Why The Best Leaders Start With A Laugh

Leadership isn’t a joke… but this is hilarious!

Late one evening, when everyone had left the office, a young executive was headed to the elevator when he noticed the CEO with a sheet of paper in his hand staring at the paper shredder. 

“Listen,” the CEO said, “this is an important document, and my secretary has gone for the evening. Do you know how to work this thing?”

“Of course,” the executive said, taking it from his hand. He turned the machine on and slid the paper in.

 “Excellent!” the CEO replied. “I just need one copy.” 

Many years ago, I found myself in the passenger seat of a successful businessman’s truck. 

I shadowed him at a young age and watched him work in his business dealings, phone calls, and negotiations. It was astonishing to watch. 

What made him savvy was not his bravado, his courage, or his intellect. 

This man's strength came from the way he connected and communicated with people.

 I watched him move from meeting to phone call to event. 

Making friends, making deals, and making progress.

I didn’t quite realize it at the time...

But I was getting a masterclass in Leadership Communication. 

He punched in the number on his early 2000s Nokia phone and brought it to his ear. 

“Bill! How are ya?” 

“Oh, fair to Midland. Yourself?” I could hardly hear the muffled voice come through the receiver. 

“If I were doing any better, they’d mistake me for a lawyer!” He cackled. 

The sound of audible laughter came from the receiver. 

“Hey, did you hear about the one with the penguin?” \

“Oh boy…” the man said with a chuckle, knowing what’s coming. "Let me hear it."

“A police officer pulled over an 18-wheeler carrying a trailer. As he’s getting his license and registration, he hears some funny sounds coming from the trailer. He goes to check it out and finds he has over fifty penguins scrambling around the back. 

He asked the driver, ‘Sir, why do you have all these penguins back here?’ 

The driver said, ‘Well they’re my friends. We like to go on journeys together in the truck.’ 

The police officer thought for a minute. ‘Sir, you can’t just have fifty penguins. I’m afraid you’re going to have to take them to the zoo.’ 

The driver nods, then drives off. 

The next day, the police officer notices the same truck with the same trailer and pulls him over. As he walks to the driver’s side, he hears the noises inside the trailer again. 

The police officer gets the driver to roll the window down and says, ‘Sir, I thought I told you to take these penguins to the zoo?’ 

‘I did’ sir, the driver says. ‘We had a great time. Today we’re going to the beach!’” 

I smiled to myself as the man on the other line lost it in laughter. 

He finally collected himself… “What can I help you with today, Daryl?” 

My father did this all too often... 

He would call up friends, business partners, prospects, and before getting down to business, he would ALWAYS share a joke.

He wasn’t wasting people's time… He was strengthening the relationship.

Truth be told, many times they were probably more crude than my 8-10-year-old ears should be hearing. (Let’s call it character building)

But the principle remained: 

Laughter is the gateway to people’s hearts.

Comedy has the power to break down barriers and build up connections. 

If you can make people laugh, you can get them to do just about anything.

(Just keep it ethical, okay?)

Laughter builds relationships. 

Laughter lets our guard down. 

Laughter makes us feel good. 

I believe comedy is one of our greatest tools as leaders. 

Sharing a joke, telling a funny story, or a simple act to make other people laugh can help 

• Build trust

• Lighten tension

• Maybe even seal the deal

Research cited by Harvard Business Review found that leaders with a sense of humor were 27% more motivating, and executives rated as outstanding used humor nearly twice as often as their average peers.

Who doesn’t love a good laugh!? 

One of my goals this year is to be more intentional about making stronger connections with clients, employees, partners, friends, and colleagues. 

And how do I plan to do it? By taking a tip right out of my dad’s playbook. 

Imagine calling up a prospect or firing up a meeting, and instead of rushing straight into business, you share a recent joke you heard. 

It gets you laughing, it lightens the mood, and everything after that flows… effortlessly. 

In a world where everyone is so busy rushing to get to business, slowing down long enough to make someone laugh feels almost… rebellious! 

And here’s the punchline: 

It may change everything about how others view you as a leader.

Before your next meeting, sales call, or difficult conversation, try this:

Spend the first 90 seconds sharing:

• A simple joke

• A funny story

• A self-deprecating moment

 Anything to lighten the mood, get a little laugh, and remind them that… you’re a human.

When leaders learn to make others laugh, they won’t just listen…

They’ll lean in. 

What’s the best joke you’ve heard recently?

Let's Make Moves,

-Chase

Happy New Year! If you are working on goal setting and strategizing with leaders in your school, team, or organization, let's talk about how I can help you develop momentum in 2026! 

Book a call here!