The Dumb Guy

My goal is to be the dumbest guy in the room.

When I first joined the software business in my 20’s, I thought I was pretty smart. My bosses all told me I was smart. I got promoted because I was smart and I did smart things. I thought my path to success was to always be the smartest guy in the room.

Then I grew up.

Over time, I realized some really hard truths. First, there is always someone smarter and someone who is willing to work harder than you. Just being smart isn’t going to get it done. You need focus, commitment, experience. You need to learn from the amazing people around you. You need to have a learning mindset. There is always something you can learn.

Second, it turns out that if you are the smart one, it’s on you. Anything goes wrong? You get the call. System is broken? Your problem. Boss is pissed off? All heads to turn to you.

So, you work harder. You focus more. You study.

And…. you get more work. Your reward for solving impossible problems is to be assigned more impossible problems.

It took me a while, but I figured out this was not a sustainable path.

Why didn’t the other people around me take up the slack? Why was it on me? It seems obvious in retrospect, but it was because I had worked really hard to convince my bosses that I was the only one who could do it. I was indispensable. I was also getting completely burned out.

What if I invested in making the people around me better at their jobs? I could train them and help them understand what I knew and thus, they could help me more. And then, I discovered servant leadership.

The idea behind servant leadership is that the leader of a team is ultimately only there to raise up those around them. By focusing on making others great, they make themselves more successful because the team gets more done at a higher level of quality. It’s not only the right thing to do, but it is in your own self interest.

Looking back on my career, I realized that the people I respected as managers all had that trait. They all sought to make me better. As a result, I worked even harder because I didn’t want to let them down. Managers who just piled work on my desk with no support didn’t get my full support because they clearly didn’t care about me. Why should I care about them?

So, I changed my focus.

I invested in those around me. I tried to figure out how to make them better.

This changed everything. As a manager, I had a strong team around me. They were able to handle things. My workload decreased. More work got done. Quality improved. Here is the punchline: I was no longer the smartest guy in the room.

And I absolutely loved it.

Ideally, everyone who works for me would be way smarter than I am. That is to say, I would become the dumbest guy in the room. Not because I got dumber, but because I surrounded myself with smarter people. Wouldn’t that be amazing? Of course, not everyone you hire works out. You still have to manage people. Some rise to the occasion, some do not. But, your focus needs to be either help them improve or get them out. The worst case is if you just accept mediocre performance. That demotivates the team and results in a worse outcome for you.

The sad thing is that many leaders I have worked with never made this transition successfully.

As a Senior Director of PM, it’s pretty normal for me to have conversations with PMs who want to get promoted. Many of them will tell me that they want to be a “Group Product Manager” which is commonly the first step in PM management. Sadly, when I ask them why they want to manage PM’s, they don’t really have an answer. They are seeking promotion and this is the only goal. Get promoted because you need to climb the ladder. More money, more responsibility, etc.. Just what we are all supposed to want.

And if you look around at the very sorry state of PM leadership in our industry, this actually explains quite a bit. I firmly believe that most people who become senior leaders in PM organizations have zero interest in developing the PM’s working for them. More than once I’ve asked a PM who is new to my PM what their career goals are only to have them respond that nobody has ever asked them this very basic question. Many senior PM’s have never had a single career development discussion with any manager they’ve ever had. While I know this is a problem in the industry, it still shocks me every time.

Watching managers like this get promoted just makes me sad. They have no idea how to make others great, and worse they don’t seem to really care. In their minds, the purpose of the people working for them is to support their ambition. There is no obligation the other way: to raise up those in their org.

And the results show it. These teams typically underperform, the products are just so-so, nobody takes risks, nobody puts in the extra effort. It’s just a job for them, why lean in?

The really ironic part of all this is that for a Product Manager, leadership is probably the most important skillset you can have. And it’s also the most difficult to teach. I can tell you what leadership is, but I can’t teach you to be a leader. You have to…. Well… lead.

Not super helpful.

But, I can tell you how to serve others, which is the gateway drug to leadership.

If you look around you, ask what value you have to the larger team. Are there things you are good at that they struggle with? Are there areas of improvement that you can support? Do you know people who could mentor them? Can you connect them to resources to help them? Every time you do a 1:1 with your subordinates, start with a simple question: “What can I do this week to help you be more successful?”

If you do those things, you are well on your way to becoming a leader.