You’re Killin’ Me Smalls! 4 Powerful Leadership Lessons from The Sandlot

My boys love baseball. I tolerate it.

Our little one started t-ball last year and has become obsessed, so naturally The Sandlot is now his favorite movie. He watches it on repeat now. Again, I tolerate it being on pretty much 24/7 at our house.

But the other day it was playing in the background, and I sat down for a second to watch. “This Benny kid”, I thought, “this kid is a real leader”. Then I proceeded to watch the entire rest of the movie tuned in to this realization: there are powerful leadership lessons from The Sandlot.

As I watched, Benny does four things and in a natural progression to help Scotty, aka “Smalls” be a part of the team and get better at baseball. Here are the steps I learned:

Include First. Benny notices Smalls as the new kid in town and invites him to play. He needs one more person to round out the team (inclusion doesn’t have to be all altruistic) and invites him to play. He gives him a better hat and better glove to help him acclimate easier into the team and advocates for him so the other (skeptical) kids will include him. But if Benny is including him, the others will follow. People have to feel safe and included before you can help them grow in confidence and skills.

Nourish Confidence. Poor Smalls hardly knows a baseball from the sun, much less how to throw and catch. Benny puts him in the outfit and realizes this rather quickly. Instead of thinking the kid is a lost cause, he knows he needs to give him a win so he will stick it out and the other kids will accept him.

In my favorite scene, he jogs out of the outfield after Smalls has made a fool of himself and tells him to just hold his glove up in the air and he will do the rest. He jogs back to home plate with bat and ball in hand and shouts, “Smalls, throw it to second!” Benny spits on the ball and launches it into the outfit towards Smalls as Smalls chants “Please catch it, please catch it!” eyes closed and glove up. And Benny’s hit strikes square in the center of Smalls’ glove.

The other kids say, alright, this kid is okay and they go on playing. Smalls moves forward a little more confident because of Benny’s hitting and leadership skills, so that now he can build his own skills.

Build Skills. Just like my boys, Benny LOVES baseball. It is his life. So, naturally they all play a lot, a whole lot, all summer long. This practice helps them all grow in their skills, and as they all improve individually they improve together, Smalls included. You’ve got to build people’s confidence enough for people to be willing to put in the work/practice to be able to build skills.

Mobilize and have your people’s back when things get tough. Like any good movie, a major problem erupts about three quarters of the way in. The kids need a baseball, so Smalls goes and takes a ball out of his stepdad’s office. Little does he realize that it is signed by the best baseball player of all time because he doesn’t know who Babe Ruth is. Smalls crushes his first home run with that ball, over the fence and into the yard of “The Beast” the monster and legend of a dog all the boys are terrified of. Naturally, Smalls panics, and when the other kids realize who signed that ball, they all panic together. How are they going to get it back? They have to.

Benny gets them all together, tells them to calm down, or shows them to calm down because he is calm, and gives out direct instructions on how they are going to handle this offering the next right thing. He doesn’t jump off the deep end with panic and what ifs, he just works the team to do what is needed next.

Benny has Smalls’ back to fix the biggest “pickle” he’s ever been in. He mobilizes the team to help fix the mess.

These leadership lessons from The Sandlot feel eerily similar to leadership lessons at work. Undoubtedly, leading people is going to erupt in some major problems, whether three quarters in or not. When it does, good leaders have already taken the time to include and build confidence and skills, so when the going gets tough, they can get the team going to fix the issue with as little infighting and panic as possible. Which continues to build inclusion, confidence and skills.

How do you build inclusion, confidence and skills in your people? Can you take these leadership lessons from The Sandlot and apply them at work?

At HPC, we are launching coaching moment videos in 2025! Check out the first moment on Nourishing Confidence here!