The Best Leadership Lessons Don't Always Happen in the Office

This weekend I spent hours in my yard tackling projects that were repetitive, physically demanding, and, if I'm being honest, exhausting.

Somewhere between hauling, digging, and wondering why I thought any of this was a good idea, I realized something.

As I worked, I found myself thinking about the many organizations I've had the privilege of serving throughout my career. The work in my yard couldn't have been more different from the work I do every day, but the feeling was familiar. There's something about being the person doing the work that changes your perspective. You notice the little things. You find the inefficiencies. You discover what works, what doesn't, and what looks much easier from the outside than it feels in the moment.

Many of the skills that have served me best throughout my career didn't come from sitting in conference rooms. They came from doing the work.

I've answered customer calls.

I've built spreadsheets at midnight.

I've managed projects.

I've written SOPs.

I've worked with sales teams.

I've supported executives.

I've cleaned up broken processes.

And this weekend, I was reminded what hours of physical labor actually feels like.

Every one of those experiences changed how I lead.

None of those roles existed in isolation. Each one gave me a different perspective on how organizations actually function. I learned what happens when communication breaks down, when systems aren't documented, when responsibilities become unclear, and when well-intentioned processes make work harder instead of easier. Those experiences taught me that every decision made at the leadership level eventually affects someone's day-to-day work.

It's difficult to design a better process if you've never had to follow one.

It's difficult to set realistic expectations if you've never been responsible for delivering them.

It's difficult to earn trust if the people doing the work believe you don't understand what their day actually looks like.

The best operators I've worked with share one thing in common: curiosity and respect. They ask questions before making changes. They spend time understanding the people closest to the work instead of assuming they already know the answers.

That's also why I believe the best consulting doesn't begin with recommendations. It begins with listening. Before suggesting changes, you have to understand the people, the mission, and the realities they're navigating every day. The best solutions are rarely created in isolation, they're built alongside the people who know the work best.

Experience doesn't make someone right.

But lived experience creates empathy. And empathy leads to better decisions.

Experience alone doesn't guarantee wisdom. We've all encountered leaders with years of experience who stopped asking questions long ago. What matters is staying curious enough to keep learning. Lived experience reminds us that every process affects a real person, every system either creates clarity or confusion, and every decision has an impact beyond a spreadsheet or project plan.

Whether you're building technology, managing a nonprofit, leading a sales organization, or running a construction crew, the principle is the same:

The people closest to the work usually have the clearest view of how to improve it.

As leaders, our responsibility isn't to have all the answers. It's to create the kind of environment where people feel comfortable sharing what they're seeing, where good ideas can come from anywhere, and where improvement starts with understanding before action.

Sometimes the best leadership lesson comes from putting on a pair of work gloves instead of opening another PowerPoint.