Most leaders I’ve worked with (including some who are flat-out hilarious behind the scenes) have been reluctant to use humor in their public pronouncements.
Honestly, this reticence is understandable. Attempts at humor do backfire, sometimes spectacularly. Here in the UK, one of the most infamous casualties was jewelry tycoon Gerald Ratner, who memorably described his company’s products as “total crap” with a useful shelf-life comparable to that of a “prawn sandwich.”
The result? Ratner found himself out of a job. £500 million was wiped off his company’s share price.
Yikes. But examples like this stand out precisely because they’re rare. On the flip side, there’s good evidence that using humor deftly can make leaders more effective. Among other things, it can humanize them, earn greater trust from employees, build team cohesion, stimulate creativity, smooth change management, and ultimately boost productivity.
If, like me, you think the upsides of humor outweigh the risks, here are a few tips, starting with one that could well have saved the jocular jeweler.
(1) Pick Your Target
Don’t: Punch down. Ratner’s remarks didn’t just denigrate his products. They insulted his consumers, largely working-class families looking for affordable luxury. No wonder they seemed so mean-spirited.
Do: Punch yourself. Humor doesn’t have to have a target, but when it does, the best one to pick on is yourself. Think of Virgin Atlantic founder Richard Branson’s quip, “If you want to be a millionaire, start with a billion dollars and launch a new airline.”
(2) Keep Your Day Job
Don’t: Try to be a standup comedian. Your goal should be occasional, light humor, not a steady stream of edgy jokes. Travis Kalanick, the disgraced former CEO of Uber, attracted a reputation for constant flippancy. It wasn’t the worst thing he (allegedly) did, but it did apparently contribute to Kalanick’s eventual ejection.
Do: Use humor as seasoning. As the quotes above suggest, a single zinger is worth a thousand shaggy-dog stories. This is especially true when the quip encapsulates a deeper truth. Warren Buffett is a master of this art, as suggested by his dictum that “Wall Street is the only place that people ride to in a Rolls Royce to get advice from those who take the subway.”
(3) Take It in Stride
Don’t: Get flustered if they don’t laugh. Humor is hard to get right, so if it doesn’t land, just move on. If you dwell on the stony silence, you risk making the audience feel like they must laugh at your jokes, especially if they are your subordinates. This kind of “emotional labor” makes employees feel mocked and exhausted.
Do: Keep a recovery line in your back pocket. If your wit provokes only crickets, it’s handy to have a go-to quip that gently acknowledges the flop and lets you move on quickly. Again, self-deprecation is your friend. One of my favorite gambits is to squint at the speech text and say something like, “That’s strange. In the script it says PAUSE FOR LAUGHTER.”
(4) Consider Context
Don’t: Joke about a crisis while still in said crisis. Context matters. Consider Cable & Wireless CEO John Pluthero, who amid plunging revenues and looming layoffs, penned a memo to staff that included the line, “Congratulations, we work for an underperforming business in a crappy industry.” Strangely enough, this did not cause the business to stop underperforming.
Do: Save humor for more lighthearted moments. Warren Buffett coined many of his most memorable quips in the context of Berkshire Hathaway’s annual meetings, where the tone is typically exuberant. For example, when talking about the tendency for reinsurers to behave recklessly, he said, “You don’t find out who’s been swimming naked until the tide goes out.”
Bonus “Do”: Test the Waters
If you are in any doubt, make like Hollywood and assemble a test audience. Find people you trust who represent your ideal audience, or a particular audience you’re worried about. Run your humorous lines past them. What do they think? Are you about to “pull a Ratner” or scale Buffett’s humorous heights?
Humor might seem scary at first. But if you ask me, it’s worth trying. To quote accidental comedian Yogi Berra, “When you come to a fork in the road, take it.”

