What a New York City Tour Guide Taught Us About Leadership

Sometimes leadership lessons show up where you least expect them.

Not in a boardroom or a strategy session—but on a tour bus in New York City, led by a guy named Steve from Queens.

We took a trip to NYC with our kids, expecting the usual highlights: great food, iconic sights, a little chaos. What we didn’t expect was that months later, the thing we’d still be talking about—the thing we’d still be quoting—was our tour guide.

Steve.

Within seconds of stepping onto the bus, Steve told us exactly who he was: “I’m from Queens. I’ve got a lawnmower and an above-ground pool.” It didn’t fully make sense, and honestly, it didn’t need to. What it did was give us a clear, immediate sense of him. His personality. His style. His energy.

Let People Know What They Can Expect From You
And that’s where the first leadership lesson shows up—leaders who are clear about who they are make it easier for others to follow them. Too often, leaders skip this step. They assume people will figure them out over time. But what we see again and again in our work is that when leaders don’t define themselves, others fill in the blanks—and not always in ways that help. Your values, your expectations, your leadership philosophy—those shouldn’t be hidden. They should be shared early and often.

The question is simple: what’s your version of “I’m Steve from Queens”?

If You Stand for Something… Actually Stand for It
Later in the trip, standing in Central Park, Steve pointed out something we can’t unsee. There was a musician singing about peace—while actively arguing with another performer over a small patch of space. Steve’s take: “I’ve never seen so many people sing about peace while fighting over a few square feet of concrete.” It was funny, but it also landed a little too close to home.

Because leadership is full of those moments.

It’s easy to talk about values. It’s easy to put words like “collaboration,” “trust,” and “open communication” on a wall. It’s much harder to live them when it counts. When someone challenges your idea. When time is tight. When the stakes are high, that’s where alignment really shows up—or doesn’t. Leaders don’t build credibility through what they say; they build it through what they consistently do. If you stand for something, people are watching to see if you actually stand on it.

Leadership Is Full of Paradoxes (Get Comfortable There)
And then there’s the way Steve gave instructions—something we still quote all the time. “Hurry up, but take your time.” “Help yourself, but don’t be greedy.” At first, it sounds contradictory. But the more you sit with it, the more it sounds like leadership.

Because leadership is full of tension, you’re constantly being asked to hold two things true at the same time. Move quickly, but think carefully. Be confident, but stay open. Push people, but support them. Most people want clarity—they want one right answer. But leadership doesn’t always offer that. Instead, it asks you to operate in the gray space, to navigate nuance without rushing to simplify it.

And if we’re honest, that’s uncomfortable. Our brains don’t love paradox. We want to resolve it, to pick a side, to make things clean and clear. But strong leaders resist that urge. They stay curious. They recognize that more than one perspective can be true at the same time, and they lead from that awareness instead of shutting it down.

There was one more moment from Steve that stuck with us—this one a little more unconventional. As he guided our group through a packed ferry terminal, trying to keep everyone together and on schedule, he gave one very specific instruction: “Walk fast. Don’t make eye contact.”

Now, was this technically about cutting a line? Maybe. But there’s a leadership idea buried in there if you’re willing to look for it.

Not every moment calls for consensus. Not every decision needs to be workshopped or validated by the entire room. Sometimes leadership is about choosing a direction and moving. It’s about having enough clarity and conviction to act, even when it feels uncomfortable. That doesn’t mean ignoring people or dismissing input—but it does mean recognizing when it’s time to stop gathering perspectives and start making progress.

We didn’t expect to come back from New York with leadership lessons. But maybe that’s the point. Leadership isn’t just something you learn in formal settings—it’s something you observe in everyday moments, in how people show up, how they communicate, how they move through the world.

So here’s the question we’ve been sitting with since that trip: what are people learning from you—whether you mean to teach it or not?

Because, like it or not, you’re always leading.
Want to Work on Your Leadership?
If this resonates, you’re exactly the kind of leader we love working with.

At Slingshot25, we help leaders get clear on who they are, what they stand for, and how they show up—especially when it’s hard. Through coaching, training, and real conversations (not just theory), we help you lead in a way that actually sticks.

If you’re ready to do that kind of work, we’d love to talk.
Visit Slingshot25.com or reach out directly—we’re always up for a good leadership conversation.