20VC Gitlab CEO Sid Sijbrandij on Why You Are Not Allowed to Present in Meetings at Gitlab, Why it is a Pipedream We Will Go Back to Offices and What is the Future of Work & CEO Coaches; What Makes The Best, When To Have Them and When To Change Them

In a dynamic discussion on 20 VC, host Harry Stebbings welcomes Sid Sijbrandij, the founder and CEO of GitLab, to delve into the company's journey from its open-source origins to a public entity, with over 1500 employees and 30 million users. Sid highlights GitLab's integrated DevOps platform's role in streamlining software delivery and enhancing security. He also discusses the benefits and challenges of GitLab's all-remote work model, including fostering informal communication and the necessity of asynchronous collaboration across time zones. Sid shares insights on leadership, emphasizing transparency, iteration, and results, and the evolution of his management style. The conversation touches on mentorship, the significance of a written company culture, and the future of work, underscoring the shift towards remote and hybrid models. Sid reflects on board management, investor selection, and his personal venture, Open Core Ventures, which fosters companies around open-source projects.

• Sid is the founder and CEO of GitLab, a company that provides a single application for the entire software development lifecycle.
• GitLab went public late last year, growing to over 1500 employees and over 30 million registered users.
• Sid has raised funding from iconic investors such as GV, Tiger CO2, and D1.
• He is an active angel investor and sits on the board of Meltano, a data management tool spinout from GitLab.

"GitLab's single application helps organizations deliver software faster and more efficiently, while also strengthening their security and compliance prior to their IPO late last year, Sid raised something from some of the best in the business, including iconic, GV, Tiger CO2 and D one, to name a few."

This quote explains GitLab's core product offering and highlights the successful fundraising efforts led by Sid, which involved securing investments from prominent venture capital firms.

• GitLab was started by Sid's co-founder, Dimitri, who wanted a better way to collaborate on software development at work.
• The platform covers all stages of software development, including planning, building, testing, security, deployment, monitoring, and improvement.
• GitLab became popular because it offered a unified experience for the entire development cycle, leading to efficiency gains for users like Goldman Sachs.
• Sid saw the potential in Dimitri's open-source project and decided to turn it into a full-fledged company.

"It started when I saw GitLab, which was created by my co-founder Dimitri... Today GitLab is over 1500 people."

The quote provides a brief history of GitLab's inception, emphasizing the transition from an open-source project to a company with a significant number of employees.

• GitLab has always been a remote-first company, even before it became a common practice.
• The company evolved organically into a remote work culture, starting with international hires and continuing even when hiring locally.
• The remote work model scales well with company growth and GitLab has developed practices to ensure effective remote collaboration.

"We started off as a remote company... It organically evolved like that."

This quote highlights the natural evolution of GitLab's remote work culture, which began from the company's inception and continued as it grew.

• GitLab uses "coffee chats" as a way to replicate water cooler conversations in a remote work environment.
• New employees are encouraged to have at least five coffee chats to integrate this practice into the company culture.
• The company also supports in-person gatherings and makes participation in such events optional.

"We do a ton and we give a ton of examples, but one of the things we do is coffee chats... You don't necessarily need to talk about work."

This quote explains one of the key strategies GitLab employs to maintain informal communication among remote employees, which is critical for building trust and company culture.

• The most challenging aspect of transitioning to remote work is facilitating informal communication.
• Companies often focus more on the logistics of returning to the office rather than improving remote work practices.
• Sid advises companies to be intentional about creating opportunities for team members to connect on a personal level.

"I think this informal communication is the most important thing... You need to be intentional about creating time and space, to learn more about each other, to build trust."

The quote emphasizes the importance of intentional efforts to foster informal communication in a remote work setting, as this is often what employees miss the most when not in a physical office.

