Reflection on my CEO shadow rotation at GitLab

I spent 2 weeks being a CEO shadow at GitLab, and thought I’d reflect a bit on my experience. If you’d like a more thorough write up, check out Darren Murph’s takeaways and lessons learned blog post, or check out the CEO Shadow YouTube playlist.

The basics

Everyone at GitLab has the opportunity to do a rotation in the CEO shadow program (provided they meet the criteria, but “last minute” open rotations anyone can take). It’s 2 weeks where you learn the first week and teach the second week, overlapping with two other CEO shadows.

The daily routine is what you’d expect. We join most of the meetings that our CEO, Sid Sijbrandij, has; taking notes, and timekeeping.

The meetings are a mix of internal and external including board, executive group, 1:1 (one-on-one), investors, customers, and startups that he’s funded.

When not part of a meeting, we work on short term tasks that come up, (when remote) mostly changes to the website or handbook. Just one example is readding support as a paid feature on our pricing page. You can see all the merge requests that CEO shadows have done, and the list of typical tasks.


I will note that I’m really glad they formalized the 2 week rotation with overlaps with another CEO shadow. It’s not always easy to keep up with the conversations when notetaking, and it’s great to have someone to ask questions of. Being a shadow can be tiring, many having counted over 100 meetings attended in 2 weeks (though I got off lightly with 72). Especially in the first week, it’s comforting to know you have someone to lean on if you need it.

If there are a bunch of tasks, you can also split the work to get things done faster. Sometimes, things aren’t as easy as they may seem, and collaborating on them means making it easier and getting it done faster.

Company insights

Aside from getting insight into how our CEO works, the biggest thing and really the goal of the program is getting a view into how the company functions at the highest strategic level. As companies grow bigger, velocity is often a concern. Generally though, meetings are run and decisions are made efficiently, with no “presenting” (though often brief summaries or updates are provided).

Close to year end is a particularly interesting time to join meetings because there are a number of discussions around finalizing the list of initiatives and projects to focus on for the next fiscal year along with how to resource them. I’ll be keeping in mind some of what’s on the list and seeing a bit of how that ends up trickling down to the individual contributor level.

Next quarter’s OKRs (objective and key results) are also being drafted around this time. While those OKRs will likely not directly impact my everyday work, they obviously affect the company on a higher and usually more long term basis. You can see GitLab’s OKRs if you’re interested.

Some of the most interesting conversations are of course around things that aren’t super smooth: is loss accepted? or are things course corrected? How is course correction decided on? What kind of course correction happens? I’ve seen some of this at the management level for our team, and it was intriguing to see many similarities in how these situations were handled at the top level (though unsurprisingly I suppose).

Living the values

GitLab is well known for its values.

There have been a few people during my time at GitLab that I believe embody the values and lead by example in demonstrating the values, and at the top of that list has always been Sid.

Too many companies write values because it’s good for the business, but don’t make them actionable. I think it says a lot about the company that our CEO is intimately familiar with what’s on the page, and is often the one pushing us to live up to them.

Probably one of the things most interesting for those outside of GitLab is that Sid will often publicly livestream discussions he has with people from other organizations. For example, he livestreamed the discussion with Sourcegraph’s CEO on a CEO’s partnership with the Chief of Staff:

There are too many subvalues that I saw “in action” to list, but the ones that stood out to me are the ones that are often difficult to do, or to do consistently:

Giving and receiving feedback

As the section on giving feedback says:

Giving feedback is challenging, but it’s important to deliver it effectively.

Sid regularly says thanks, and gives great positive feedback to others. He’s also generally good at giving critical feedback, focusing on the work and results.

While I didn’t see any significant instances, he’s also known to be very receptive to feedback, outlining flaws on the CEO page, specifically mentioning that you can speak up about them.

I don’t know that he’s the best feedback giver, but I definitely appreciate how often he provides both specific and general positive feedback. It really stood out to me.

The fun

It’s not all “serious”. There are minutes here and there where we get to chat with people before meetings start, and depending on the people in the room, banter occasionally happens.

Just for the fun of it, following another recent shadow’s example, I included “quote(s) of the day” in my daily reports. The best lines typically came from external meetings, such as:

  • “The Chief of Staff makes me look like a much better CEO than I really am.”
  • “You don’t have to smell the other person.”

The funniest ones were mostly from executive group members, sometimes in small groups, sometimes in 1:1. They are likely not as funny out of context, but some examples:

  • “bucket for the gator”
  • “The envelope is there to be argued with”
  • “bleep bloop”

I also learnt a couple of fun facts including that Sid cares about the Oxford comma, and that each department has a specific category (such as cars, or animals) for private projects (so would be something like “Project Mustang”, or “Project Duck”).


The CEO shadow program is such a great way to give team members insight into how the company works, while also making the company feel more inclusive, and its top level team members feel more approachable. While I’ve always found Sid to be friendly and down-to-earth, I know that some people are afraid of approaching their manager with something, let alone someone at or near the top. I somewhat jokingly said to someone that it’s a good reminder that our executives are “real” people.

I can’t express how much I’ve appreciated the opportunity and hope that other companies consider a similar program.


Thanks for reading to the end! (Obligatory cute animal picture below)

Thanks to my co-shadows, and the CEO-team team members for their help.

And thanks to Sid for creating the CEO shadow program, and giving us the opportunity!

Author: Cynthia

Technologist, Librarian, Metadata and Technical Services expert, Educator, Mentor, Web Developer, UXer, Accessibility Advocate, Documentarian

Leave a Comment

Please log in using one of these methods to post your comment: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: