What an Uber Driver Taught Me About Leadership

A Short Story

An engineer on my team and I shared an Uber ride from Stripe’s SF office to SFO. We had just wrapped up a great onsite at headquarters and were heading back home to Seattle. Our Uber driver seemed like a nice man, probably in his sixties. When we told him about our flights, he mentioned that they were in different terminals. I asked if he could drop us off at both. It was his reaction to that simple request that made me write this post.

He replied: “Of course. Not a problem at all, and even if there was a problem, we would solve it.”

It was not only what he said. It was how he said it. The tone. The confidence. The complete absence of friction. I immediately replied: “I’m hiring. Want to come work with me?”

He laughed. He understood that I did not literally mean it. He told me he was retired and driving Uber mostly to pass the time. Of course, I did not really mean it. At least not literally. But in some way, I did.

The admiration I felt in that moment caught me off guard. When I got home, I spent some time thinking about why that interaction stayed with me. Why did such a small exchange feel so significant?

What Do Managers Care About?

So what was it about his response that made me want to offer him a job?

The best way I can describe it is this: he demonstrated high agency. By that, I mean a proactive, resourceful mindset. It is the instinct to engage with reality, take ownership, and move things forward instead of getting stuck in constraints. My request was trivial. But his response made me feel that I was in good hands. Subconsciously, it told me: you do not need to worry, I’ll figure it out.

As a manager in a demanding industry, at a company with a high bar like Stripe, I often feel like I am walking on the edge. I am constantly scanning for what might go wrong, where things might break, and what curveballs might hit my team and me next. That is part of the job but it is also exhausting. When someone makes you feel that they are both willing and able to carry some of that burden with you, it is powerful.

As a type-A person, I do not leave that mindset at work. I take it with me into daily life. After all, we all take ourselves wherever we go. So when a professional driver made me feel that I was in good hands, I felt myself relax.

That realization taught me something important: this is exactly the kind of behavior I need from people on my team. I need people who help carry the weight of the team’s responsibilities. Not instead of me, but with me.

I do not think this is unique to me. I suspect most managers reading this will recognize the feeling immediately. When I think about my own team, some people already demonstrate this instinct in one form or another. These are often the people managers naturally gravitate toward when something important needs to get done.

But what about everyone else? And beyond that, is high agency the only thing that matters?

What You Don't Do Yourself Will Never Happen

As a cadet in the IDF Officers Training School, I learned many lessons about leadership. Some of the most important came from our platoon commander. He saw himself first and foremost as an educator and he had one mantra that he repeated to us again and again:

“What you don’t do yourself will never happen.”

At first, that sounds strange. Leadership requires delegation, so on the surface it sounds contradictory.

It took me years to understand what he meant. He did not mean that a leader should do everything personally. He meant that if something matters, the leader is responsible for making sure it becomes real.

If I want my team to demonstrate certain behaviors, it is my job to make that happen. I need to teach them, coach them, model those behaviors, and create the conditions for them to practice them.

Yes, some people naturally exhibit the behaviors you want. But most people, even strong people, have gaps. It is my job to help close those gaps and raise the standard of the team. If I do not do that myself, it simply will not happen.

Looking Forward

One of the great things about working with smart, capable people, especially at companies like Stripe, is that if you make a strong case for something, you will usually get cooperation and support.

My team members want the team to succeed at least as much as I do. But first, I need to be clear with myself about which behaviors matter most.

Each manager has their own list. Mine includes high agency, creating clarity through communication, and flagging problems as soon as they appear.

These are not small things. Very few people master all of them. To teach those behaviors, a manager cannot just talk about them, they have to demonstrate them consistently.

More importantly, they have to create opportunities for others to practice them.

That last part is not easy. If I have a critical project, my instinct is often to give it to the person who already shows the exact behaviors needed to drive it successfully.

That is the safest move for the project, but sometimes it is the wrong move for the team.

Sometimes the better move is to give that opportunity to someone who still needs to build those muscles. That is harder in the short term because it creates more work for me. It means closer supervision and a higher risk of course correction.

But in the long term, it creates another person who can carry real weight. That is how teams get stronger and in the end, this is the real job of leadership: not just carrying the weight yourself, but building more people who can carry it with you.