If you really need to know how funny you are, you could test your hilarity with someone who doesn’t depend on you for a paycheck. But that might not turn out the way you hoped. This is one of the many, many instances in which ignorance is your friend. As things stand, your subordinates laugh like inebriated chimps at everything they hope is meant as a joke. That artificial approval makes you feel like a superstar, and it makes your subordinates happy, because fake laughing is easier than working. It’s a perfect system. I wouldn’t peel back the layers on that onion.

I would like to showcase my sense of humor at the office. What are the best opportunities for doing so? I’m guessing downsizing announcements are not ideal.

There’s no better time for humor than when you’re criticizing a subordinate. Humor can lighten the mood in what might otherwise be a tense situation. When you criticize subordinates in a boring and normal way, you end up with crying, shouting, and sometimes violence. But if you whimsically compare your ineffective subordinate to a nutless squirrel with a learning problem, the situation quickly turns
to laughs, hugging, and-;with a little luck-;inappropriate touching.

Is it better to be funny about stuff that’s specific to the workplace, or can I be more broadly humorous? I have material I worked up for Toastmasters last year that most people here haven’t heard.

People prefer humor they can relate to. For example, if you tell a funny story about the time your personal chef fell off your yacht and you let him drown because you didn’t feel like going back, your employees will find that relatable. At least from the chef’s point of view.

I worry about making a joke that might offend somebody. How can I be both hysterical and politically correct?

It’s perfectly acceptable to tell offensive jokes at work, as long as you add to the end of each one, “Ha ha! It’s OK, because I dated one in college,” or “Ha ha! It’s OK, because I tried it once at summer camp.” That covers most bases.

I am, by nature, a strategic thinker. How can I think strategically about deploying my humor?

That is an excellent question, because humor without strategy is like a pair of mittens with no user manual. It’s all trial and error and tears. That’s how accidents happen.

Humor can’t be randomly sprayed into the universe with no thought of an endgame. Humor requires a strategy that connects your wittiness with your long-term goals. For example, one long-term goal might involve trying to appear somewhat human, for reasons that are not immediately obvious. Or maybe you like to use humor to belittle subordinates so you can enjoy the warm glow of your own arrogance. There are plenty of good reasons for a CEO to be funny. You just need to pick one.

How can I be sure my employees are laughing with me, not at me?

You don’t need to live in doubt. The best strategy is to laugh at them first. As soon as you deliver your punch line, point to the weakest nearby person and yell “LOSER!” then laugh as if there are kittens in your underpants. I don’t know exactly what your employees will be doing at that point, but it probably won’t involve laughing.