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Development Director Shadow Experiment

Overview video

Overview video

Overview video

What is the Development Director Shadow Experiment?

I got massive value out of participating in our CEO Shadow Program when I did it in July of 2020.

Since then, I have been thinking of doing something similar but smaller in scale. In July of 2021, I asked my teams if they would be interested in remotely shadowing me and several team members expressed interest as they wanted to learn what I do, how I do it, and how I make decisions.

I am experimenting for a couple of months with a smaller scope and smaller-scale shadow program than the CEO Shadow Program. If it goes well, I will continue it and iteratively improve it. If it doesn't go well, I will end it.


For the shadow

For the engineering director

Criteria and process for requesting to be a shadow

  1. I am in the Eastern US (GMT-4). The shadow must be available during some (but not all) of these working hours. Confirm this works for you before proceeding.
  2. You have been with GitLab for at least one month
  3. Check the schedule below for weeks that are Open for shadowing.
  4. Obtain written approval from your manager that they are ok with you participating, as your workload will need to be reduced for the shadow program duration.
  5. Add yourself to the table for the weeks in which you want to shadow via an MR. To get started, you can edit the page here (internal).

How does the shadowing work?

Process for non-shadow meeting attendees

What this program is not

It is not a performance evaluation or a step for a future promotion.

Preparing for the program

  1. Slack me in #wayne_shadow_program to let me know a couple of days before your first shadow
  2. Schedule a coffee chat with me a couple of days before your first shadow (especially if we have not met previously)
  3. Plan to observe and ask questions
  4. Don't plan to do your normal amount of usual work. You should reduce your workload by at least 75% during the shadowing time period.
  5. Participating in the shadow program is a privilege where you may be exposed to confidential information. This is underpinned by trust in the shadows to honor the confidentiality of topics being discussed and information shared. The continuation of this program is entirely dependent on shadows past, present, and future honoring this trust placed in them.
  6. Review my calendar (link TBD)
  7. Review my readme
  8. Re-read GitLab's values prior to your shadow rotation, and be mindful of new and inventive ways that CREDIT is lived out during the meetings you attend.

What to do after you participate

  1. After your shadow completes, I would love to hear feedback on the program, what you learned, what you liked, what you didn't like, feedback on what I can do better, etc.
  2. Consider sharing your learnings with your team and other peers via a blog, slack summary, etc.

Are other directors in engineering also allowing shadows?

No, not at this time.


Week of Shadow
9/20/2021 @warias
9/27/2021 Open
10/4/2021 Open
10/11/2021 Open
10/18/2021 Open
10/25/2021 Open
11/1/2021 Open
11/8/2021 Open
11/15/2021 @mlindsay
11/22/2021 Time off
11/29/2021 Open
12/6/2021 Open
12/13/2021 @mlindsay
12/20/2021 Time off
12/27/2021 Time off
01/03/2022 Open
01/10/2022 Open
01/17/2022 Open
01/24/2022 Open
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