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April 2024
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Leading With a Laugh

Serious talk about workplace humor.

By Caren S. Neile, Ph.D.

Did you hear the one about the CEO who used humor in the office? He paid his employees in yucks instead of bucks!

In the workplace, humor is serious business. Laughter can bring a team together and help employees resolve conflict. But it can also lead to terrible misunderstandings. That doesn’t mean that leaders should be afraid to use it! As with any powerful tool, you’ll want to do so properly.

Leading employees with humor means different things to different people. Maybe it takes the form of sharing jokes with employees or sending along funny videos or cartoons. Maybe it’s infused into the very DNA of the company. In any case, experts agree, it can make all the difference in building and maintaining a successful team.

Why is humor such an important leadership tool? Funny you should ask! Every laugh, writes Alison Beard in the Harvard Business Review, “brings with it a host of business benefits. Laughter relieves stress and boredom, boosts engagement and well-being, and spurs not only creativity and collaboration, but also analytic precision and productivity.” Beard, a senior editor at the Review, points out that her favorite bosses “know how to be funny and elicit the same fun-loving behavior from their employees.”

“My favorite meetings,” she writes, “start with some witty banter—jokes about the latest IT upgrade, a funny story about a difficult author, some gentle ribbing over a missed deadline. My favorite colleagues make me laugh with personal stories, random emails, and occasionally off-color comments.”

Markus Seppälä, DTM, who works in executive compensation, agrees. In fact, says the founding member of the Basel International Speakers in Switzerland, it’s common for senior executives to have a sense of humor.

“You don’t get to the top of the corporate ladder without social skills,” he says, “and humor is an important one.”

Luring in the Laughs

Once you’ve determined that humor is a good idea, how do you proceed? Before you decide to tell a few jokes, determine whether or not the people around you will appreciate them. This is especially true when working in today’s global environment.

“Humor does not always easily or elegantly cross cultural borders,” says Christian Höferle, founder of The Culture Mastery, an Atlanta, Georgia-based organization focused on strategies for closing culture gaps. “What we find funny is often defined by our shared experience in a group, including our cultural and pop-cultural reference points. Say I make what I think is a humorous remark based on a popular TV show or book. It’s going to fall flat if my audience doesn’t share my knowledge.”

Early in his career, Höferle, who is originally from Germany, made a joke to a crowd in Tennessee. The remark was based on his native land’s lax approach to religion—which was vastly different from that of his audience. Needless to say, the joke landed with a very awkward thud. When that happens, speakers may have to work extra hard to regain their rapport with listeners, not to mention their own confidence.

Höferle notes, “Unless you know your audience well, it’s usually best to steer clear of humor about hot-button issues such as religion, as well as politics and sexuality.”

“You don’t get to the top of the corporate ladder without social skills, and humor is an important one.”

—Markus Seppälä, DTM

Knowing the audience is good advice in any speaking situation, of course. And that includes knowledge of the industry you work in. While there may be plenty of dark humor behind the scenes in a funeral parlor, for example, an undertaker probably doesn’t want to joke around with the public, either face-to-face or in marketing! Take your cue from the C-suite, which is to say, the corporate culture. You’re safer when a sense of humor starts at the top, especially if you’re discussing a sensitive matter.

What’s more, you may not always know what kind of day your fellow employees are having. Is someone in the midst of a personal crisis? If so, tread lightly. Always ask yourself: Is comedy what’s called for in this situation?

If humor is on the menu, and you are in a position to inject it into your workplace, here are a few suggestions:

  • Appoint a Minister of Fun. The job title, which can be honorary in addition to other duties, demonstrates that a company is motivated to instill a positive atmosphere. Years ago, a bank based in Miami, Florida, appointed a Minister of Fun. His job description included arranging theme-based parties, funny announcements, and giveaways, and generally encouraging an upbeat workplace culture.
  • Post a joke or cartoon of the day with workplace email or announcements.
  • Take full advantage of April Fool’s Day with a mock newsletter or a funny dress code if appropriate.
  • Try to inject a bit of levity at the beginning and end of business meetings, whether through prepared jokes, cartoons, or light remarks.
  • Consider instituting Comedy Fridays, for which employees are encouraged to dress up in funny ways or post their own jokes. Be sure to include guidelines for taste and sensitivity.
  • Bring in a comedian (vet them carefully!) or humorous speaker for corporate events. You might even bring in a clown who does workshops with adults.
  • Hire an improvisational theater troupe or stand-up comic for a communication workshop. As with any consultant, be sure the professionals you hire have experience working in organizations.

