Guest teaching 5.0 Guest disagreement 1.9 Harry pushing back 2.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:16 Sid rejects the laziness framing
Sid directly counters Harry's view that employee underperformance stems from laziness, calling the term a shortcut and reinterpreting slow output as procrastination caused by overly high standards.
Hardest push from Harry ▶ 31:20 Harry presses on confronting CEOs in board meetingsHarry pushes Sid on board dynamics, asking directly whether a board member should challenge a CEO on strategy publicly in front of the board or pull them aside privately.
Biggest teaching moment ▶ 12:36 Sid explains default transparency mechanicsSid educates Harry on organizational design, explaining that being transparent by default actually requires maintaining an explicit, categorized list of non-transparent items.
Harry holds his own ▶ 12:10 Harry asserts boundaries on transparency in M&A and fundraisingHarry demonstrates strong startup expertise by presenting a detailed case on why transparency must be limited during M&A and fundraising to avoid tanking team morale.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Founding Story of GitLab | 3 | 4 | 1 | 2 | Harry sets up the founding story and asks about GitLab's early remote-first decision, citing insights from GitLab's Head of Remote and GV contacts. Sid educates Harry on why remote work scales better with thousands of employees than in small offices and explains why certain hybrid models fail. The tone is highly collaborative and respectful. | |
| Improving Remote Work through Async Communication | 3 | 5 | 2 | 1 | Sid explains how GitLab uses asynchronous communication to bridge timezones, using his team's interview prep for Harry as a live example of replacing unnecessary calls with shared docs. Harry readily agrees with Sid's point that most daily meetings could be conducted async. | |
| Leadership Values, Transparency, and Constructive Feedback | 5 | 5 | 2 | 4 | Harry offers a firm viewpoint on the limits of transparency, asserting that startups should never share M&A or fundraising details due to morale risks. Sid reframes the argument by explaining that default transparency requires an explicit list of non-transparent items, educating Harry on GitLab's explicit handbook policy. | |
| Managing Emotions and Situational Leadership | 2 | 5 | 3 | 3 | Harry asks Sid for personal advice on managing emotional frustration when employees underperform due to perceived laziness. Sid gently rejects Harry's premise, arguing that calling employees lazy is an oversimplified shortcut, and teaches the principles of situational leadership. | |
| Written Culture and the Art of Mentorship | 3 | 5 | 2 | 1 | Sid breaks down the trade-offs of written culture and explains how young founders should seek mentorship. He dispels the common habit of cold-requesting a mentor, laying out a structured 10-minute targeted reach-out process instead. | |
| Mentors and CEO Coaching Lessons | 3 | 5 | 1 | 2 | Sid shares stories about his CEO coaches and board members, detailing how coach John Hamm helped him navigate a 30 percent quarterly revenue miss. Harry asks practical operational questions on identifying when a CEO coach's value has plateaued. | |
| Playing the Role of a Board Member | 5 | 6 | 2 | 4 | Harry challenges Sid with a concrete dilemma on whether board members should confront a CEO publicly during a meeting or privately in a sidebar. Sid educates Harry on board governance boundaries, emphasizing that strategy issues are company problems meant for open board discussion. | |
| Quickfire Round: DIY DevOps, Cities, and Open Core Ventures | 3 | 5 | 2 | 1 | In the quickfire round, Sid decisively declares that DIY DevOps is dead, outlines his venture model Open Core Ventures, and explains why he uses CEO shadow observers to rate his meeting positivity. |
Statements from this episode (24)
Sid Sijbrandij: Remote work scales better as a company grows larger
“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 1500 people, what's the advantage? You can't be in the same room anymore. You can hardly be in the same…”
Sid Sijbrandij: Returning completely to in-office work is a pipe dream
“Also, I think it's a pipe dream that we're going to go back to completely being in the office. Some people are going to be remote. So focus more time on making that work.”
Sid Sijbrandij: Less than 10% of workers return when offices reopen
“When companies open back their offices, less than 10% of the people go back. They are longing for that informal communication.”
Sid Sijbrandij: Top remote talent at hybrid companies will leave for all-remote
“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 want to be on the same level as everybody el…”
Sid Sijbrandij: Time zones are the biggest obstacle to remote work
“The hardest thing about remote is time zones, and to overcome time zones, you need to work asynchronously, but that's very, very hard.”
Sid Sijbrandij: All GitLab executive group members reside in the US
“If I look at the e-group at GitLab, my reports, and all of them are located in the US.”
Sid Sijbrandij: GitLab strictly bans presentations during internal company meetings
“At GitLab, you're not allowed to present in meetings.”
Sid Sijbrandij: GitLab lists over 17 transparency exceptions, including salaries and M&A
“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 inc…”
Sid Sijbrandij: Leaders should separate feedback reception from feedback evaluation
“Feedback doesn't have to be correct in order for you to welcome it. Like it, there's two phases. There's just being thankful that someone's giving feedback and then you decide what to what to accept.”
Sid Sijbrandij: Laziness is often a symptom of perfectionism, not underperformance
“I think laziness is almost a shortcut. That's too easy. Like what's going on in their life. And 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 two of a high bar for the output and the end result, and I p…”
Sid Sijbrandij: GitLab maintains a public employee handbook of over 2,000 pages
“We have a strong written culture and it shows in our handbook of over 2000 pages where we detail how we work.”
Sid Sijbrandij: Synchronous communication is best for urgent, broad group projects
“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.”
Sid Sijbrandij: Pitch a specific 10-minute problem instead of generic mentorship
“I think what's really, what I see sometimes is that people reach out and ask whether you want to be their mentor. And I think that's Unlikely to be a yes for me, but I think also from other people. I think you want to kind of, you want to start small, iterate …”
Sid Sijbrandij: Board members are a founder's boss, not their mentors
“Board members are not mentors per se. They're your boss, which is very different, but still there's an enormous amount of things you can learn.”
Sid Sijbrandij: Boards expect CEOs to present diagnostic solutions when missing targets
“They know a startup is up and down, but they want you to completely understand the problem and have a plan on how to deal with it.”
Sid Sijbrandij: GitLab limits live board meeting presentations to two minutes
“Now at GitLab, we've taken that to a bit of an extreme where we send video clips of us presenting the slide deck up front, and we do, if we do presentations, it's like two minutes.”
Sid Sijbrandij: Founders must specify three help requests before board meetings
“Now, what's super important is that before the board meeting, you say, these are the three things I would really love feedback on. I could use help on. Make, tell them what to help you with.”
Sid Sijbrandij: Board members should only ask questions, not direct operations
“As a board member, you should really only be asking questions and getting informed and”
Sid Sijbrandij: GitLab board meetings include a 45-minute closed session
“Those of us are one and a half hours open session, and then about 45 minutes closed session. So 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 CEO and then 15 without the CEO to e…”
Sid Sijbrandij tested Series B investors with mock board strategy discussions
“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 waited for them to kind of wait it. We discussed and asked them to add value and then what you get back, how that…”
Sid Sijbrandij: Matrix organizational structures make executive life difficult
“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…”
Sid Sijbrandij: DIY DevOps with custom tool integrations is dead
“That DIY DevOps is dead. Like the area of selecting 10 best in 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.”