Year five - Reflections on leadership

A reflection on five years of various forms of management
management
leadership
life
Published

October 18, 2021

I have now been leading teams for over five years in various capacities. The composition of those teams has varied over the years, and the mission and goals change, but increasingly I find myself reflecting on lessons that transcend context and inform any situation where a group of individuals needs to come together to achieve a common goal. Below are a few themes and tactics that I have accumulated within my leadership toolkit although this certainly is not a comprehensive list.

The narrative matters

Humans are literary by nature. We are captivated by story and moved by metaphor and theme. Stories move us and compell us to draw connections between seemingly unrelated topics. People love to place ourselves on an epic stage as actors in some greater play. It is surprising then that storytelling and narrative building isn’t a commonly identified theme when describing leaders in a professional context. We talk a lot about “tactics”; endlessly analyze organizational structures, and spend whole days learning how to run effective 1:1’s with our team members. I would posit that the ability to artfully craft a narrative is a far more powerful and generic skill than many other closely held management and leadership best practices.

Let me make this a bit more concrete. I once taught high school statistics in an inner city school. I started out the year teaching the subject in a very academic fashion, because that’s how I enjoyed learning the subject. We spent weeks on the law of large numbers, the central limit theorem, applying the t-test. It was an abject failure. I’m pretty sure no one learned anything. It was a depressing experience for both me and the students. After some reflection I had the realization that while I was very invested in statistics (it was my job to teach it) for these kids, this was just another class. So I switched strategies.

I decided we would have a casino night. Students would dress up, there would be card games and other games of chance. It was going to be a whole shebang: Vegas for a night. The only criteria for attending casino night was that you would have to design your own casino game, and submit a written report that proved using either experimental data or theoretical derivations that your game of chance put the odds in favor of the house. I was changing the narrative around statistics class. With the announcement of casino night my class had overnight transformed from a snooze fest into a class that was abuzz with activity. Learning stats was tied to the excitement of the night, and everyone was talking about it. Some might say that this wasn’t switching the narrative, it was switching the incentive. I would actually argue that they are the same in this case. Humans in general are motivated by the why as much as we are motivated by the what. For a group of high schoolers, the narrative of getting fancy and spending a “night in Vegas” with their friends was a powerful change of perspective that had an incredibly transformative impact on the amount of learning that was occuring in my classroom.

The tongue has the power of life and death

I once worked at an early stage start up where I spent the better part of a few weeks rearchitecting how the company measured growth. My work drew on a few clever ideas I had read up on after hours, purely becuase I was interested and excited about the opportunity. When I presented my work to my manager, I got a blank stare and she told me she didn’t think it was worth pursuing, she was in a hurry, we could discuss it later. Needless to say I didn’t go home that night to hack away at work related items. My only point here is that whether or not my idea was good, my manager’s approach to collaborating with me was detrimental to the motivation and confidence I had in my work moving forward. I wasn’t inclined to put in more work, or to bring new ideas to her. Part of your job as a leader and a manager is to grow the curiosity, excitement, and fervor of your team. This ties back to narrative: as a leader I am responsible for cultivating the narratve within each of my employees that they are capable, creative, autonomous, and generally awesome.

Proverbs 18:21 says: “The tongue has the power of life and death”. This is absolutely true, and I firmly believe this is a cornerstone of developing and leading high performing teams. Case in point: casino night. Part of the night was “business” focused. We had to do the marketing, organization, financing for the night. So rather than doing it myself I had students interview for the jobs. I mentored and gave advice on the jobs, but mostly I advocated for them, reiterated their strengths, and gave them positive affirmation. The night was an unmitigated success. I still remember the marketing posters that were hung up in the boys bathroom urinals– hilarious and incredibly effective. I would have never thought of the idea.

Lead from the trenches when necessary

Leading teams can get dirty. Inevitably there will be times when the pressure is on, or when things go sideways. Sometimes it will be your team’s fault, and sometimes it won’t. It honestly doesn’t matter. I’ve found that these are the moments when you can instill an incredible amount of trust and loyalty in a short period of time. This requires two things. First, you need to “lead from the trenches”. In other words you need to jump in to the dirty work your team is slogging through, and dig harder and faster than anyone. Second, you need to resolve that no matter how the incident ends, ultimate responsibility lies on your shoulders. Taking full responsibility for any fallout is is an incredibly important part of allowing your team to take risks that have a potentially high payout.

I’ll admit this is partly a matter of leadership style. George Patton vs Dwight Eisenhower. You can be effective without leading from the trenches, but personally I have found this form of servant leadership to play to my strengths.

Make time to plant seeds

When you first start leading technical teams it’s easy to let the organizational and interpersonal portions of the job entirely crowd out the technical portions of your job. This isn’t necessarily a bad thing, the technical skills that often make you stand out as a technical contributor are a necessary but not sufficient condition for your success as a manager and leader. However, as a technical leader I found one of my core contributions is identifying creative opportunities for applying technology to business problems. As I became more proficient at the managerial portions of the job, I started to look for ways to flex some of my time back into the technical realm. My strategy for doing this was to “plant seeds” and to give them up early. To be more concrete: I would look for high impact projects that I could get off the ground using a “20% time” strategy, and once they hit viability/momentum I would aggressively offload those project to members of my team to extend and harden. In doing this it was important to choose projects that had flexible timelines- mission critical product features were strictly off limits, but this had the benefit of allowing me to focus on less critical but potentially more strategic long term initiatives. This strategy likely doesn’t work for all levels of management. If you are C-suite you probably won’t be doing much technical work. However, the strategy to date has worked well for me.