Help! Humor Emergency!

All joking aside, bear in mind that humor can also have a dark side. Think of the words stand-up comics use when discussing their work. They “kill” or “bomb” onstage. They want their audiences “helpless” with laughter to the point that they “die laughing.” While none of these terms is meant to be taken literally, the implication is clear: Humor can be a power game. If your idea of humor is making an employee or group the butt (another negative term!) of jokes, that strategy may very well backfire. In general, it’s a good idea to steer clear of sarcasm or comments that single out a minority.

When in doubt, experts agree, “punch up” rather than down. That is to say, it’s better not to make fun of employees with less power than you, particularly in front of others. That can make you look like a bully, unless they’re definitely in on the joke. There is nothing worse than having your coworkers laugh at you rather than with you. Well, maybe there’s one thing worse: having the boss lead the laughter.


That said, watch what you say about your bosses, too. Instead, try making jokes at your own expense.

The expression “read the room” is useful to keep in mind. Is a coworker truly laughing, or just pretending to enjoy your humor? A true smile can be seen in the crinkles around the eyes, explains Beard. And most of us can spot a fake laugh with both ears tied behind our backs.

In short, genuine humor is not only a great way for a leader to establish trust, but it also should be built on trust. By being authentic, an effective leader connects with employees and draws them in rather than alienating them or making them feel ill at ease.

Humor 101

How do we learn to be funny? In general, says Seppälä, the Swiss Toastmaster, companies looking for assistance with “soft” communication skills for their employees turn to consultants who use aspects of stand-up comedy or improvisational theater techniques to encourage people to be more creative in their jobs. Of the two options, he says, pure stand-up comedy workshops are more challenging, but they can be very useful.

And where do you think Seppälä, who performs stand-up for companies throughout the world, learned to make people laugh?

“Toastmasters definitely helped me develop my sense of humor,” he says. “The way I got into stand-up comedy was that I saw that I was able to make people laugh in my Toastmasters club meetings, especially when that wasn’t the intention. In particular, I noticed this ability when fulfilling leadership roles in club meetings. Without Toastmasters, I would have never gotten into stand-up.”

Genuine humor is not only a great way for a leader to establish trust, but it also should be built on trust.

I’m just not a funny person, you say. Don’t despair. Not everyone was born with the same-size funny bone. You don’t actually need to crack jokes to demonstrate a sense of humor. You can simply encourage others to make them and then share the laugh. After all, comedians love an audience. If you really want to take a stab at being genuinely funny, there are still plenty of ways to do it. For one thing, a lot of humor relies on wordplay. Did someone say “Dad jokes”? Puns are usually a safe bet, as long as you check that everybody gets the joke. (Case in point: Did you understand that in the joke at the start of this article the word “yucks” means “laughs”?) Just don’t be afraid of groans!

Other important elements of humor include extreme exaggeration and the reversal of expectations. Say the office is notoriously freezing. You think your boss is going to show up at work in a winter jacket, but she comes dressed in a parka, ski boots, and snow goggles, instead. Now that’s funny! Or, what about just being silly? Sight gags or pratfalls can also be a safe way to elicit laughter, although pranks in the workplace are best handled with care. Not everyone appreciates them.

You and your team can get into the spirit of humor by making a point to watch funny movies or TV shows or listen to humor podcasts. Or maybe learn a few jokes. Just be sure to practice them well. As they say, the secret of comedy is—wait for it—timing! And what happens if a joke or other humorous attempt falls flat? You could always say something like, “It was a joke, I promise!” or “Back to the drawing board with that one,” or maybe even, “I should probably take some comedy classes after work.”

Come to think of it, that probably wouldn’t be a bad idea.


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