My experience shadowing an Engineering Director for a week
Engineering Leader/Director at Inspire Clean Energy
During the first week of Feb of 2023, I shadowed Wayne Haber, who leads the Secure, Govern, Data Science, and Growth teams at GitLab, for about one week. GitLab is a very open company that not only open sources its core but also publicly lists its operating Handbook and even OKRs. It's also a remote-first company, as outlined by its CEO in its manifesto back in 2015. GitLab has been running shadow programs at different levels and positions, from CEO to CFO to Director. Unsurprisingly these shadow programs are available only to GitLab employees except the one offered by Wayne, who recently opened up his Development Director Shadow Program to external participants if you meet the criteria. Since I knew Wayne from my mentoring sessions earlier, it was relatively easy for me to get into the program. Once accepted, I had to sign an NDA and complete a checklist before my first day. I also reviewed Wayne's Readme to understand his working style and collaborate effectively.
Timeline of the shadow week
On the first day of my shadow week, I set up an intro call with Wayne to understand what the week would look like and what priorities he would focus on. Wayne has extensive experience working in the Security domain, and it's also one of the areas where I am trying to deepen my expertise. So when I saw FedRAMP as one of the priorities, I was interested in how Gitlab is tackling the certification process. He also filled me in on the background of the people I will meet and what issues he is working on with them. He added me to a Slack channel where he would share the topics, issues, and Merge Requests(MR) he is working on. Since I was going to shadow remotely, he added me to most of the meetings, including his 1:1s. Afterward, I followed the sessions and took notes in a shared Google doc of my observations. Sometimes he would also ask me my opinion on how a particular problem could be addressed during a meeting or asynchronously over Slack, making me feel included in the process and engaged in the conversations. Even though Wayne filled me in on any topic I needed more background on, it was still hard to understand the complete picture sometimes, but I did my best in the time I had. At the end of the week, we had a closing call where I provided honest feedback, and he welcomed and appreciated my suggestions for improvements.
Five key observations from the shadow program:
- Like other successful leaders, Wayne also starts with a few key priorities he would like to accomplish for the week in order of importance. Was he able to complete those priorities for my shadow week? You will find that out in the 3rd misconception I address below.
- Wayne is punctual and starts and ends meetings on time. He will end sessions early if there are no other topics to discuss, saving everyone valuable time. He prefers agendas in advance, typically maintained in a shared Google Doc. He and his participants intentionally updated the plan before a meeting, showing the importance of preparedness.
- Wayne seemed inclusive and approachable. He ensures everyone's voices are heard in the meetings and will go around the room to check on everyone and their topics. I found him easy to work with as he promptly responded to my questions over Slack and during meetings.
- Wayne is still technical and knows how to use various specialized tools and services. For example, he quickly used some CURL commands to query the GitLab API for financial auditing.
- Servant leadership shows up in Wayne through his actions as he made my shadow experience very comfortable with good planning and preparation on short notice. He keeps weekly engagements with his direct and skip-level staff to address any issues they may have. Skip-level staff meetings were split by regions (Americas, EMEA, APAC) so that he could dedicate more time per individual.
Misconceptions I had going into the program:
- There will be 30 hours of meetings in a week. In reality, Wayne let me in on about 80% of meetings which ended up being 8 hrs, so he had only about 10-12 hrs of sessions in a week. That shows he keeps plenty of time to do other focused or unplanned work.
- There would be casual conversations, icebreakers, and life check-ins. Wayne is very efficient with his own and others' time. I found a few lighthearted and vulnerable moments in some 1:1s, but apart from that, he seemed focused on work. I provided this feedback to Wayne in our closing meeting, which he appreciated.
- Wayne would complete 80% of his planned priorities. In reality, he was hit by some unplanned work which took about 50% of his time. This work was confidential so I couldn't be part of those meetings due to the sensitivity of the topics. The following week, I learned about some layoffs at GitLab, which might explain the sensitivity of issues, but it's hard to say. In any case that 70% of the non-meeting time would have allowed Wayne to respond to that unplanned but necessary work.
Stats for nerds:
The time I spent actively shadowing in meetings (Sync): ~8 hrs
Number of meetings I shadowed: 14
The total time I spent shadowing (Sync+Async): ~20 hrs
Number of Wayne's direct reports: 4
Number of Wayne’s direct + indirect reports: ~75
Number of MRs (Merge Requests) and issues Wayne interacted with during the shadow week on GitLab: 89
Wayne's busiest day in terms of meetings and MRs: Wednesday
Overall I found my shadowing experience worthwhile, and I highly recommend it to anyone thinking of a career in engineering management who can spare 15-20 hours in a week. I am already thinking of signing up for my 2nd week. You can find more info about Wayne's Director shadow program here.
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Engineering Leader/Director at Inspire Clean Energy
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