A Parable on Leadership & Management

I’m going to share a particularly hilarious story from my life. I’m actually slightly embarrassed to do so even to this day, but there’s a point, especially for those new to management. 

When I was in my very early 30s, maybe just about 30 years old, I had the opportunity to interview for an assistant deanship at a very prestigious law school. Basically to run an admission office of around 10 people at a high profile place with the ensuing pressures that such a spotlight would hold. During the interview process, a wise faculty member asked me about management. I don’t remember the question, but I do remember her ending the question with “…because management is very difficult.”

Now to the embarrassing part — to turn to my internal dialogue in that moment. Which was, and I am not joking, “I was elected the captain of my high school football, track, and baseball teams; there’s nothing difficult about management, that part will be a breeze.”

Let me assure anyone reading of two things.

1. This faculty member was correct, management IS exceptionally hard. And having been elected at age 18 by a bunch of other 18-year-olds to be the captain of anything has zero correlation with the ability to manage people. And it is absurd that I ever thought it did.

2. Just as importantly, leadership and management are different things and require different skill sets. Both important — in fact, both critical — if you want to build or create something wonderful. But different in many ways.

At our firm, there are 31 people who, in theory at least, report directly to me. I say “in theory” not to diminish either them or my role, but because we have been virtual for 10 years and we aren’t a big “meetings culture” place. If you’ve heard of Jason Fried, think of Basecamp and their style. This podcast is an exceptional deep dive into creating a successful and balanced work-life culture through minimized top-down management.

But this in no way means management doesn’t occur. Quite the opposite. It occurs, at our firm, for me, with every decision I make at some strategic level, which is what makes management so challenging. Because it is my responsibility to do my best to not only think about how strategic decisions will impact all 32 people at our firm but also to put myself in the shoes of 31 others. Which, I can assure you, would be challenging for great managers and is exceptionally so for me.

I’m likely not that great of a manager. Because I don’t do this other-person-perspective close to successfully every time. Hopefully, I am a better leader. The concept of leadership, at least, is very simple to me: be the best version of yourself possible and get out of people’s way while empowering them to be the best versions of themselves. But a part of being a leader is to openly embrace your faults and work on them. Day after day. Because, as a leader, a better you results in helping to better those around you.

So, back to management. That’s the challenge. People are exceptionally complex, and knowing their thoughts is not likely possible. But knowing their values is. So, if you want a starting point for managing, I suggest it isn’t where I started many years ago, “Well I was this faux-leader at 18” — but rather, “What is it that the people on my team value?” Put yourself there, and it is a start. But I’ll end on that faculty member’s comment, because the worst thing you can do is to go into management the way I did — it is indeed very difficult.