This page details processes specific to Sid, CEO of GitLab. The page is intended to be helpful, feel free to deviate from it and update this page if you think it makes sense. If there are things that might seem pretentious or overbearing please raise them so we can remove or adapt them. Many items on this page are a guidelines for our Executive Business Administrators (EBAs).
Sid Sijbrandij is the Co-founder, Chief Executive Officer and Board Chair of GitLab Inc., the DevSecOps platform. GitLab’s single application helps organizations deliver software faster and more efficiently while strengthening their security and compliance.
Sid’s career path has been anything but traditional. He spent four years building recreational submarines for U-Boat Worx and while at Ministerie van Justitie en Veiligheid he worked on the Legis project, which developed several innovative web applications to aid lawmaking. He first saw Ruby code in 2007 and loved it so much that he taught himself how to program. In 2012, as a Ruby programmer, he encountered GitLab and discovered his passion for open source. Soon after, Sid commercialized GitLab, and by 2015 he led the company through Y Combinator’s Winter 2015 batch. Under his leadership, the company has grown with an estimated 30 million+ registered users from startups to global enterprises.
Sid studied at the University of Twente in the Netherlands where he received an M.S. in Management Science. Sid was named one of the greatest minds of the pandemic by Forbes for spreading the gospel of remote work.
A pronunciation hint for Sijbrandij: It’s like when you have seen some distilled wine, and want to point it out: Sid, see brandy
Moved to a google document internal to GitLab team only. Please search in Google Drive file name: CEO's Favorite Restaurants. If you have questions please message the Staff EBA to the CEO in #eba-team or DM.
Transparency and directness are part of our values and I want to live them by sharing the flaws I know I have. I'm fully responsible for improving the things below, listing them is no excuse. They are listed here for two reasons. The first one is so that people know it is not them but my fault. The second one is so I can improve, I hope that listing them lets people know I appreciate when people speak up about them.
If you speak up about them I should thank you for it, it is OK to say 'this was on your list of flaws so I kinda expected a thank you'. I'm sure I have more flaws that affect my professional life. Feel free to send a merge request to add them or communicate them anonymously to one of our people operations team members so that they can send a merge request.
Not a flaw but something to know about me, I have strong opinions weakly held. Or as someone said, I come in hot but am open to new evidence.
Sid is easy to talk to on any subject. He is good at drawing people out and challenging them to grow, in a supportive way. He can meet anyone on their level and have a productive conversation. Watch a quick video from a CEO Shadow recounting her observations.
It’s not a “best practice”, it’s a “boring solution”. The product categories page is a good example. Sid advocates for using MECEFU terms to keep communication efficient.This section was started by GitLab's Head of Remote Darren M. to coach and provide context to others who meet with and interview Sid. The below are suggestions based on a history of personal interviews, extracted lessons from GitLab Unfiltered interviews, and observations during a CEO Shadow rotation. Others are welcome to create a merge request and add more.
Thanks to Mårten Mickos for the inspiration for this section. All good ideas are his, all bad ones are mine.
I am a visual person much more than auditory, and I am a top-down person much more than bottom-up. This means that I love written communication: issues, email, Google Docs, and chat. Feel free to send me as many emails and chat messages as you like, and about whatever topics you like. I prefer chat over email.
If you have a great new idea or suggestion for me, I appreciate if you can convey it in a picture or in written words, because I learn by seeing more than I learn by hearing. I don't mind if you send me or point me to plans that are in draft mode or not ready. I am happy if I can give useful feedback early. It doesn’t have to be perfect and polished when presented to me.
In written communication, I appreciate the top-down approach. Set the subject header to something descriptive. Start the email by telling me what the email is about. Only then go into details. Don't mix separate topics in the same email, it is perfectly fine to send two emails at almost the same time. Try to have a concrete proposal so I can just reply with OK if that is possible.
I get many email on which I am only cc'd on, I would very much appreciate if you started emails intended specifically for me with "Sid," or some other salutation that makes it clear that the message is for me.
Share slide decks in advance of meeting with me per no presenting in meetings communication guideline. I can be tagged in a relevant Slack channel.
