Sid Sijbrandij: "What has served me well in life is to follow my own curiosity."

Spring! It’s May, and Mother’s Day weekend has just passed. I hope you had an opportunity to celebrate the mothers in your life this weekend and/or exercised self-kindness if that is a role you have filled.

Springtime has always felt like a time of strength and renewal, inspiring visions of growth. The month of May is when this growth takes root and blossoms.

Fittingly with the theme of May and its spirit of renewal and growth, I connected with Sid Sijbrandij, Co-founder, CEO, and Board Chair of Gitlab Inc., The One DevOps Platform. GitLab has pioneered innovative internal programs and processes, and is believed to be the largest all-remote company from day one. Sid views remote work as the springboard for the company’s core values of collaboration, results, efficiency, diversity, inclusion & belonging, iteration, and transparency.?

Sid’s career path has been anything but traditional. He has spent time building recreational submarines and worked on the Legis project, which developed several innovative web applications to aid lawmaking. He taught himself how to program after falling in love with Ruby code in 2007, and in 2012 he encountered GitLab and discovered his passion for open source. Not long 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. It was a pleasure to cheer on the GitLab leadership team as they rang the opening bell when they went public in 2021. It is an honor to serve as a board member of this forward-thinking organization.

I admire Sid’s vision of transparency - one that firmly believes that everyone should have full context and information required to excel.? At GitLab, Sid implements this vision via several different avenues, including the CEO Shadow Program. The program allows GitLab team members to gain a broad perspective of how decisions are made by following Sid’s conversations at the company for two weeks. It is not a performance evaluation and in fact, the feedback goes both ways - participants are encouraged to deliver candid feedback to Sid directly throughout the two-week program. GitLab also publicly makes their company handbook, available in a compliant manner, taking “sharing is caring” to a new level.

To stay engaged with these conversations, be sure to subscribe here for all Lift As We Climb interviews. Today, let’s hear from Sid.

Saintil: What are some habits or routines in your day-to-day life that keep you focused and goal-oriented?

Sijbrandij: I like to have the same schedule every work day. I tend to get up at 5:30am PT, start my workout by 5:45am PT for about an hour, and do my first call at 7:30am PT. My meetings have 5 minute breaks in between, so I have time to grab a snack, or to respond to messages, or things like that. I like to take weekends off to relax, spend time with my family and friends, recharge, and gain new perspectives. Prioritizing things outside of working hours, such as calls with family and dinner with friends, also helps me gain new perspectives and achieve work life integration.?

What has served me well in life is to follow my own curiosity.?

Saintil: Pretend you get a visit from your future self; what would your future self tell you to focus on?

Sijbrandij: What has served me well in life is to follow my own curiosity. I think Chris Dixon put it well when he said, “What the smartest people do on the weekend is what everyone else will do during the week in ten years.”

?…you need to take a step back, remove emotion from the discussion, and try to devise a way for everyone to acknowledge the problem.?

Saintil: How do you navigate challenging times while encouraging positivity without pushing past the issue?

Sijbrandij: For me, the hardest thing is friction between people. Conflict is common in many high performing, rapid growth organizations and something that all leaders in these environments must manage. To do so, you need to take a step back, remove emotion from the discussion, and try to devise a way for everyone to acknowledge the problem. It’s critical to allocate time to focus on the conflict so that the individuals can build trust and move forward collaboratively.? Sometimes the most effective way to ensure everyone acknowledges the issue is by involving an external party such as a professional coach or mentor. Crucial conversations are a skill many managers and individual contributors need to learn, so GitLab has a handbook page and offers training to empower our team members.

Saintil: What are some of the qualities of leadership you admire?

Sijbrandij: Admirable leadership qualities include clarity in the goals that should be reached and clarity in why the goals are important. Accurate assessment of people's performance in the role is also an important leadership skill. Successful leaders are able to iterate by reducing scope to get something done quicker.?

I am intentional about being a good manager which includes being open to feedback and being vulnerable.

Saintil: How are you lifting others up in your personal or professional life?

Sijbrandij: In my work for GitLab, I am intentional about being a good manager which includes being open to feedback and being vulnerable. In practice, this looks like sharing my performance review with all of my reports and Directs-Group (https://about.gitlab.com/company/team/structure/#directs-group). I also encourage talking about mental health and using GitLab’s mental health benefits, when needed.?

Another way to pass on knowledge and support people is through coaching. I encourage coaching for all team members, and have connected some of my direct reports to the coaches that can help them thrive in their roles. I have benefited from coaching throughout my career and continue to meet regularly with a coach to help me continue to grow and be impactful in my role.?

I also coach both current and former team members. I meet with them on a regular basis and document our meetings with a 1:1 agenda. This gives us a reference to the things we work on and the discussions we have.?

I donate to multiple charities. GiveDirectly and The Last Mile are two of my favorites. GiveDirectly allows for direct cash transfers which I think is a great way to help people so they can address their most urgent needs. https://www.givedirectly.org/ The Last Mile is helping people who are currently or formerly incarcerated individuals for successful reentry through business and technology training. https://thelastmile.org/

My personal foundation also matched GitLab Team Member donations to multiple charities to help people affected by the military invasion of Ukraine. https://about.gitlab.com/blog/2022/03/11/gitlab-actions-to-date-regarding-russian-invasion-of-ukraine/#supporting-ukrainians

Be sure to subscribe here if you want to receive all our future Lift As We Climb interviews. Check out our previous interviews with:

• David Hornik, Founding Partner at Lobby Capital
• Erica Schultz, President of Field Operations at Confluent