When’s the last time you sat at a local youth baseball or softball game?
If it’s been a while, I’d encourage you to do yourself a favor. Carve out an hour this summer. You’ll see young athletes in the making, enjoy reasonably priced concessions—and if you’re paying close attention—you might stumble across a leadership lesson or two.
Catchers or Chasers: Little League Story
This is my 8-year-old grandson’s first year of organized baseball. He played T-ball at 4 and 5, but those games mostly consisted of distracted kids, coaches guiding them to the batter’s box, and a whole lot of missed swings. Progress was measured in small victories—like running the bases in the right direction.
Now that he’s older, the league is more advanced. The kids understand the basic rules, but the reflexes and coordination required to consistently hit or catch a ball are still developing. In other words, there’s more chasing than catching.
The other night, I watched Duke crouch behind the plate in his new catcher’s gear. He looked the part. But over the next hour, he chased far more balls than he caught.
And as I sat there smiling, my mind drifted back to a summer night from my own childhood.
THE LEADERSHIP LESSON: Encouragement vs. Evaluation
I was ten years old, catching in a youth league game under the lights of a warm summer evening. The stands were packed with parents and fans. I was focused, excited, and confident.
“PLAY BALL!” the umpire shouted.
It would’ve been more accurate if he’d yelled, “LET THE PAIN BEGIN!”
I crouched behind home plate, ready for the first pitch from our starting pitcher. He wound up and let it rip—three feet over my head. I never even got a glove on it.
“Ball,” the umpire said simply. I scrambled to the backstop, retrieved it, and lobbed it back.
For the next three innings, the umpire repeated the word “ball” to the point of monotony. Batter after batter stepped to the plate, waited, then watched as pitches sailed high, wide, or fell woefully short. Almost every pitch ended up at or near the same destination—the backstop. I ended up “chasing” more than I was “catching.” It was frustrating.
Finally, after one too many errant pitches and the resulting trip to the backstop, my youthful anger boiled over. I picked up the ball and, in an act of exasperation, hurled it back at my teammate. He was ready and caught my return throw chest high, at his uniform letters. A perfect strike.
“TIME, Ump!”
I looked up and saw Coach Joby heading toward the mound. Finally, I thought, a pitching change. I welcomed it. Anything would be better than this.
As he walked, Coach motioned for me to join him. I trotted out to them.
“Phil, take off your catcher’s gear,” he said calmly.
“Why?” I asked.
“Because you’re gonna pitch.”
Sudden fear seized me. I thought my heart stopped, but then I felt it racing uncontrollably. Breathing was difficult. I was panicked! I had never before pitched. NEVER! Not even in practice. I attempted to remind Coach of this fact.
“Coach, I’ve never pitched before.”
“You won’t be able to say that in a few minutes.”
And with that, the die was cast.
Now my teammate was living my previous catching experience, only worse. Hardly any of my pitches found the strike zone. The majority found the backstop, with a few finding the rib cages of terrified batters. That night, the batter’s box was a danger zone.
A couple of innings later, mercifully, the game ended in a lopsided loss. I was demoralized. I couldn’t look at anyone. All I wanted was to be somewhere else. I pulled my hat down low over my eyes, grabbed my mitt and headed for the exit.
But just then, Coach Joby called me back. Alone with Coach in the dugout, he asked:
In the quiet of the dugout, he looked me in the eye.
“Phil, how did you feel?”
“Terrible,” I admitted.
“Were you trying your best?”
“Yes… but I couldn’t do it.”
He nodded. “You know what? Your teammate was trying his best, too. He couldn’t do it either. But you made him look bad in front of all those people. He’s your teammate. How do you think that made him feel?”
The truth hit me hard. I hadn’t thought about how he felt. I was too busy feeling sorry for myself.
Coach Joby didn’t yell. He didn’t scold. He just reminded me of a leadership lesson I’ve never forgotten:
“Baseball is a team game. Everybody has a part to play. In baseball—and in life—the best players are the ones who care about their teammates.”
I’ve carried that leadership lesson into every boardroom and leadership moment since: Great leaders encourage before they evaluate.
The best leaders never stop learning.
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Extra Innings: Applying the Lesson at Work
The leadership lesson from that dugout is just as relevant in today’s workplace:
- Great leaders don’t look good by making others look bad. Public shaming—whether in a dugout or a staff meeting—says more about your character than theirs.
- Not everyone has the same level of skill or experience. Respect effort, even when the outcome isn’t ideal.
- Before you criticize, ask yourself: Could I do better in their shoes? Empathy is a leadership strength, not a weakness.
- The best leaders share credit and accept responsibility. Poor leaders do the opposite, and their teams know it.
That night, I thought I had failed as both a catcher and a pitcher. But in reality, I had learned something far more valuable: Leadership isn’t about outperforming your teammates—it’s about uplifting them.
Leadership is never about outperforming your teammates—it’s about uplifting them.
3 Practical Ways to Lead with Encouragement Today
What about you?
Is there someone on your team today who needs your encouragement more than your evaluation?
Before you deliver another piece of feedback, consider this: evaluation shapes performance, but encouragement shapes people.
Here are a few ways to lead with encouragement today:
- Catch them doing something right.
Instead of waiting for the mistake, call out the progress, the effort, or the follow-through you might normally overlook. - Ask questions that build, not break.
Try: “What’s working for you right now?” or “Where can I support you?” rather than “Why didn’t you…?” - Be specific with praise.
“Great job” is nice, but “I saw how you handled that tough customer, and I was impressed by your patience” goes further.
Evaluation shapes performance. Encouragement shapes people. The best leaders know when their team needs one—and when they need the other.
Which will define your leadership today?
Gratefully,
Phil
What’s the key leadership lesson from Little League?
Encouragement strengthens teams more than criticism. Great leaders build up teammates instead of tearing them down.
Why does encouragement matter in leadership?
Evaluation shapes performance in the short term. Encouragement builds trust, loyalty, and long-term growth.
How can leaders balance encouragement and evaluation?
Deliver evaluation privately and sparingly. Offer encouragement publicly and consistently.
