Uber CEO Dara Khosrowshahi and the Art of Leading Like a Human

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Borrowed

"The culture of a company is the behavior of its leaders. Leaders get the behavior they exhibit and tolerate."

From "Execution" by Larry Bossidy, Ram Charan, and Charles Burck [Book]

Learned

If you don’t know Dara Khosrowshahi, he’s the CEO of Uber and the guy who took them from losing $3 billion a year to generating nearly $9.8 billion in profit. Before that, he spent 12 years as CEO of Expedia, growing it from a $2.1 billion company to $8.8 billion. He’s one of the most quietly impressive leaders in business right now.

I didn’t know much about Dara myself until a few weeks ago, when I listened to his interview with Steven Bartlett on the Diary of a CEO podcast, and within minutes, I was taking notes and sending clips to Peter and Sei-Wook, Barrel’s co-founders.

I have no idea what it’s like to step into a company the size of Expedia or Uber. But the idea of stepping into a CEO role during a season of change, having to quickly identify core issues and take action, resonated with my experience over the last couple of years at Barrel. Sure, I’d been with the company for over a decade, but in many ways, taking on the role felt like starting anew.

All said, I figured it was worth capturing the takeaways from the discussions. Here are the things I came away with.

CEOs are engineers

Dara studied engineering at Brown, and he thinks like one. His framing: a company is just a machine run by people, and the CEO’s job is to engineer how that machine achieves its goals.

I love this because it strips away the mystique and frames leadership as a design problem. What are the right goals? Where are the failure points? How does information move through the system?

Once you see the decay curve, you can't unsee it

When Dara arrived at Expedia, the company looked fine on the surface. But underneath it all: old technology, coasting leadership, a team living off yesterday’s wins. He described it as the exponential decay curve. Things look okay until they don’t, and by the time it’s obvious, it’s already late. He didn’t hesitate to start making moves. Three months in, his head of HR told him he was scaring people. His response was essentially: I know. Because he’d seen what was coming, and he didn’t have the luxury of moving slowly.

The lesson for me isn’t about being aggressive. It’s about trusting your diagnosis. When you see the real problem, act on it. Don’t wait for more confirmation. This couldn’t feel any more true than it does right now with the rapid development of AI happening before our eyes.

Transparency has to go down to go up

When Dara arrived at Expedia, he came in from the financial side, with years of experience in investment banking and M&A, not leadership. And he learned this lesson the hard way.

If you soften the truth on the way down, your team learns to soften it on the way back up. And now you're making decisions on filtered information. He said the greatest failure mode for a CEO isn't making the wrong decision. It's getting the wrong data that leads to the wrong decision.

So at Expedia, he led with radical honesty downward, in hopes he'd get the same in return. Some people couldn't handle it and left. He was fine with that. In his mind, if someone can't face the truth, they can't surface it either.

He also built channels specifically designed to get around the normal flow, regularly spending time with people four or five levels below him. He found folks who would say what they actually observed and how they actually felt.

Many years ago I learned that when a leader says "my door is always open," it's usually a cop-out. Dara may have said the same thing, but then he went out and found the people who would actually use it. One of the first things I did when I became CEO was conduct one-on-ones with everyone at the company, which evolved into writing a weekly update to the team covering anything and everything from the week.

Barrel is a fraction of the size of Expedia or Uber, so seeing this principle at work from a leader operating at that scale was inspiring, and a reminder not to let that practice fade, no matter how we grow.

How you lose matters as much as how you win

Early in his career, Dara watched his mentor Barry Diller, the legendary media executive, lose a major acquisition bid for Paramount Pictures. PR people scrambled to spin it into something it wasn’t. Barry’s response cut through it all: they won, we lost, next. No BS, no lengthy post-mortem, just honest acknowledgment and forward motion.

Dara carried that with him. Recognize the loss, say it out loud, analyze briefly, then move on. Not glossing over it or obsessing. He put it simply: if you’re not taking shots, you’re not missing.

We have a saying at Barrel: every setback is an opportunity. Easy to put in an onboarding document, harder to actually live. Earlier this year, we lost a large client. They’d only been with us a few months and had a sizable impact on our projections for the year. And I knew that how I communicated it to the team mattered as much as anything else. I could have let the anxiety spread, made it feel bigger and scarier than it needed to be. Instead, I tried to name it clearly, give it its proper weight for reflection, and keep us moving. The lessons were clear, and I knew dwelling wouldn’t help anyone.

