This comes from a real one-on-one I had with my Director of Sales years ago.

We were talking about leadership, and she asked me how I managed. I don’t remember the exact question, but I do remember my answer.

I said:

“Okay, imagine this. You and I both need to drive down to Miami for a retail conference. It’s three days away. Neither of us has ever done the drive before. And remember—this is pre-smartphones. No apps, no Waze telling us about a speed trap 10 km ahead. Just us, a car, and either a paper map or a MapQuest printout.”

She laughed, because yes—this was back when MapQuest was king.

Then I told her what I thought would happen next.

“You’d probably grab your bag, head straight to the car, and start driving south toward Buffalo. At some point, you’d pick up a paper map, figure out the route as you went, and decide along the way where to stop and sleep. You’d make it work.”

Then I contrasted it with my style.

“Me? I’d go back to my office, pull up MapQuest, and print out the whole route to Miami. Then I’d divide the drive into three days, pick the towns I wanted to stop in, and book hotels in advance—because the idea of showing up at midnight hoping there’s a vacancy? Nope. Not happening. Only then would I hit the road.”

She nodded, because he knew I was right about both of us.

And here’s where the leadership lesson came in.

“Look, your approach works for you—you’re comfortable with uncertainty and making decisions on the fly. My approach works for me—I like clarity and structure, so I don’t get distracted worrying about basics like where I’m sleeping. Neither one is better. They’re just different.”

The takeaway?

As a leader, my job isn’t to make you drive the way I would.

My job is to set the destination clearly—Miami, three days from now.

Then I need to trust you to get there your way, and be ready to support you with resources or guidance if you need it.

Because in the end, what matters isn’t whether you used a paper map or a MapQuest printout. What matters is that we both make it to Miami—on time, ready for the conference, and maybe with a few good stories from the road.