Blog CEO Shadow Takeaways from Jacie
Published on: May 18, 2021
5 min read

CEO Shadow Takeaways from Jacie

Recap of my experience in the CEO Shadow Program.


Hi! I’m Jacie Bandur. I completed GitLab’s CEO Shadow program from 2021-04-26 through 2021-05-07. It was a really enlightening experience. I generally work in Learning and Development and consider myself a lifelong learner. I can’t even explain how much I learned in such a short about of time. I learned a lot about the business. I learned a lot about the product. But learned even more about the importance of iteration in everything we do.

Qualifications to Participate

I wanted to start this off with touching on qualifications to participate in the program.

I am the type of person that has gone through most of my life thinking I’m not qualified for things. I’m not qualified for that job, that promotion, that program. The list goes on and on.

When I saw the CEO Shadow program kick off in 2019, I really wanted to participate. I was a little intimidated. Who wouldn’t be, spending 2 weeks with the CEO of any company? But time passed and all the sudden it was 2021 and I had not taken any steps to participating in the program.

If you are sitting there waiting for someone to tell you that you are qualified to participate in this program, I’m not big on giving “pep talks,” but here’s me telling you - You are qualified for this program. There’s never going to be a good or perfect time to do it. Tell your manager you want to do the CEO Shadow program. Stop waiting. Sign up today.

Note: Take a look at the eligibility section of the CEO Shadow page for more information on signing up.

Pre-Program Tips

There are many things recommended for shadows to do pre-program outlined on the CEO Shadow handbook page. As I was going through the program there were things that I thought helped me (or would have helped me).

Here are my top 6 recommendations:

  1. Make sure your team knows you will be unavailable for 2 weeks. This isn’t a program that can or should be done alongside your normal day to day work. I found catching up from the 2 weeks away kind of difficult because I was trying to keep up on what was going on and I had a bunch of half done things.
  2. Talk with people who have done the shadow program - schedule at least 3 coffee chats with CEO Shadow Alumni.
  3. Have food that is easy to eat quickly. Sid’s meetings are back to back most days, so you will have small amounts of time to eat throughout the day. Sid does eat during calls, which you are welcome to do, too, but if you are taking notes, it is difficult to eat. And this will make you realize why speedy meetings are so important!
  4. Listen to the Executive Leadership LinkedIn Learning course.
  5. Be prepared to ask questions. When doing the program virtually, there isn’t a ton of time for asking questions, so when one would come up, I would add it to a note on my computer and ask if there was ever time with just the shadows and Sid.
  6. Take at least 1 day off after the program. Take even a couple of days off if you can! This is recommended on the handbook page, but I can’t stress this enough.


Group Conversations

I’ve been at GitLab for almost 4 years. When I joined, I made it a point to attend as many GC’s as I could. I had gotten out of the habit of attending Group Conversations. After attending them again for 2 weeks, I realized how important they are to understand better what is going on across the business. Everything in the organization is so intertwined. It’s helpful to understand what other teams are working on and succeeding in.


We should all be giving and receiving feedback often. We have a whole handbook page on giving and receiving feedback. Read the handbook page and watch the videos, as well. Practice giving feedback. I recommend using the 1-1 agenda Sid uses, because Feedback is an essential piece of that agenda, and it makes feedback more of a routine thing.

Biggest Takeaway

We have an incredible team here at GitLab, from Engineering to Product to Sales to People and all the groups in between. There are so many great ideas. I observed the constant reinforcement by Sid to start with something small and build on it. You can ALWAYS make something more complex. It’s hard to go back to something more simple when you start with something complex.

A couple of quotes that I heard from Sid during the program that reinforced this point:

  • “Every complex system evolves from a simple system that worked.”
  • “It’s very clear what is the simple solution. We can always make it more complicated as we go on.”

I know they are very similar, but they happened in different meetings on different days, so the point was reinforced repeatedly.

During the program, I reflected on the projects that I’am working on. How many of them am I trying to do too much on before releasing. Probably all of them. When I’m working on projects in the future, I will break them down into smaller, more doable chunks. Iteration is hard - it’s a skill to be practicing constantly.


Overall, the program was really insightful and impactful. If you haven’t participated in it yet, I cannot encourage you enough to do so!

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