Which Bear is Best?

Individual Contributor vs Management Career Tracks

This week I got to chat with a few people that I greatly admire and a lot of our conversations circled around the themes of career satisfaction and the move between individual contributor and manager roles. I have obscured their identifying information but retained the wisdom they shared.

First I went downtown to meet Jen for coffee. Jen manages a team of several hundred, but we first met when she was leading a team of less than a dozen software developers. That was six years ago and since that time I have admired her ascendancy and tried to learn as much from her as possible. For some reason she has taken some interest in my own career and has been a person I turn to for mentorship.

Coincidentally our friend Ned was in the neighborhood and Jen invited him to join us as well. Ned currently does freelance consulting with a billable rate I can only imagine. I had the chance to work with and learn from him earlier in my software developer career. He is one of those people who seems to be extremely good at everything he does.

After catching up a bit, we chatted about management versus individual contributor tracks in engineering. Both Ned and Jen have taken different paths. Ned talked about not being as interested in making box and arrow diagrams as getting into the details inside the boxes. For him, the fun lies in the details.

Jen preferred coaching people and focusing on strategy at a larger scale. One of her current projects is to reframe some expectations at certain levels of the engineering career ladder. For her, people and systems are more interesting than the code itself.

Later that week I got to do a podcast episode with Lea. Lea is a manager of managers in a green energy software company. We first met when we were both learning to code and since then her career trajectory has been astronomic. She posited the interesting exercise of imagining you have a personal assistant. What work would you offload onto this person? The answer to that should signal where some of your unique talents and interests rest.

Finally I got to run with a dear friend who left the world of big tech entirely to pursue art and running. He talked about being burnt out on workplace politics and then also feeling misaligned with company objectives. For him, life is too short to spend time on things you don't genuinely love.

This same week I led two team meetings that have caused me to reflect on which engineering track is best. Many big tech companies have gone through a cycle of layoffs recently and where I work was no different this past week. Coincidentally, a team teach-out I had volunteered to lead was the first team meeting we had after the announcement of layoffs. I took the opportunity to check in with the team and asked everyone to share what their plans were for the weekend to decompress from the tough week of work we were closing.

Later that day we had a scheduled mandatory fun meeting that I was designated to lead. I was hesitant to take on the role of mandatory fun facilitator because I do not want to be perceived as the fun employee. I'm going for more of a ruthlessly efficient and highly competent vibe.

I acquiesced and found myself responsible for a thirty minute social team meeting on a Friday afternoon after a week that included significant layoffs. One move would have been to just cancel the meeting. No one was really in the headspace for an online Pictionary game.

I drew from my past career as an assistant principal of a middle school and randomly matched each teammate with another. I asked everyone to take a few minutes and write down what they appreciate most about getting to work with their assigned coworker. Next we all shared out our appreciations and everyone got to say something nice about a teammate and hear something nice about themselves.

# two shuffles is key.
teammates.shuffle.shuffle.zip(teammates.shuffle.shuffle)

This work felt very fulfilling to me.