The Leadership Lessons I Didn’t Learn in Business School

I didn’t learn the most important leadership lessons in a classroom. I am not sure if anyone really does. The lessons that have actually stuck with me have come from showing up in the real world, making mistakes, watching people who did it well, and being honest enough with myself to figure out the difference.

Here is what leadership lessons I’ve learned, and where the best ones came from.

Most people lack direction. Showing up is already half the battle.

This sounds almost too simple to say out loud, but it took me actually meeting people in the world to understand it.

When I was in college, I was struck by how many people didn’t want to do anything. Not just professionally, but in any direction. They weren’t driven. They weren’t trying to get things done. And I realized that just by going out, being present, working hard, and caring, you have already solved most of your competitive problems. Knowledge and experience will come. But just wanting to be there, just being driven, is half the battle.

I always heard that saying. I thought it was kind of overblown until I actually saw what it looked like from the other side.

My dad deserves credit here, too. He didn’t push me to be in the family business. What he did was push me to go do something. Go to work for these people. Go learn the business. If you like it, great. If you don’t, pick something different. But go be useful. Don’t waste your life.

That’s not just a pet peeve for me. It’s more than that. I do not want to waste my life. I want my daughters to know their dad. I want my wife to say I was a great husband. I want to do good in the world. We don’t get another shot at this. That is, it. So, you had better go do something about it.

“Just being driven and wanting to be there is half the battle. I didn’t fully believe that until I actually met people in the world.”

The mistake I made in my first year as president

The one I talk about most honestly is the infamous Australia letter I sent when I first became president of Signarama. When I started, I knew where I wanted to go. I knew the biggest thing we had to do was get everyone onto the same system. That was a contentious conversation internally. I believed in that direction deeply, and I still do. But I went way too hot, way too quick.

I sent a letter to our owners in Australia that was heavy-handed, and it could have been better written. I didn’t fully understand Australian culture yet. I was 25 years old, sitting across from people who had been running their businesses longer than I’d been alive.

The passion behind what I was trying to do was not wrong. The way I did it was, and I ended up causing more pain and more cleanup than I had to. And the leadership lesson I took from that is one I have come back to constantly: seek first to understand, then to be understood. I should have taken months to actually understand our franchise owners before I started moving things. I needed to read the room a lot better than I did.

But here is the other part of it. When you make a mistake like that, you own it. You apologize. You start over. You go back to listening. And then you explain, clearly, not as a corporate mandate but as a real reason why you are doing what you are doing, so you can earn the buy-in you need to move forward.

It was not my first mistake, and it won’t likely be my last. But that one taught me more about leadership than anything I read in a book.

“Seek first to understand, then to be understood. I should have taken months to understand our franchise owners before I started moving things.”

You just have to care

I feel like a marriage counselor sometimes. And I felt that way even before I was married, which probably isn’t a great sign.

But I think everyone is looking for the magic switch, the one thing that will make it all click. And I hear the same thing now with AI, and this idea is that it’s going to solve everything which it’s not and honestly, at some point, you just have to give a damn. The people who care about their business work really hard and genuinely want to be there; do well. The people who are looking for shortcuts, who are just trying to get to Friday, are not going to get there. There are hard parts of every business and every life. You deal with them, and you move forward, but you have to actually care.

The franchise owner who comes to mind when I think about this is Maggie Harlow. She gets brought up all the time, and there is a reason for that. She is always trying to learn the next thing, always trying to understand her staff better, always trying to grow as a manager and as a leader. It is never over for her.

But the thing she does that really shaped how I think about leadership, especially early on, is the way she makes the person across from her feel like the most important person in the room. When I was in my twenties, she called me boss. She wrote me notes. She treated me with more respect than I probably deserved at that point in my career. And she still does it today. I texted her recently and she responded the same way. She has more experience than me. She does not need to do any of that. But she does, because she genuinely cares. And you can tell. You always can.

Writing the book, and what it made real

My wife was pregnant with our first child when I wrote The List, and I’m a person who thinks deeply but also likes to plan and have a structure. So, I had what I would describe as a very organized freak-out about becoming a parent.

What are the lessons I want my kids to know? That question led me back to my own childhood, to what my parents instilled in me, and to how much of that I had taken for granted. A lot of people I grew up with didn’t have that same foundation. And I wanted to build something intentional for my kids.

So, I took the base of what my dad built, and I added and tweaked it to represent what I actually believe and what I want to pass on. And now I do the list with my daughter every morning on the drive to school. She’s four, so she is mostly just mimicking it back to me right now, which is fine. The next phase is going to be, okay, what does this actually mean? Let’s go a little deeper as she gets older, and these ideas start to crystallize and shape her values too.

What the process revealed is that I believe these things more concretely than I realized. Putting values on paper makes them real in a way that just thinking about them never quite does. And it was more vulnerable than I expected, because you are admitting you are a new parent figuring it out as you go. I wanted the book to be a resource for people who never had that kind of foundation, or who want to build it intentionally for the next generation. Whatever values matter to you, you change it. You make it yours.

When skills beat values, it catches up with you

It has happened. Especially in leadership positions. If the role is a specific, defined task and the person just needs to execute on that thing, you can sometimes get away with a values mismatch. But the moment you put someone in front of a room of franchise owners, on a call representing the brand, at a conference where they are carrying your culture, it breaks down fast.

Even if they are incredibly talented, even if they are the smartest person in the room, if people do not want to listen to them, if there is something that just does not feel right, you cannot get past it. You have to earn the right to be heard. And if the values are not there, the talent does not close that gap. Not in this business.

There is no secret sauce

For a long time, I thought successful people had figured out something I hadn’t yet. I would walk into certain rooms in my twenties and assume the people across from me were operating on some other level. Smarter. Further along. With access to something I was still missing.

Over time, I had a moment of realization: they’re just people. Some are brilliant. Some are charismatic. Some have real skills worth admiring. But they are not operating with a secret nobody else has access to.

If you work really hard, keep committing to education and growing yourself, genuinely care, and put people first, you are going to be successful. That is, it. It’s not magic. There are people who are more talented than others, absolutely. But at the end of the day, do you want it? Do you have the drive? Can you do the work?

I kind of psyched myself up for no reason when I was younger, worrying about how I measured up. The answer was simpler than I was making it. It always is.

“If you work really hard, keep learning, genuinely care, and put people first, you are going to be successful. It is not magic. Do you want it? Can you do the work?”

Key Takeaways

Showing up, being driven, and genuinely caring is more of a competitive advantage than most people realize, because a lot of people don’t do it.

Seek first to understand, then to be understood. Moving fast without understanding the room creates more cleanup than the speed was worth.

When you make a mistake, you own it, apologize, and start over. That is leadership.

The people who succeed long-term are the ones who care and never decide it is over. The ones who are looking for shortcuts are not going to get there.

Values mismatches in leadership roles are very hard to overcome with talent alone. Hire for both, but if you have to choose, values wins.

There is no secret sauce. Work hard, keep learning, put people first. That is the whole thing.