Published at https://www.linkedin.com/feed/update/urn:li:linkedInArticle:7096866019285041152/
Hello there. I’m Boomie. In the past few years, I’ve been a Senior Engineering Manager. Along the way, I became interested in expanding my breadth of responsibilities. The week of July 31 2023, I participated in the GitLab Development Director Shadow program. This blog is about my experiences. I’ll discuss why I signed up, highlights from the week, and the impact it had on me.
Summary/TLDR
If you can spend even 20 hours in one week shadowing Wayne Haber, do it. You are an active participant and not just an observer.
I especially recommend this for Engineering leaders or people curious about engineering leadership, but it might be valuable even if you’re not in that category.
And if you’re interested in setting up your own shadow program, you can read Shadow programs give employees a peek into leadership roles | GitLab by Fatima Sarah Khalid.
Development? Engineering?
As the saying goes, “naming things is hard”. I’ve been called a Programmer/Analyst, Coder, Developer, Engineer, Software Engineer, etc. You’ll see that Wayne’s title is “Development Director”. However, since I’ve worked in industries where Development was *not* referring to Software, I will use “Engineering Director” since that title is widely used in the software industry. :-)
Why I Signed Up
When Individual Contributors ask me about being an Engineering Manager, I ask them “why”. I ask to ensure that they are not just viewing it as a promotion and that they would enjoy (or at least not hate) all that management/leadership brings. In the past, management was perceived as a promotion, but it is a different job than engineering, even if you’re still hands-on. Similarly, being a Director is not necessarily the same job as being a Manager.
As I’ve considered my career path, I’ve done informational interviews with those who had jobs as Engineering Directors (and VP of Engineering, but that’s a story for a different discussion/blog). I’ve asked these Directors what a day or week or month in their life was like, what their challenges were, what they liked about the job, and more. When I learned there was an opportunity to shadow one for a week, I jumped at the chance, and added it to my TODO-list. I was actively interviewing so I decided not to sign up until there was a lull in interviews or I was done interviewing - whichever came first.
The job of an Engineering Director differs from company to company. I hoped to see firsthand how it might work, even for just one. What an experience it would be to be in the room, even if virtually. I could then compare it to the notes I’d already made from my informational interviews. Wayne had an opening the following week, so I picked that as my first choice and the open September dates as my second choice.
Before the week started
I signed up on a Wednesday to shadow Wayne the following week. I was finishing up 16+ hours of interviews in a two-week period, along with other job-search tasks, but I was confident I could complete the free GitLab TeamOps training before the shadow week started without using weekend time to do so.
I had a meeting with Wayne and his current shadow. The current shadow (Alejandro Mogollon Medina), who is an open source contributor to GitLab and a GitLab Hero, gave me his views of the program. They were helpful, but I was far from an open source contributor. Wayne asked what I hoped to get from the program, and it seemed like a fit. He asked if I had any questions. I didn’t have many because the shadow description page was pretty informative. He set expectations for the week including letting me know that I could join as many or as few meetings that I was invited to, and work on as many or as few of his projects as I wanted, and didn’t need explanations for if/when I couldn’t attend things.
What excited me about this was that it appeared that I would not just be an observer, I’d be a participant - and that was exactly what the experience was like.
What the week was like
Wayne usually meets with the Shadow before they join any meetings, but because Monday was his early day. I joined two of his meetings beforehand. (My toddler also chose to join, and Wayne switched his avatar to a cartoon. I didn’t get a screenshot of it, but I did post it on LinkedIn.)
To be fully honest, I had not looked at Wayne’s readme page yet, so I initially didn’t know his areas of responsibility. In the first call where I shadowed his meeting with Isaac Dawson working in Security Vulnerability Research, I realized that Wayne was in charge of security products on GitLab - products I had used in my recent job. I heard in this meeting that they were working on reducing the number of false positives in SAST tools, and my eyes lit up. I’ll talk a little bit more about that in the Security section below.
