Leadership Lessons from the DugOut

A few months ago, I attended a baseball and softball coaching conference. During one of the sessions, the presenter was talking about the evolution of catching, and teaching hitters when he paused and said something that has stuck with me ever since:

“Just remember, there are no always and never’s in baseball.”

The more I thought about it, the more I realized that statement applies just as much to leadership as it does to sports.

As coaches, we love absolutes. We tell players to always get in front of a ground ball. Always catch a fly ball with one hand. Never swing at the first pitch. These phrases are easy to remember, easy to teach, and often rooted in good fundamentals.

The problem is they aren’t always right.

If you’re charging a slow roller, trying to get directly in front of the ball may actually increase the chance of a bad hop or bobble. If you’re sprinting after a fly ball, insisting on catching it with one hand may be more difficult than securing it with two. And while waiting for a good pitch is usually smart, sometimes the first pitch is the best one you’ll see all at-bat. Letting it go because of an “always” rule can cost you.

Great players learn the fundamentals. Elite players learn when to adapt them.

Leadership is no different.

Business is full of advice that sounds absolute. Always celebrate accomplishments publicly. Never criticize an employee in front of others. Never micromanage. Data doesn’t lie.

There’s wisdom in each of those statements, but none of them should be treated as universal laws.

Some employees thrive when recognized in front of their peers. Others would rather disappear into the background. Public recognition that motivates one person may embarrass another.

We’ve all heard that public criticism is bad leadership, and in most situations, it is. But imagine a serious safety violation that puts others at immediate risk. Addressing it in the moment—professionally, respectfully, and with the goal of protecting the team—may be exactly what’s needed.

Even micromanagement, one of leadership’s biggest taboos, has its place. A brand-new employee learning a critical process or someone struggling in a high-risk role may need much more direction and oversight than a seasoned, high-performing team member.

The lesson isn’t that the common advice is wrong. Often it is good advice.

The lesson is that leadership, like baseball, is about judgment.

The best coaches don’t simply teach rules. They teach players how to recognize the situation in front of them. The best leaders do the same. They understand principles, but they also know when the situation calls for flexibility.

So be careful with the “always” and “never” statements. They make great teaching tools, but they rarely tell the whole story.

Because in baseball—and in leadership—the best decisions are almost always situational.