Observations from GitLab's Development Director Shadow Program

As an engineer, I believe it's important to understand the priorities of higher-level management. What are their areas of focus, and what types of questions do they typically ask? As engineers, we often spend so much time focusing on details that it can become difficult to see the bigger picture.

I recently had the opportunity to shadow Wayne Haber, Director of Engineering at GitLab, for three days in the GitLab Development Director Shadow program. During this time, I made some observations and takeaways that I hope to apply to my own work in the future and wanted to share my notes.

I have attempted to categorize what I learned into conceptual categories:

Strategic Planning

Wayne emphasized the importance of aligning engineering goals with company objectives, focusing on the purpose of actions and the "why" behind them. Customer purpose and value was a common theme among executives, which contrasted with the technical discussions I usually have as an engineer.

Team Member Allocation

I saw Wayne discussing project priorities and personnel assignments. The decision-making process appeared thorough and considerate, taking into account factors such as choosing the right person for each task.

• There is a job opening that requires the immediate creation of SAST semgrep rules as a core function. Wayne discussed with other stakeholders the best approach to find candidates with a niche skillset.
• Wayne listened to his direct report's requirements during a 1:1 meeting, and provided specific action items with clear details on what needs to be done, when, and what is reasonable.
• Wayne suggested setting a timeframe for transitioning something to someone else during the 1:1. He advised keeping the report flexible but reasonable with the timeline negotiations to help the other person involved realize that the transition is a concrete plan, not just an idea.

Meeting Dynamics

Wayne was skilled at leading meetings, ensuring everyone had a say and the objectives were met.

• Wayne frequently asked for my input and questions, which made me feel included and welcome to consider the stakes of the discussion.
• Wayne balanced giving suggestions with asking for feedback on those suggestions and considering different angles, while still being efficient and avoiding excessive discussion.

Team Dynamics

It was evident that Wayne has a good understanding of the strengths and areas of improvement for each team.

• While reviewing some notes together, he explained his thought process to me when some items seemed insufficient to move forward, indicating a need to determine whether a problem should be considered a technical problem or adaptive problem. I.e. is there a technical reason we are missing the information or is it a people management opportunity?
• We discussed how he upholds the GitLab principle of assuming positive intent and considering the reasons behind others' work.

Mentoring and Coaching

On multiple occasions, Wayne provided guidance to others, offering both strategic advice and tactical solutions.

• It was evident to me that Wayne made an effort to identify career growth opportunities for his direct report that would also benefit the company as a whole. For example, he involved the report in recruitment and hiring activities.

Feedback Reception

I observed Wayne receiving feedback from a previous shadow during a coffee chat. The former shadow shared his perception of his shadowing experience with Wayne from the previous year. Wayne's openness and constructive response to the feedback were commendable.

• The former shadow advised me to observe patterns in communication. He said that Wayne in particular demonstrated active listening and asked good questions. I agree with his assessment!
• To paraphrase Wayne’s response to this feedback, he said success doesn't necessarily come from having great ideas or being skilled at strategizing. It comes from helping teams discover their strengths and excel in them.

Shadowing Wayne has been a valuable experience for me as both an engineer and a GitLab team member, offering a holistic view of engineering leadership. I believe the insights gained will be beneficial for my own professional development.

While my personal schedule only allowed for three days, Wayne offers up to a week for shadowing. I hope to make more time to continue shadowing in the near future and see what else I can learn from it!

I highly recommend anyone with an interest in Engineering Leadership participate in Wayne’s program or one like it. As an engineer, it is insightful to understand the concerns and tradeoffs that are considered at a strategic level in the company. Technical problem-solving is only a portion of the work, and it is important to have a broader understanding of the company's overall goals.

 The GitLab engineering director shadow program is open to both GitLab team members and the general public.  See this page for more information: https://about.gitlab.com/handbook/engineering/development/shadow/director-shadow-program.html