Leadership Lessons from the DugOut

Mike Tyson once said, “Everyone has a plan until they get punched in the face.” As blunt as it sounds, there’s truth in that statement—especially for coaches and leaders. Planning is essential. But adaptability is what separates those who lead well under pressure from those who simply hope for ideal conditions.

Every coach, manager, or team leader starts with a plan. Whether it’s a game strategy, a quarterly business goal, or a meticulously organized event, we map out what we expect to happen. But then, something changes. Something unexpected happens—something that “punches you in the face”—and your plan is no longer viable.

As a baseball coach, I always enter a game with a clear pitching plan. Who’s starting, how many innings they’ll go, who’s coming in for relief—it’s all lined up. But then, the pitcher I expected to last three or four innings walks six batters in the first. Suddenly, we’re scrambling for replacements, rethinking strategy on the fly, and piecing together innings however we can. The plan just took a punch.

The same thing happens in the corporate world. I once helped plan plan an annual leadership meeting for over 1,200 managers. Weeks of logistics, scheduling, materials, and facilitator coordination had gone into it. Then—an ice storm. Only a third of our participants could make it. Some of our facilitators and key presenters were stranded. Printed materials didn’t arrive. It was another unexpected blow. In both cases, the solution wasn’t to cancel. It was to regroup. In the baseball game, we found a way to mix and match pitchers, adjusting our expectations in real time. At the leadership meeting, we leaned into flexibility—reworking group sizes, adapting activities, and getting creative with what we had. Was it perfect? No. Was it effective? Absolutely.

Leaders don’t earn trust by how they perform when everything goes to plan. They earn it by how they respond when nothing does. When the unexpected happens—and it always will—the best leaders stay composed, act decisively, and find ways to move forward.

So yes, Mike Tyson was right. You will get hit in the face. The question is: how will you respond when you do?