Wayne invited me to as many meetings as he could - roughly 17 meetings. I stayed until they needed to discuss confidential topics. Before I dropped off of any meeting, Wayne always asked if I had questions for him or the other attendees or if they had questions for me. I try to be mindful of people’s time, so I asked group questions publicly but saved a ton of questions to ask Wayne individually.
The meeting with Wayne and his boss, Christopher Lefelhocz, had only confidential items, but Christopher asked about my feedback on the security products. After sharing feedback, the two of them asked if I would be willing to talk to other Engineering Leaders and Product Leaders about my feedback - but of course!
As with GitLab guidelines on all-remote meetings, one of those meetings was livestreamed.
I discuss a few of the trends of the week below.
General
During the week, I shadowed calls with Wayne’s direct reports, peers, boss, stakeholders, mentees, and team. I also shadowed external meetings, such as a non-profit that was interested in having shadow programs of their own.
GitLab defaults to async work. However, since I was free when Wayne was working on his tasks, he invited me to watch along on Zoom, and provide feedback. I did provide feedback but I saved my questions for later to avoid interrupting Wayne’s flow. Following along on Zoom was quite illuminating. I saw how GitLab issues (aka “tickets”) were handled, how OKRs worked, how public handbook pages were updated with internal decisions, how retrospectives were conducted in tickets (more info on retros in this blog), and more. I had also started some updates to GitLab and had errors, and we switched screen share and Wayne helped resolve it.
I participated in a few tickets async. For example, while reviewing some documentation on AI Gateway (part of their AI Architecture), I found a missing image on a public page and added to the comments.
Wayne shared his reading list with me, and I learned how he keeps up with trends in the industry.
I learned how Wayne, who manages a globally distributed all remote team of 83 through 7 direct reports, stays technical and creates focus time for himself.
I learned how they organize their management group. And much more.
I also got to congratulate a few GitLab team members on their recent promotions.
Security & DevSecOps
Once we realized that I had used various GitLab security/DevSecOps features and tools, in addition to the meetings I was already part of, I had the opportunity to talk to Engineering Leaders and Product Leaders about my experiences, and to learn what changes had occurred since I used it, and what features were incoming.
For those interested in more information, some links you can view include Handbook: Sec Section from Development or Handbook: Sec Section from Product, and specifically for SAST, the Direction for SAST.
AI, of course
In what should be no surprise to anyone, GitLab is working on some AI/ML powered features. I got to provide input on the various issues and epics on some of the features. Some of the upcoming features (e.g. explain this vulnerability) will remove some of the pain points I’d experienced with the product. And I learned more information about how the AI working group was formed and is operating.
Mentoring
Wayne clearly is devoted to mentoring others, both within GitLab and outside of GitLab. I was on 3 calls with Wayne and a mentee. In these conversations, after Wayne shared his input, he always asked me for mine. Anyone who knows me knows that I am also very committed to mentoring, so I jumped at the opportunity to provide input and also to learn from the mentees. I am now connected to most of them in case they have further questions or want to meet again.
Impact
I had been unemployed for over 3 months at the time I shadowed. It was nice to feel I was working and contributing, and not only job searching.
I believe in continuous learning. Being honest, I also sometimes struggle with confidence (though not as bad as before). This experience showed me that there were parts of the job that were correct in my mind, and helped confirm the areas where I might have gaps.
Wayne allows shadows to repeat. I might consider another shadow week if there is an opening.
I think I asked Wayne over 30 “meaty” questions during the week. The answers were very insightful and educational and also validating in some cases.
I had to pull myself away from continuing to contribute at the same level after the shadow week ended. But shadow alumni can stay in the slack as long as needed, so I am staying.
The shadow program is not a path to getting a job at GitLab, and the company is a little larger than I was targeting. But I did look at the careers page midway through the shadow week. The experience was a reminder that some of the things I value, such as empathy, can and do exist in companies the size of GitLab.
And I might refer to parts of TeamOps and The GitLab Handbook going forward.
Thanks, Wayne Haber !
