I spent two weeks in GitLab’s CEO Shadow program — ten-plus meetings a day alongside the CEO and his direct reports, covering everything from investor calls to media interviews to one-on-ones.
I came out with 16 merged company handbook contributions, a few surprises (an investor asked a security question mid-meeting and Sid handed it to me on the spot), and a much clearer picture of how a fully remote company actually operates.
A few things stuck with me. GitLab’s handbook is a guidebook, not a rulebook — something I didn’t fully appreciate until I saw how people referenced it in real decisions. Meetings were prepared in advance, structured around the most contested topics first, and cut short when necessary. When an interview candidate mentioned kids at home near the end of their session, Sid scheduled a follow-up rather than push through. Small thing. Said a lot.
The quote that’s stayed with me: “You can’t train people on a culture. You have to live it to learn it.” Two weeks of watching GitLab’s values play out in actual decisions made that are real in a way no handbook ever could.
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