The Problem Is the Point

What other sports — and one scouting seminar — reminded me about evaluation, leadership, and growth

The more I think about development — in sports or anywhere else — the more it feels tied to how people approach problems.

One of my favorite things to do is talk with people in other sports about how they evaluate players and build teams. There’s something refreshing about it. When talking to my peers in baseball, walls can go up at some point in the conversation. When conversing with executives in other sports, you often get a real look under the hood — how they think, what they value, where they disagree. It’s fascinating how different teams approach evaluation, how they incorporate subjective and objective information, and what other factors they use to drive decisions. The more I listen, the more I realize how much there is to learn.

So when I had the chance to sit in on fellow UMass Sport Management alum, Dan Hatman, from The Scouting Academy as he led one of his seminars on scouting football players, I was beyond excited.

First and foremost, if you’re involved in football — or looking to break into the game at any level — I’d recommend this class without hesitation. What stood out immediately was Dan’s passion for teaching and his ability to break down the game in a way that challenges how you think about evaluation.

There were plenty of takeaways from the start — not just about scouting, but about the entrepreneurial leap Dan took to build something in a space that didn’t previously exist. He identified a soft spot in the market and built a platform around teaching the craft of evaluation.

But what really grabbed me, given my background, was how he walked through the evaluation of a recent top-five NFL draft pick. The player had elite physical tools but was still learning how to use them on the field. The conversation wasn’t just about traits — it was about understanding the player’s process and how he was learning to solve problems on the field. There were infinite takeaways. A few are listed below, but they only scratch the surface so take the class to learn more.

• The importance of watching “good on good.” How does a player perform against other elite players?

• After your first look, leading with questions rather than rushing to conclusions, which can lead to anchoring bias.

• How good are we, as an organization, at doing what we say we’re going to do as evaluators and developers?

• Do we understand a player’s learning style?

All incredibly important.

But the idea that stuck with me was simpler — and it’s a focal point for me as I prepare for the upcoming MLB season.

Problem-solving.

What problems is the player trying to solve?
How is he navigating them?
And can he handle them consistently — learning from mistakes so he’s better equipped the next time the same problem appears?

In baseball, we talk endlessly about failure and adjustments. But reframing evaluation through the lens of problem-solving sharpens it for me. Tools matter. Metrics matter. But in the end, players face problems on the field that no coach can pause the game to fix. The best ones slow the game down, recognize those problems quickly, and respond in the moment.

As I gear up for the baseball season, this seminar was invigorating. I want to be less drawn to the isolated highlight and more attentive to the decision that preceded it. Less reactive to the mistake and more curious about the adjustments that follow. That feels like a real area of growth in my own evaluation process.

Still, as I think about coaching and the holistic development of the individual, I keep coming back to the idea that this perspective extends far beyond football or baseball.

I often talk with young people trying to break into professional sports. Many have raw ability — intelligence, work ethic, credentials. But I’ve come to realize the separator isn’t talent. It’s their ability to identify soft spots in an organization and position themselves as someone who can solve a real problem.

Where is the friction?
Where is the inefficiency?
Where can you add clarity or value?

That’s how you become indispensable.

For coaches, the question shifts again: What problems are we forcing our players to solve in practice? Do we script drills that prescribe the answers? Or do we create environments where players have to think, adapt, and decide?

At the end of practice, could a player clearly articulate the problems they were forced to solve? Too often, we default to the idea that they “worked hard.” But if they were not forced to solve problems, did they really get better?

I think back to a Middlebury College baseball practice where conditions were intentionally constrained to force decision-making in every phase of the game. It felt chaotic. That was the design. Players had to solve problems in real time.

I also think about one of my mentors. He rarely gives me answers. He asks questions. Sometimes that can be infuriating. But I’m better for it. He forces me to wrestle with the problem rather than feed me the solution.

For parents, this idea manifests differently. What problems do we solve for our kids — and how much room do we give them to struggle through them on their own? (This keeps me up at night!)

At the end of the day, when it comes to leadership, this might be one of our most important responsibilities.

Not to eliminate every problem.
Not to provide every answer.
But to create an environment where people learn how to solve them — because often, the problem is the point.

Because eventually, that’s what separates potential from production — in sports and everywhere else.

The teams — and the people — who experience consistent success aren’t the ones with the fewest problems. They’re the ones who identify them early and don’t hesitate to tackle them.

If the piece resonated, feel free to give it a like or share any thoughts in the comments. I always appreciate the conversation.