Leadership Lessons from the DugOut

One of my favorite saying when working with a young hitter is, “Swing hard in case you hit it.” It’s a light-hearted phrase that gets a laugh, but it also carries a deeper truth. I’ve worked with young players for years, and one common habit I notice—especially among those just learning to hit—is the tendency to guide the bat to the ball. Instead of committing fully to the swing, they hold back, unsure if they’ll make contact. Ironically, that hesitation often prevents success. The more they try to control the outcome, the less likely they are to connect.

When I say, “Swing hard in case you hit it,” I’m reminding them to be bold. To commit. To trust the process and give themselves a real chance at success—even if they don’t connect every time.

This idea translates far beyond baseball. In the world of leadership, success often comes from doing exactly that: swinging hard. Taking smart risks. Trying new things. Giving your best effort even when the outcome is uncertain.

Too often, leaders play it safe. They guide their actions cautiously, hoping to avoid mistakes or criticism. But innovation doesn’t come from playing it safe. Growth doesn’t happen in the comfort zone. It happens when you stretch your boundaries, test bold ideas, and learn from what doesn’t work.

Of course, not every risk will pay off. Sometimes, you’ll miss. Sometimes, you’ll strike out. But other times, you’ll connect—and those moments can lead to breakthrough results, deeper trust, and new opportunities. And just like with young hitters, even the misses teach you something that improves your swing next time.

The best leaders I know model this kind of courage. They encourage experimentation. They give their teams permission to take bold swings without fear of failure. They lead with the belief that playing it safe is often the biggest risk of all.

So whether you’re in the batter’s box or the boardroom, the principle holds true: don’t just try to make contact—swing with intent. Swing hard. You just might hit it—and when you do, the result could be something extraordinary.