Leadership Lessons from a Terrible Rideshare

Welcome to the Jungle

The car reeked of Taco Bell and cigarette smoke.

I wish that were an exaggeration. But sadly, it’s not.

My colleague Julie and I had just wrapped up a work event and ordered a rideshare to our hotel. We were standing in the thick of a Florida summer – 98 degrees, 100% humidity, zero patience left when our driver came in hot. Literally. He jumped the curb, skidded to a stop, and grunted at me through the window when I confirmed my name.

Things went downhill from there.

We loaded our luggage ourselves (strike one). As soon as we got in, the windows went up, the A/C kicked on, and the smell hit us. It was a special mix – fast food, stale smoke, and something I couldn’t quite place. Probably regret.

That’s when our driver, in a thick Eastern European accent, launched into a story about his recent gastrologist appointment. Between deep pulls on a cigarette and the booming sound of Guns N’ Roses on the radio, he gave us more digestive detail than any human should ever receive from a stranger.

And that was just mile one.

It Gets Worse

Not long into our trip, the car, an electric vehicle, started losing power. The accelerator gave out. “Something’s wrong,” he said. Helpful.

We pulled off the highway, and the driver opened the hood like he was about to summon the spirits of Detroit. Nothing worked. He looked up and told us, “You’ll have to walk. It’s just two miles.”

So we got out, grabbed our bags, and started walking. In Florida. In August.

A few minutes into our sweaty hike, he pulled up next to us. “Car is working now. You vant ride again?” We looked at each other, shrugged, and got back in. What else could go wrong?

Turns out, plenty.

He offered to take us on a detour. “Vould you like to see an alligator?” No, no, we would not. But apparently that wasn’t the right answer, because he took us anyway – off route, off schedule, and off-script.

When we finally arrived at the hotel, he looked back at us and said, “Sorry for bad ride. Can you leave good review?”

And then, as a final twist, Julie got a Facebook friend request from him that afternoon. Creepy, huh?

The Ride Was the Point

It’s a story I now tell with a smile. But it stuck with me because it illustrates something most leaders miss:

You can arrive at your destination and still get it completely wrong.

Technically, the driver got us there. Mission accomplished. But how he did it – his presence, his choices, the experience he created – overshadowed the outcome.

And that’s not just a bad rideshare. That’s a leadership parable.

The Results-Only Trap

We’re taught to focus on results. Outcomes. Finish lines.

And in many workplaces, those things are rewarded above all else. If the job gets done, the “how” is often ignored or worse, dismissed as unimportant.

But if you’ve ever worked for a leader who hit the numbers and broke people in the process, you know the truth:

What you achieve matters.

But how you lead changes everything.

How is what shapes culture.

How is what builds trust.

How is what makes the journey bearable or miserable for the people riding with you.

We’ve All Ridden with That Boss

Think about it.

Ever worked for someone who barked orders, ignored feedback, took credit for wins, and blamed others for losses, but still got promoted?

That’s the business equivalent of our driver.

They hit their goals. They met the KPIs. But they left a trail of burned-out, undervalued people behind them. And then they wondered why no one wanted to work with them again.

That’s why How > What isn’t just a nice idea, it’s the difference between being a leader people trust and one they simply endure.

The Real Leadership Test

The real test of leadership isn’t just whether you arrive. It’s how you bring others along.

Do they feel seen?

Do they feel safe?

Do they grow under your guidance or shrink under your pressure?

It’s easy to talk about vision and strategy. But the daily stuff – the tone in a meeting, the reaction under stress, the unexpected detours and challenges – that’s where your how shows up.

That’s where people decide whether you’re worth following.

Fix the Ride, Not Just the Route

I get it.

You’re trying to get results. You’re navigating pressure from the top, expectations from your team, and probably some doubts in your own head. It’s tempting to put your head down and just focus on the outcome.

But here’s the truth: you can’t lead well if you ignore how you lead.

Your method becomes your message.

Your presence shapes the atmosphere.

And the people with you – your team, your peers, your clients – are taking in way more than you think.

How > What isn’t about perfection. It’s about alignment.

It’s about showing up in a way that reflects your values, not just your to-do list.

You’re Already in the Driver’s Seat

You may not feel like you’re “in charge.” But leadership isn’t just about authority. It’s about influence.

And you have it.

You influence how meetings feel. How people collaborate. How decisions are made. Whether trust is built or broken.

You’re already in the car. You’re already leading something. The question is: What kind of experience are you creating along the way?

Final Stop: Legacy

Here’s what I’ve learned.

No one looks back and says, “I’m so glad we hit the Q3 metrics.”

They say, “I’m grateful for how you treated me.”

“I felt safe on your team.”

“I grew under your leadership.”

“You made it worth showing up.”

That’s the kind of legacy worth driving toward.

So yeah, the destination matters. But don’t forget – the ride is the point.

About the Author

Preston Poore spent 30 years in leadership roles at Fortune 500 companies, including The Coca-Cola Company and The Hershey Company, learning firsthand how character shapes results. He’s served on corporate and nonprofit boards—from the defense industry to higher education—helping leaders grow from the inside out. Preston is the author of How Is Greater Than What: Master the Growth and Leadership Skill Everyone Else Ignores, a field guide for becoming the kind of leader people trust.