Hungry companies build differently

When Uber came calling, it was a mess. Losing billions, managing a rough reputation, and in essence, a company with a lot to prove. Dara left a successful run at Expedia to take it on anyway. And one of the things he’s most proud of preserving as Uber has grown is the "chip on its shoulder," that sense of still having something to prove.

Barrel doesn’t have a chip on its shoulder. But what I think is unique about us is our belief in what we're building, our commitment to putting in the work, and writing our own story, not waiting for some big external event to validate it. I'm biased, but I think it's a special kind of hunger. And this made think about how it's worth protecting as we grow.

As a company scales, the risk is that you start playing defense without realizing it. You have more to lose, so you get careful. Dara’s whole posture is the opposite. The bigger you get, the more shots you can afford to take. Protect the hunger, not the record.

Don't crowdsource culture

"When Dara first came into Uber, he crowdsourced a list of values and got back words like 'passion' and 'teamwork.' It said nothing about Uber. It could've been any company anywhere. The lesson he took: values that come from consensus say nothing. They reflect what everyone can agree on, not what anyone actually believes.

So the second time, he stopped asking and started deciding. The one value he wrote himself, the only one that survived both attempts: 'Do the right thing, period.' No explanation needed. Just: use your judgment, we trust you.

He also made a sharp point about how values go wrong. One of Uber's original values encouraged people to challenge each other honestly. Good in spirit but over time it became an excuse to be unkind. The value wasn't the problem. The way it was lived was. Values have to come from conviction, not consensus. Otherwise they get gamed.

I was thinking about this a lot last year. I had the leadership team read IKEA founder Ingvar Kamprad's "Testament of a Furniture Dealer," a letter he wrote as the company started to scale, outlining why it exists and the values that define the team. It went over well, and I left the discussion wanting to create my own. I wrote it on and off for months. I remember wondering whether I should crowdsource it, run sessions, or ask the team what they thought. But I kept coming back to the same feeling: I already knew. I trusted what I'd observed, the conversations I'd had, and the kind of company I want to build. So I leaned into that. I've been using it for onboarding and recently ran a session with the team. Hearing how much it resonates, and how the team feels it reflects who we are, has been special.

Goals are the hardest part

Dara talked about goal setting, and it's an area I'm always working on. I'm a big believer that it's the daily inputs that create the biggest outcomes over time, and that knowing where you're going matters more than chasing a finish line. That said, I've also seen firsthand how big goals can be inspiring and act as milestones on a much longer journey.

What I appreciated about Dara's take is the honesty. He believes in goals, uses them religiously across every team at Uber, and yet, he admits it's an imperfect system. Goals can be set too high or too low. People can game them. And picking the right ones in the first place is itself the hardest problem. He states it plainly: I wish there was a better one.

So what can we do? Just set the best goals you can, track them honestly, and keep refining.

Leading like a human

When I think about what Dara’s talking about on the whole, it all comes back to one thing: leading like a human. And I think I understand why he leads that way.

Before he ever ran a company, he spent years in investment banking and M&A work. He never managed large teams. Never had a traditional leadership track. When he stepped up for the CEO role at Expedia, he was figuring it out in real time. No playbook, no template, just instinct and honesty and a willingness to learn.

I think that’s exactly why it works. He never picked up the bad habits that come with being groomed for the role. He just did what felt right. Called things as he saw them. Made decisions without hiding behind process. And trusted that if he was straight with people, they’d be straight back.

I can relate to that pretty deeply. I didn’t set out to be a CEO. I grew into it over 13 years at Barrel, learning as I went, making plenty of mistakes along the way. No playbook then, or now.

And there isn't one. You just keep showing up, stay curious, stay honest, protect the hunger, and lead like a human. The fun comes from the feeling that you've never fully figured it out.

"Strive to be human, not a boss."

Julie Zhuo, Making of a Manager

Listen to Dara's interview on Diary of a CEO here.

Also, some related writing:

& Thought

Where am I leading the way I think I'm supposed to, instead of the way I know is right?

Uber CEO Dara Khosrowshahi and the Art of Leading Like a Human

Borrowed