When sharing slides with me, limit the content on each slide to one concept. Avoid condensing multiple concepts into one slide. Additionally, the slide title should be specific to the content on that slide. For example, instead of condensing two lists onto one slide, separate the lists onto two separate slides with slide titles specific to each list.
This also applies if you are providing slides for me to present.
I have accounts on LinkedIn and Facebook. I will not send invites to team members on those networks since as the CEO I don't want to impose myself on anyone. But I would love to connect and I will happily accept your LinkedIn and Facebook friend request. Please ping the Staff EBA to the CEO in #eba-team on slack and they will accept your connection request. You can also find me on Twitter as @sytses, I won't request to follow private twitter accounts, I assume I'm welcome to follow public twitter accounts, if not please let me know.
Sometimes I will ask to be kept apprised of an action item or follow up. One common way for me to express this desire is by applying the CEO Interest label on a GitLab issue. When keeping me apprised please tend toward over-communication. The primary method to communicate your follow up to me should be via MR or issue updates posted in the #ceo slack channel including specific notification when an issue is completed or closed. It might feel like you are being bothersome or distracting, but it is not. If I ever feel like you are truly over-communicating, I will let you know.
I get a lot of @ mentions in Slack, often when I'm being discussed. Please only @ mention me when you need me to see something or approve something, when you just want to refer to me you can just say Sid. This saves time and enables increased efficiency.
I’ve been thinking about the notion of Sacred Cows since I heard that people use “Sid said” as an argument in conversations.
The phrase comes from the belief of devout Hindus that cows are sacred animals and should never be harmed. In the US, we use this term to mean “one that is often unreasonably immune from criticism or opposition.” If we’re truly practicing continuous learning, we have to question the Sacred Cows that can subtly and profoundly influence how we make decisions and conduct business. We need to examine Sacred Cows with ruthless compassion. By that I mean that we should be ruthless about examining and questioning their validity while being compassionate with the person citing the Sacred Cow.
Just because I said something doesn’t make it inviolable law like a law of physics. My utterances are usually merely an opinion based on the context of the discussion and the moment. As new context is revealed, we need to be willing to reexamine what we say and iterate.
What I propose is that next time ‘Sid said’ is mentioned you check in with me, I might say:
But it is also possible that:
Please follow these steps if you'd like me to review a Merge Request (MR) for approval:
@sytses as a Reviewer to the MR. You can use this quick action: /assign_reviewer @sytses.@ mentioning me asking for my review. Please provide a brief description sharing the context.#3 above)I prefer other forms of communication (e.g. slack) over email. I get a lot of email and I'm frequently not on top of it. I appreciate it if you send my EBA a slack message if I need to respond to an email. Please quote the subject line of the email in your chat message.
If someone else in the company wants to have me send an email they should email me and cc my EBA with:
When receiving such an email my EBA should stage a draft email to the recipient and a draft answer 'done'.
The email should only be the body. Greetings and niceties are handled by the EBA.
For scheduling a video call or meeting with me or other execs, please see the EBA handbook page. Please do not use Zoom waiting rooms for meetings scheduled with me or on my behalf. If attendees are joining separate sections of a meeting, you can break the session into multiple Zoom calls or have a Slack channel to manage attendee entrances and exits.
As part of my role, I participate in a variety of meetings both internal and external. Please see below for a general overview of these.
I try to plan my vacations around times when many team members in the United States are on vacation. A rough overview of these times is captured on GitLab's cadence page. Other team members may also preference taking off work during these windows as there tends to be less demand for synchronous collaboration during these times.
To schedule a Pick Your Brain interview with me, please see the EBA handbook page. To watch and read prior Pick Your Brain interviews about all-remote, please see the Interviews page.
For scheduling a video call or meeting with me or other execs, please see the EBA handbook page.
To schedule Sid to speak at an external engagement please contact the EBA to the CEO with the details outlined in the Executive External Event Brief. The EBA to the CEO will gain approval from the function head of the requestor on whether the CEO will attend or not. Sid's preference is to participate in 1:1 fireside chats or conduct a stand alone presentation (audience Q&A is fine). He does not participate in panels with multiple speakers.
