Leadership Lessons from the DugOut

One of the clearest truths in baseball and softball—especially when it comes to hitting—is that failure is inevitable. Even at the highest levels of the game, success is measured differently. If a Major League Baseball player gets a hit in just one out of every three at-bats, he’s considered elite—Hall of Fame worthy, even. In college baseball, that rate drops to two in five. Younger players may succeed half the time, but even that means failure is just as common as success.

And yet, failure is where the real growth happens.

When players strike out, miss a ground ball, or make an error in the field, they learn. They make adjustments. They become more resilient. Success feels great, but it rarely teaches as deeply or as quickly as failure does. When everything goes perfectly, it usually means the level of difficulty isn’t high enough. To keep growing, players must be tested. The challenge must evolve.

This principle applies just as strongly in leadership and organizational development. Employees and team members grow most when they’re given stretch assignments—challenges that push them beyond their comfort zones and carry a real risk of failure. These are the moments that demand problem-solving, resilience, and innovation. Without that pressure, growth stalls.

That’s why, in leadership training and development programs, we often design games, scenarios, or simulations that are harder than real-life situations. It’s not about frustrating participants—it’s about creating space for learning. When people struggle in a safe environment, they develop strategies, insights, and confidence that carry over into their day-to-day roles.

Leaders should not shield their teams from failure. Instead, they should create environments where people are encouraged to take calculated risks, experiment with new approaches, and learn from what doesn’t go as planned. That’s where growth happens—not just for individuals, but for the entire organization.

The truth is, success is easy to celebrate, but failure is what shapes us. Whether on the field or in the boardroom, the most valuable lessons often come after we’ve missed the mark. If we’re willing to reflect, adapt, and keep going, failure becomes one of our greatest teachers.

So let your people try hard things. Let them fail—and then help them learn. That’s how champions are made.