Humor and Leadership: A Funny Combination That Works


When was the last time you laughed at work? When was the last time you made someone else laugh? If you can’t remember, or if it was over a month ago, then you are missing a valuable opportunity to connect with others and frankly, make yourself look better. Humor and leadership may seem like an odd combination, but good leaders know that a timely joke is a powerful tool.

Bringing appropriate fun to serious and not-so-serious situations makes you a formidable force. A study by Harvard Business School found that, “The successful use of humor signals confidence and competence, which in turn increases the joke teller’s status.”

If you take yourself less seriously, people actually take you more seriously.

Many CEOs have told me they see humor as a test to whether they want to work with and be around a person. 

Good leaders aggressively seek out an amusing angle in dealing with others, whether through light humor in a serious situation or the careful use of irony. They know that a person with humor takes the doubt level down a notch and the trust level up.

"If you take yourself less seriously, people actually take you more seriously." @debrabenton. Don't underestimate the power of humor in leadership. Share on X

Why A Sense of Humor Is Important

The most important reason for being good-natured is that it allows you a gentle way to speak difficult truths. If you want to get away with saying what needs to be said, use fitting humor.

One executive coaching client told me, “In my business a sense of humor is not a luxury – it’s a vital organ for survival.”

Humor allows you to connect to others. People like to say that business isn’t personal, but it is personal. All of life is people personally interacting with other people. Work is people interacting with people but with money and title attached to the interactions. Being personal doesn’t mean being inappropriately intimate. You don’t have to start hugging everyone you see (in fact, please don’t).

If you connect on a human level, you more quickly connect on a business one. You can connect human to human, not role to role, more easily with a little humor.

All of life is people personally interacting with other people. Work is people interacting with people but with money and title attached to the interactions. Share on X

Humor and Leadership Can Exist Together

Humor and Leadership Can Exist Together

Humor is being human and personal. It:

  • shows insight into human nature
  • makes life and work more pleasant for you and others
  • creates a relaxed, friendly environment and encourages others to do the same
  • is a great equalizer across barriers of title, position, and role
  • increases your likeability and improves connections
  • saves time in developing affinity
  • mitigates frustration
  • diffuses emotion
  • improves morale
  • lowers blood pressure, yours and others you work with

As one friend put it, “Laughter gives you an instant vacation.” When people feel relaxed and comfortable around you, they’re more likely to trust you.

You should have humor as part of your personal branding – but make sure your humor fits the situation. Choose the right time and place to use suitable, relevant, and brief wittiness. You want to consider your audience and use your humor to connect with them, not demean or alienate them.

Still, if you’re unsure about whether your joke or witty comment will work, just go for it. Good people will be grateful for your attempt to put them at ease.

How to Use Humor In Business

To ratchet up your quick wit, try one of the following: do or say something unexpected, present a paradox, give an anecdote, state an odd fact or outlandish detail, or simply cleverly arrange your words to offer a surprise. One business journal writer took the slogan “What happens in Vegas stays in Vegas” and cleverly titled his blog post, “What Happens in Vagueness Stays in Vagueness.” It was funny and certainly drew in more readers than a less humorous title. 

On the other hand, don’t use sarcastic, corny, or slapstick humor. You’ll either come across as demeaning or silly. You don’t want to generate laughter by flushing the toilet on a conference call either. (But if that happens, accept it with good grace and don’t be a grinch.)

Light self-deprecating humor is good because it doesn’t offend anyone. It’s also an offensive move because it prevents someone else from throwing the first punch at you. Self-deprecating is okay, but never deprecate others. Also, don’t overdo your self-deprecating as this may signal a low self-esteem or other undesirable traits.

Your wit doesn’t have to make others chortle, or generate the kind of laugh that makes them have to cross their legs, but it’s good to at least cause a gentle smile. If you make your conversation or messages boring from a lack of good cheer you will not be first choice or taken as a serious and powerful contender.

Humor Can Be Risky Business

Humor Can Be Risky Business

There is a risk in using humor. Every once in a while, your attempt at levity will fall flat. Sometimes you don’t express the funny side well, or whomever you’re speaking to may have his mind elsewhere and be caught off guard. 

It’s also possible you just weren’t that amusing. Your attempt might have been too esoteric, sardonic, sarcastic, mean, nasty, bizarre, or just not understood and people will not laugh out loud. If your joke offends someone, apologize and seek to rebuild the connection. 

Do not let past misjudgments inhibit you from trying better the next time. Rethink your choice of levity, but do not stop the use of it. 

You Will Not Succeed Without A Sense Of Humor

You probably won’t have perfectly executed humor all the time, but if you never use it, you’ll miss out on connection and possibly promotion. It’s like asking for a raise or a sale. Sometime you fall flat on your face, but you’re not going to get anywhere without trying.

A C-suite executive who lost favor with the CEO was described as, “He talks too fast, doesn’t smile enough, and has no sense of humor.” Now there were other factors that led to his downfall, but that was the sentence said to the board.

Sometimes having good-natured humor is more important than the right answer, decision, approach, look, or response. You’re working with people after all, and they want to relate to you as a person. Being humorous shows your human side, puts people at ease, and builds stronger connections with those around you, all of which makes you a better leader and a more promotable employee.

So crack a smile, tell a joke, and sharpen that wit, because a little bit of funny is good for business.

If you’d like help developing your leadership style, contact me about a long-term coaching relationship or book me for a Bite-Size Executive Coaching session today.

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