Two types of leadership

What kind of leader do I want to be? What makes a good leader? Why do I even want that? Do I even want it?

I ask myself lots of questions like this when I think about my work and where I want to go in the future. And the only sure answer is “It’s complicated.” But since I see everything as a design problem, the first step is always to define the problem, and that means defining what leadership means to me.

Me with my favorite "Like A Boss" mug

This is my favorite mug because it reminds me to do everything LIKE A BOSS.

Two types of leaders

I think that leadership can be broken down into two separate roles: being an executive vs. being a manager.

In my career, I have had opportunities for each. And in my mind, there are a few differences.

Being an executive

An executive is someone who can bring a group of people together and encourage collaboration, thinking big, and amplify everyone’s voices. At work, this often means thinking about the big picture and bringing a sense of strategy to it. It’s about asking the “what if?” questions and defining the horizon, and then asking “how?” and figuring out the best way to get there. It’s about learning who is on your team and what their strengths are, and then putting them in the right direction to run. It involves making hard decisions and tradeoffs to keep everyone going on the path, and sometimes it’s about bailing out of the boat entirely.

Being a manager

A manager is someone who focuses those leadership traits on their people. Again, it’s about learning who is on your team, but it’s more about learning about where their individual paths might lead. It’s about both pushing them along the path when they need it, and giving them a map to explore for themselves. A lot of times it’s about asking questions that don’t have answers, and about teaching people to be curious and self-aware about themselves and their place. As uncomfortable as it is, it also means being the bad guy sometimes and knowing how to give tough love.

Knowing the difference

In my mind, it boils down to leading the work vs. leading the people.

There are people who are skilled at one or the other, and sometimes, you come across people who are skilled at both. To make things more complex, there is the fact that people can be more or less interested in each of these roles.

When it comes to being an executive, having high skill and high desire is a great way to be successful. You know how to solve problems, how to delegate, and how to keep everyone running at peak efficiency. You have to have the discipline and initiative to roll up your sleeves alongside everyone else. You have to be able to admit or pretend that you’re not the smartest person in the room to bring out the best in others. And to be good at all of this, you really have to want it.

But in my experience with great managers, desire is either irrelevant or even counterproductive. Leaders who seek out management for the wrong reasons often end up really bad at it. Since management is about being an advocate and an advisor (and sometimes a therapist), there is a conflict of interest when your own motivation is riding shotgun. If you only want your people to succeed so you can prove your own value, then you are doing them (and yourself) a disservice.

Leading both roles

As a designer, I often feel like I’m not qualified for either role. I always have the “I only went to art school, I have no idea what I’m doing!” impostor in the back of my head. News flash: everybody is just making it up as they go. But I think that design has taught me a few traits that are helpful to succeed at both.

A sense of empathy

No matter which role I’m in, I always believe two things:

  1. Everyone is doing their best. People don’t aim to suck at things, and it’s more productive to interpret their actions in the most generous way possible.
  2. People can only make decisions with the information they have. If they aren’t making good decisions, then they don’t have the right (or enough) information.

Both of these philosophies come from my user experience background. Learning about how people interact with products is an exercise in putting yourself in the shoes of others. And seeking to understand people from a place of grace and good intentions gets you a lot further than assuming the worst until proven otherwise.

A sense of curiosity

Whether you are leading work or people, there is a lot of uncertainty. But the thing that makes you successful is how you approach that uncertainty. Yeah, it’s often scary to admit you don’t have the answers. But as a designer, my job is not to have all the answers. I’m here to figure out how to get to the answers. That means constantly questioning assumptions, digging into the “why?”, and genuinely being curious about the way your people and your product work. It helps a lot if you stay in learning mode as much as possible.

A sense of humility

Speaking of learning, I think this quote is brilliant, even though nobody seems to know who originally said it:

If you’re the smartest person in the room, you’re in the wrong room.

To me, this means that I should never stay in my comfort zone too long. But along with that, I also interpret it as a story of self-awareness and humility: if I am, I better recognize it and pivot pretty quickly. I had better be comfortable with struggling, with failing, and with learning from all of it. I am exited to meet and work with people smarter than me, and content to know that it means I have lots of progress to make.

So what kind of leader am I?

I’m not sure yet. But let’s see how many travel metaphors I have left.

I know I want to be the kind of leader who teaches people, who advocates for people, who inspires people to work together, and who helps light up the dark areas on the map.

I want to be an executive because I know I am good at figuring out how to solve product problems. I’m good at planning out the path and aiming towards the horizon.

I want to be a manager because I am good at connecting with people and at being a cheerleader. I am good at being a North Star, and encouraging people to find their own constellations to follow.

Most of all, I don’t really want to be a manager, but I do think I’d be good at it.