• Michael Cundall Jr.

Lead with a Joke


One of the common bits of wisdom for anyone taking a new position or heading a new team, is not to lead with a joke. The audience is probably too full of questions, apprehension, and plain old wonder to get a joke. The words you’ll say will be scrutinized, your body language picked apart, and any ideas you may proffer, put under a skeptical lens.

Imagine being the CEO following Bill Gates, or inheriting a troubling situation like Uber a few years ago amid the fury of the frat boy culture. Jokes in these situations may not be the best strategy. But perhaps they can be. Actually, they are more than possibly good, it can be just what's needed to get moving and get moving quickly.


Like many of our social rules, the rule to not lead with a joke isn’t hard and fast. Sometimes humor might be the only weapon one has in her arsenal to dispel, or put on hold all the apprehension and nervousness.


If you’re being introduced to a new group because of some difficult circumstance, why try and fight it? Note the elephant in the room, maybe play on it with some word-play, and move on. If the joke is light enough, you’ve acknowledged the issue, and very quickly moved past it. But be careful not to use the joke to brush it off. Many politicians can be seen to do this. Looking at you Joe Biden. Since humor causes the mind to focus on a different set of concepts for a moment causing a moment of good feeling, this will do more to dispel the negative emotions than any amount of hand-holding, or careful wordsmithing might. The joke immediately acknowledges the issue and given the rapid switch to resolving the humor, the mind doesn’t linger on it. The mind moves to the enjoyable trick the humor brought to light. And with that in play, the subsequently more difficult task of starting with the new group is all the easier.


It’s important to see how the rapidity of humor works to the speaker’s advantage. The listener is invited to think in a certain way. But the humor plays off of that and makes the listener focus momentarily on something else. This focus engages us to solve the puzzle. How does the new bit of information fit into the situation? What’s going on? Did he really just tell a joke? Once the mind resolves the issue there is a reward, the humorous mirth. This feeling will counteract all negative emotions if only for a bit. But that bit is more than enough. If the joke lands, then the remaining part of the meeting can proceed less encumbered.


So that’s the cognitive part of the process. The hardest part, by far, is getting the joke to land. How do you know if the situation is going to lend itself to a joke? Maybe the air is just too heavy? There is no easy answer. There are a couple of important things to note. Humor needs to start from a place that’s authentic. If your audience thinks you’re not fully behind the joke, then you’re done. You have to own it. A half-hearted joke can land you full-throated criticism. The joke also needs to be easy enough to process, but not so difficult that it causes deep thought. “Deep” jokes don’t work here.


A good leader can also sense what the room needs, what the audience wants to hear. If you’ve been invited to take over a situation, then you’ve worked with enough people to be able to read the room—that’s assumed. What’s that read telling you? Are you holding back cause you’re nervous? They are too, or maybe the audience is jaded. In either case, the well-placed joke can work to your advantage. Showing a sense of humor amidst crisis makes you seem confident, provided you're still actually leading and not ducking behind the joke. People like working for and with someone like that. If that’s what people want, then by all means give it to them.


Try to lead with a joke, both when you first meet and later. It can’t be all the time, lest the humor lose its meaning. But it most certainly can make for better work and you'l be a better leader for it

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