• The future of work is trending towards all-remote startups, which don't have physical offices.
• Legacy companies may continue with full co-location, which has been proven effective pre-pandemic.
• Hybrid models can be effective if structured properly; all employees should be in the office on the same days.
• Ineffective hybrid models have some employees always remote and others always in-office, leading to talent loss.

"I think the future of work I see a lot of startups are being all remote. They don't even have an office. So that's going to happen and that's going to happen more and more often."

This quote emphasizes the growing trend of startups adopting an all-remote work model without the need for a physical office space.

"The type of hybrid that works is you come into the office some days and I think companies are going to find out that it should be the same day. So everyone's at the office at the same time."

Here, the speaker suggests that an effective hybrid model involves having all employees work in-office on designated days to ensure team cohesion.

• Overcoming time zones is challenging; work should be done asynchronously.
• GitLab aims to work more asynchronously and have a broader geographic distribution in its executive group and board.
• GitLab currently has employees in over 60 countries, reflecting a diverse and distributed workforce.

"The hardest thing about remote time zones, to overcome time zones, you need to work asynchronously. Very, very hard."

This quote highlights the difficulty of navigating time zones in remote work and the need for asynchronous communication to address this challenge.

• Not all meetings are necessary; many could be replaced by asynchronous communication.
• GitLab discourages presenting in meetings; Q&A sessions are more valuable for synchronous meetings.
• The speaker integrates family calls into their schedule to prevent work overlap and advocates for asynchronous preparation for meetings.

"The other thing was a prep for this call. It was a ten minute prep, and there's a really good document about how I should prepare and all the questions you might ask and everything else."

This quote suggests that meeting preparation can often be done asynchronously, using shared documents instead of live calls.

• GitLab's top values are results, iteration, and transparency.
• The speaker strives to be a transparent leader, seeks to iterate quickly, and bases decisions on results.
• Over time, the speaker has learned to delegate more, be patient, and provide context for better decision-making.

"So I hope I strive to be a leader who's transparent, who iterates are always looking for the smaller thing that could be done faster."

The speaker describes their leadership style as transparent and focused on continuous improvement through iteration.

• GitLab is transparent by default but has a list of items that remain confidential, like salaries and M&A.
• Transparency regarding fundraising depends on market conditions and company attractiveness.

"Because we're transparent by default. We have the longest list of things that aren't transparent."

The quote confirms GitLab's default stance on transparency while acknowledging that certain topics are kept confidential.

• People are naturally inclined to give feedback; the challenge is ensuring they feel rewarded and not penalized for it.
• Feedback is welcome regardless of its correctness, and acceptance depends on frequency, source credibility, and the source's expertise.
• Creating a safe environment for feedback, especially in group settings, is crucial for a healthy company culture.

"You got to be very cautious of making sure you're open to feedback, thanking people for it, and making that a very normal thing."

This quote emphasizes the importance of fostering an environment where feedback is not only welcomed but also appreciated.

• Leaders must temper their emotions, especially when caring deeply about their work.
• At GitLab, questioning people's intentions is discouraged; understanding their circumstances is encouraged.
• Situational leadership theory is favored, varying leadership style based on the situation and human element.

"It's hard what we try to do at GitLab, which is super hard. Don't question people's intentions."

The speaker advises against assuming negative intentions behind people's actions, advocating for understanding and empathy.

• A written culture involves documenting processes and decisions.
• It's important for leaders to manage their emotions and not react out of frustration or anger.
• The speaker acknowledges the challenges of being level-headed and the benefits of working with humans over robots.

"Then a written culture means you write things down."

This simple statement encapsulates the essence of a written culture, where documentation is a central practice.

• Harry Stebbings discusses the factors that influence his decision to delegate tasks.
• The process of delegation varies depending on who is on the receiving end.
• Effective leadership involves adapting one's style to different situations, making leadership a continuously evolving skill.

"I've made a blog post in November with 19 factors I can consider, and I sometimes do consider, when to delegate something."

