Funny Leaders are Better

Lindley Hamilton is a leader who is funny

Once Abraham Lincoln was giving a speech when he was interrupted. “You’re two-faced!” a heckler yelled from the crowd. Lincoln responded, “if I had two faces, do you really think that I’d choose to wear this one?” Lincoln understood that using humor could disarm his enemies.

Leaders with a sense of humor are perceived as 27% more admired and motivating than leaders who don’t crack a joke. Their teams are more likely to solve a creativity challenge and 15% more engaged. A dad joke can help you get paid. So when you’re trying to close the deal, tell your counterpart “My final offer is X and I’ll throw in my pet frog.” Adding that lighthearted line at the end of a sales pitch can increase customers’ willingness to pay by 18%, according to multiple studies.

Humor can even help you land your dream job. In a survey of more than 700 CEOs, 98% of them prefer job applicants with a sense of humor and 84% think that somebody with a sense of humor does better work. Dwight Eisenhower said, “A sense of humor is part of the art of leadership, of getting along with people, of getting things done.” If the guy that defeated the Nazis and built the Interstate Highway system can be funny, then so can you.

Harvard Business School’s research revealed that placing a pun at the end of recommendations for visiting Switzerland (“the flag is a big plus”) made people think the author was more confident, competent, and 37% higher in status than the unpunny version. The flag-joke person was more likely to be chosen as the group leader. But there are limits to how much talent people give you for being funny. No one is putting Jerry Seinfeld in charge of vaccine delivery. But maybe if the vaccine delivery guy was a little funnier, we’d be out of this Covid mess by now? I don’t know. I’m bad at interpreting studies.

Why you think you can’t be funny at work

We’ve created a legend that being professional means not being funny. That, and other myths are far too prevalent in our workplaces. There are four main myths about humor at work.

  • The first is the “serious business” legend, which is the idea that levity cheapens your work. You can come off as not taking your job seriously if you’re joking around. This is not true. Managers with a sense of humor are more motivating and admired. Their employees are more engaged. We reap tremendous rewards for the investment in humor.

If you create an atmosphere where there’s no reason to be afraid of making a joke, your culture loosens up. It’s okay to fail and experiment. Workers don’t want their work to be boring. You are in the flow when you watch for humor. You must be present. You must listen, notice what’s happening, and think about the feelings of others.

How to get funnier

Even if you’re a businessperson who unironically uses terms such as “paradigm shift,” “synergy,” and “it is what it is,” you can still move the needle on your humor skill set. First, get good at self-deprecating, which is the reverse of everything you’ve ever done. Self-deprecation builds bonds with workers, humanizes leaders, and makes others believe that the self-deprecator is more important than she is. (If she can bear to mock herself, she must be convinced in her skills!) It also indicates that workers are allowed to be funny.

If you want to get funnier, start watching stand up comedy. You’ll notice that good comedians have a clear point of view. That’s an essential part of being funny. You must find what works best for your personality. Comedians tend to see the funny side of everyday life. Use similar observations with your coworkers. You can also learn some simple jokes. There is a lot of material on the internet. Don’t give up if people aren’t laughing. Keep refining your style until you get a good reaction. Laugh more, especially at yourself. If you are smiling and happy, then humor will naturally flow through you.

When jokes hurt

If you are in management, you should avoid jokes that are combative (mocking, roasts, teasing). This is why Don Rickles never held an office job. As a manager, use humor to highlight common enemies or shared viewpoints. An “enemy” can be as benign as the expense management system at your company. Everyone should avoid jokes about who people are. Instead, focus your jokes on what people do.

Never punch down by making an employee the butt of your joke. Instead, punch yourself. Once, the head of marketing communications at Apple deliberately arrived late to a meeting. He then had a coworker show video footage of him asking the popular janitor for guidance on how to manage the company. She slapped him in the face and told him to get a grip.

“It was just a joke,” is the last refuge of scoundrels. If you overhear a supposed joke that makes an employee or a protected class a butt of a joke, then you need a strategy to stop it. Say something like, “Please don’t say things like that to other people or me. That’s unsettling.” When someone inevitably claims that he is “just joking” you can respond, “Good, then this won’t be a big deal to end” or “Joking or not, I don’t want to hear things like that.”


Ninety-one percent of executives believe a sense of humor is important for career advancement, while 84% think that employees with a good sense of humor do a better job, according to a study by Robert Half. People who take themselves too seriously in the workplace are usually taken less seriously by others. That reminds me of the joke about the humorless coworker who worked for a promotion. He didn’t get it.

Employees who use humor at work are not flippant or frivolous. Instead, they are behavioral change agents who seek to build a more authentic, engaging, and natural culture. They are among the most emotionally intelligent people in the workplace. They tend to be genuinely well-adjusted, happy, and successful in their work. And that’s not to be laughed at.

As originally published in the Hammer Blog at

Hamilton Lindley is a father, husband, and entrepreneur in Waco. He likes leading by enthusiasm, energy, and empathy.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store