Updated: Aug 23, 2019
I remember one of the first business presentations I attended here in Japan, now more than 25 years ago. The presenter, an American working in Tokyo, began by saying that most Japanese speakers open with an apology, and that most Western speakers open with a joke. So, he said, "I'll start by saying, 'I'm sorry I don't have a good joke to tell.'"
Many of us chuckled. A few months later, another speaker at a similar business event tried the same introduction and he received only groans from the audience. Here's the truth: Unless you're a professional comic, you're probably not funny enough to tell a joke at the start of your presentation. Oh, you can tell it, but you won't get the result you want. And what is that result, anyway?
Did you want the audience to think you're funny? Maybe. But they didn't come to your talk for the laughs, right? The reason (I hope) you're even thinking of telling a joke at the start of your presentation is to generate a connection with your audience. And that's great. Westerners, according to the excellent book "Polite Fictions," by Nancy Sakamoto, live under the fiction that "You and I are equal." And what says "equal" more accurately or quickly than laughing at the same joke? So your heart's in the right place.
Japanese operate with different "polite fictions," and, as is often the case in the Japanese language, the best thing to say is often "nothing at all." Certainly you wouldn't want to make a lot of noise, laughing out loud, at a business presentation. So telling a joke at the start of a presentation to a Japanese audience will likely generate nothing but silence.
But here's the hard truth: You are probably not that funny anyway. If you're the boss, you're accustomed to people laughing at your jokes. The real news is this: They're laughing because you're the boss, not because what you said is really funny.
As an aside, a story I heard and often retell is one that may or may not be true, it makes the above point. It seems that former US President Jimmy Carter once spoke to the Japanese Diet (Congress), and he was using an interpreter. He began his talk with a joke, and was pleased at the response of the audience, since he wasn't sure if his humor would carry across the Pacific. After the speech, he complimented his interpreter, who said, "Oh, I didn't really translate your speech. I just told them that the President of the United States just told a joke, so please laugh."
Ninety percent of the time that I tell that story to an audience, I get quite a bit of laughter. But note that it's not a joke, and though I told you that you're not funny, I admit that I'm not funny either. At least not "professional" funny. Nobody has paid me to make them laugh. And unless they've paid you to make them laugh, my advice is, stay away from jokes.
You can still share your sense of humor, you can be self-deprecating, you can even sometimes get away with putting up a comedic slide or funny short video clip in your presentation, but remember your objective. Or better, remember your audience's objective. Did they come to see you in order to hear jokes? To be read to? To be baffled by tough-to-read slides? Not likely. Remember their objective so that you can hit yours.