This quote outlines that Harry Stebbings has a thoughtful approach to delegation, considering multiple factors before deciding to delegate, as detailed in his blog post.

• Sid describes the benefits and drawbacks of a strong written culture.
• A comprehensive handbook can reduce the need for synchronous communication and improve efficiency.
• The challenge with written communication is the time required to provide sufficient context for those lacking it.
• Synchronous communication may be preferable for urgent issues involving a wide group without shared context.

"In our handbook of over 2000 pages, we detail how we work."

Sid emphasizes the extent of their written culture by referencing the length of their handbook, which serves as a detailed guide on company operations.

• Sid finds mentorship extremely valuable and enjoys mentoring startups and individuals at GitLab.
• He suggests that a direct request to become someone's mentor is less effective than asking for advice on a specific problem.
• Building a mentor relationship should start with a small, focused interaction rather than a broad request.

"Mentorship is super important. I've been helped by a ton of people in my career."

Sid acknowledges the significant impact mentorship has had on his career and its importance in professional development.

• Sid credits CEO coaches and board members as key sources of learning and mentorship.
• He recounts a pivotal moment where a CEO coach helped him prepare for a challenging board meeting.
• The advice from a mentor or coach can be simple yet profoundly impactful in critical situations.

"Godfrey Sullivan, our lead independent, he helps me, the situational leadership, like varying my staff."

Sid highlights the specific guidance he received from Godfrey Sullivan on situational leadership and adapting his management style.

• Sid advocates for CEO coaching, especially for leaders of fast-growing companies.
• Finding a CEO coach is a two-way process where both parties must find the relationship compelling.
• The typical duration with a coach is a few years, depending on the company's stage and the CEO's growth.

"If you're the CEO of a fast growing company, I totally recommend it."

Sid recommends CEO coaching for leaders in rapidly expanding businesses, emphasizing its benefits for personal and professional growth.

• There is no exact science to knowing when you've learned all you can from a coach.
• The indication of a plateau in learning is when the same advice is repeatedly given.
• CEO coaching can sometimes overlap with therapy, but it is generally preferred to keep them separate.

"It's leveling off and you start hearing the same things more and more."

Sid describes the signal that indicates it might be time to seek a new coach when the learning from the current one begins to plateau.

• Sid shares insights from managing GitLab's board and being a board member for Meltano.
• Board members dislike long presentations; it's better to focus on discussion and areas where the board can provide help.
• Clearly communicating the specific areas where help is needed can lead to more productive board meetings.

"What's super important is that before the board meeting, these are the three things I would really love feedback on."

Sid stresses the importance of guiding board members on where their input is most valuable to avoid wasting time and effort on irrelevant issues.

• As a board member, it's essential to ask questions rather than operate as an executive.
• The best board members provide high-value input without feeling the need to prove themselves.
• Board members should complement each other's expertise and be confident in their contributions.

"Great board members, in my view, very knowledgeable, very high signal to noise."

Sid outlines the qualities of great board members, highlighting the importance of expertise and the ability to contribute meaningfully without dominating the conversation.

• When faced with tough feedback from a board member, it's challenging to decide whether to discuss it privately or in the full board meeting.
• Public discussion can benefit from collective insights, but it risks creating a confrontational atmosphere.

"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?"

Harry Stebbings expresses the dilemma of how to approach sensitive topics during board meetings, weighing the pros and cons of private versus public discussion.

• Distinction between issues originating from the company's strategy versus CEO's decisions.
• Importance of addressing company problems, like incorrect market strategy, in board meetings.
• The CEO should own the decisions and not attribute them to the board.
• GitLab's practice of allowing many participants in board meetings and managing the associated risks.
• Emphasis on asking challenging questions without dictating specific strategic changes.

Is it a company problem or is it a CEO problem? So if it's, it's a company problem, dramatically around photo market strategy is wrong. That's exactly what a board meeting should be about.

This quote highlights the importance of identifying the nature of a problem—whether it belongs to the company's overall strategy or the CEO's actions—and addressing it appropriately during board meetings.

• GitLab's open and transparent approach to board meetings.
• Duration and structure of board meetings: 1.5 hours open session, 45 minutes closed session.
• Closed session divided into parts with and without the CEO to discuss performance and set context.
• Importance of pre-meeting closed sessions for setting expectations and acknowledging team members' contributions.

We have a great page on board meetings, so if you Google GitLab board meetings, you'll find more information.

This quote suggests that GitLab has a resource available online that provides detailed information about their board meeting practices, indicating a commitment to transparency and openness.

• Importance of selecting investors with a good reputation and constructive attitude.
• Preference for investors who can contribute significantly to board meetings.
• The practice of conducting a strategy discussion with potential investors to gauge their value-add.

So you select firms with a good reputation, that they're constructive, and then you select people frequently.

This quote reflects the criteria used by GitLab for choosing investors, emphasizing the importance of reputation and the ability to contribute constructively to the company's governance.

• Sid's favorite book is "High Output Management."
• The book's integration of situational leadership principles.

High output management? And I love how kind of situational leadership is kind of woven into that.

This quote reveals Sid's appreciation for a management book that incorporates situational leadership, suggesting its influence on his leadership style.

• Difficulty in implementing cross-functional initiatives due to organizational boundaries.
• Trade-offs in company structure: functional, project-based, or matrix organization.
• Each structure presents unique challenges, with matrix organizations being the most complex.

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

This quote explains why cross-functional initiatives are particularly challenging at GitLab due to its functional organizational structure.

• The shift away from DIY (Do It Yourself) DevOps practices.
• The inefficiency and ineffectiveness of maintaining custom integrations between multiple DevOps solutions.

DIY DevOps is dead. The area of selecting ten best in class solutions for DevOps and then having custom integrations between them that you maintain that is no longer working.

This quote signifies a change in the DevOps landscape, with Sid declaring the end of DIY DevOps due to its unsustainable nature.

• Prediction of more, differentiated, and opinionated cities in the future.
• Cities becoming more proactive in attracting residents, potentially through recruitment efforts.

I think there will be more cities, more differentiated and opinionated, and they will be more welcoming.

This quote reflects Sid's vision for the evolution of cities, suggesting increased diversity and a more active approach to population growth.

• Sid's involvement in creating companies around open source projects through Open Core Ventures.
• The venture's methodology: investing early, co-creating companies, and building proprietary offerings on top of open source projects.

I started open core ventures together with Betty as coo, and we create companies around open source projects.

This quote explains Sid's strategy for personal investments, focusing on leveraging open source projects to create new companies.

• GitLab's marketing strategy included a billboard showcasing their DevOps platform's impact on T-Mobile.
• The billboard highlighted a tenfold increase in deployment frequency for T-Mobile using GitLab.

The billboard was on the 101, and it said GitLab, the one DevOps platform.

This quote describes a specific marketing initiative by GitLab, illustrating the effectiveness of their platform through a customer success story.

• Acknowledgment of the need to be more positive in meetings.
• Implementation of a feedback system with CEO shadows rating Sid's performance in meetings.

Sid, I could be more positive in meetings. And what I do is I have CEO shadows who attend like 80% of my meetings, and they rate me for every single meeting.

This quote reveals Sid's self-identified area for personal development and the unique feedback mechanism he has put in place to address it.

• Anticipation of rapid adoption of platforms in the tech industry.
• GitLab's goal to integrate more of the toolchain into its leading platform.

So we have this amazingly rapid adoption of platforms. And then those platforms with GitLab as the leading one, will consume more and more of the tool chain.

This quote outlines Sid's long-term vision for GitLab's growth and dominance in the DevOps toolchain market.

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This quote is part of an advertisement for Squarespace, emphasizing the integrated services it offers for building and managing an online business presence.