15 tips to succeed at GitLab's CEO Shadow program

Nov 2, 2021 · 4 min read · Leave a comment
Neil McCorrison GitLab profile

You may already know that GitLab offers an incredible thing called the CEO Shadow program where anyone in the company is able to spend time with CEO and co-founder Sid Sijbrandij. It's an opportunity to get a behind-the-scenes look at how our company functions.

There is a lot of information available about the program. But for anyone considering a CEO shadow program, either at GitLab or another company, here are 15 pieces of advice to get the most out of the experience.

1. Take lots of notes

I took copious notes in a separate document because there were so many interesting things that happened - things that I want to remember, follow up on and learn more about. I've heard other shadows have had a notepad handy. Also consider how to further leverage recordings. Even in a normally unrecorded session (like a 1:1), Sid may start a recording to capture fidelity above what notes alone provide. It's an amazing trick.

2. Be open to anything

Sid asked about his presentation energy score, danced the cabbage patch during a 1:1 to celebrate a win, and was able to match everyone's energy in a discussion. So make sure to bring that energy! Also, did you know we have a songbook that everyone can contribute to?

3. Make the most of breaks

Ten-hour days of back-to-back meetings are no joke. Take the time to refresh during the day when you have breaks.

4. You won't be alone

At GitLab, you are one of two active shadows following the "see one, teach one" rotation. Expect to build a great partnership with your co-shadow.

5. Be a good partner

Keep your co-shadow visible in the Zoom gallery view. It’s nice to see body language cues. It’s important to constantly help each other out between note-taking and other tasks.

6. Everyone can benefit from a coach

Sid has a coach to perfect his communication and presentation skills, and others can benefit from one as well. There are lots of resources available to GitLab employees that are highly recommended, including Modern Health.

7. Keep your communications organized

Utilize the sidebar sections feature in Slack. Group the pertinent CEO Shadow channels and team members. You'll want to make sure you stay on top of those messages.

8. Tame your schedule management software

If you have Clockwise installed, it will override your status in Slack and pause notifications (the z indicator). This can mean missing important messages depending on your configuration. You can disable this by running cw settings and pausing the status override.

9. MRs are essential

Yes, everything starts with an MR: Have a concern, idea or suggestion? It’s going to get more traction if you take a stab at drafting it through an MR first.

10. Experiment with your screen layout

Notes on the left or right? Place them at the top of your screen near the camera. It can be easy to sink into taking notes and forget that you are often live on YouTube. Check your video once in a while to check your posture, eye placement and lighting. Don't forget to smile!

11. Time-keeping is important

Use the time-keeping shell script to ensure meetings end on time. It’s amazing, simple and something a lot of shadows continue to use after the program.

12. Don't overthink taking notes

Don’t try to understand context when someone starts talking. Just try to capture what they said accurately. Taking effective notes and having live doc meetings are amazing skills that the shadow program will catapult you into.

13. Listen carefully

Expect to be asked for questions in or following Valley meetings. They are a unique opportunity and another great chance to participate.

14. Early is the new on-time

You should always join a meeting a minute or two before. I found that doing this during the shadow program gave me extra time to chat with participants – and often Sid – before the main meeting started.

15. Get a true glimpse at our core values

You'll see transparency at work. You'll see that our E-group is full of personable, down-to-earth people who thrive on collaboration. You'll hear iteration mentioned - a lot. Not because it's a buzzword, but because it's a highly effective way to develop software.

Sid said it best: "Iteration is one of our super powers. It's super hard to do, but when you get it right, it's super effective. It allows you to innovate quickly."

Join GitLab and become a CEO Shadow yourself!

“How to make the most of a CEO shadow program” – Neil McCorrison

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