If the organizer of an event requests a prep meeting with Sid to check audio and visual before a remote presentation, we can schedule for 5 minutes before the event for Sid to login and confirm that audio and visual are working as expected. A longer prep meeting is not required as Sid has a robust remote work setup.
Some general guidelines of what travel is appropriate, these guidelines are not fixed, feel free to ask for exceptions:
Consider the following to increase efficiency:
When at conferences I want to achieve results for the company and be efficient with my time. Please ask sales and/or marketing to set up meetings for me in advance. I don't mind doing booth duty, presenting, or any other way I can contribute. I do mind unscheduled time randomly wandering the hallways, I've found this to be ineffective.
Each year I want to attend the Linux Foundation Member Summit (formerly the Open Source Leadership Summit). Please ensure:
If I am asked to keynote a conference, it is up to the executive of the function asking me to attend to decide. For example, if the request is coming from marketing, the CMO decides; if the request is coming from Finance, the CFO decides. Please follow the process outlined under meeting request requirements and work with my EBA who will shepherd the decision about whether or not I will attend.
If possible, I use a teleprompter when giving keynotes. I prefer to use the teleprompter app "PromptSmart" along with the "PromptSmart Remote Control." Ideally, someone will scroll through the script on my behalf, at my pace.
I'm always willing to record video content for conferences I'm unable to attend. Email my EBA to coordinate the recording.
Often when attending an event, the organizers will reach out to see if I want a certain snack or drink. If possible, I would prefer:
People regularly ask what I use for my home office setup. Below is a list of the items I use:
Note: I have paid for all of these items myself. Please refer to GitLab's expense policy for office equipment and supplies when purchasing and expensing home office items.
When preparing scripts or documents in my voice, please follow these guidelines. This list can help you prepare a draft that is as close as possible to my natural way of communicating. For additional information or questions, please contact the #external-comms Slack channel or the Chief of Staff to the CEO.
The CEO will pay for all transport expenses (flight, Uber, etc.) personally. By default flying business class. On short flight with other team members fly economy if we can sit together, in this case still pay personally.
There are three levels of performance:
I'm driven by what is possible, the aspiration, what can be. Others' expectations of a person affect the person's performance with high expectations leading to better performance, this is called the Pygmalion effect. What is possible is more than what we are satisfied with or what we promised to our stakeholders. We can be above what we promised and below what is possible and still have done a good job, we can win without doing everything we aspired to do, or everything that is possible. It is unlikely that we win without doing what we promised. I have to be clear in distinguishing these level when I discuss a goal with my reports.
One of the hardest things in business is not to slow down as the organization grows. An applicant asked how we manage to do this and these are the factors that come to mind:
As the company keeps growing my use of the handbook is also changing.
These monthly office hours are an opportunity for GitLab team members to discuss how to take a more iterative approach to a specific activity or to highlight how a more iterative approach helped drive results. Iteration is one of the hardest things to learn about working at GitLab and these office hours are a great opportunity for me to help coach folks who are interested in better understanding it. We learned iteration at YC, where we took our plan for the next 3 months and compressed it into 2 weeks. Give yourself a really tight deadline and see what you can do. The smaller we split things up, the smaller steps we take and the faster we can go.
I keep in touch with various industry leaders on a regular basis (monthly, quarterly or annually). They are people who have accomplished extraordinary things at prominent companies such as hypergrowth hiring, ambitious revenue growth, or created transformative technologies. In these meetings, I get to learn from and know senior leaders within the industry. This helps me to understand what great looks like as it offers me a lens into other companies and what has made them successful or held them back. I ask questions about how they would approach GitLab's current challenges or opportunities. I often share insights from my conversations with functional leaders and other team members.
I have these conversations across all functions because it is important for me to have external, subject-specific mentors. Better understanding individual functions helps me set better targets, ask better questions, and be a better partner to functional leaders. This allows me to be a better manager and CEO.
I try to prioritize people from underrepresented groups, because I see value in learning from folks with different backgrounds. These same folks may eventually become GitLab team members who would add diversity to GitLab.
See CEO and executive fraud in the security practices section of the handbook.