Most folks would agree that there is a fine line between humor and offense. As that gray line is relative, and could be anybody’s guess. What one person may think is hilarious, another group may think is totally off-color and offensive. How can you tell the difference?

Before humor is introduced to any audience, regardless of its size, demographics and culture, you must first research and learn about the people you’re working around. The worst thing that you can do in an office setting is tell a joke or a funny story that ends up alienating more folks than you made laugh. Humor is delicate, very delicate and must be handled as such. Here are some tips and strategies that I have used in my 20 years experience of helping offices to “lighten up”:

Me Strong!

Know who the Type A, Alpha Male/Female in the group is. Identify that strong personality and cater to them like nobody’s business! Since this is the person who generally makes final decisions, be sure to stay on their “list” to keep him/her happy. Find out what they like/dislike and their brand of humor style. Trust me – they have one. You’ve just got to find where it is. This one naturally leads to…

Take Your Queues from the Head Honchos

Basically, if the boss doesn’t laugh, neither should you. Sounds stifling? Probably is, but you want a job next week, don’t you? Yes, I know bosses can sometimes be drier than day old toast, but what are you going to do? As hard as it may be, until you find that “happy place” that has your boss hostage, you simply must go with the flow my friends. After a while, it will become easier as you learn his/her humor style, behavior and funny threshold. Just hang in there.


Never, ever, ever, ever under any circumstances tell off-color jokes in a large office gathering. There are times and places for certain jokes and stories, and the office setting may not be appropriate for them all. You can offend, alienate and downright make some folks mad. Save those jokes for the weekend bar-be-que when the boss is not around, k?

There are a ton of other applied methods that I’ve laid out in my workshops and in my books about workplace humor. As a humorist, I show corporate environments how to lighten things up in the workplace short of locking the boss up in the closet. OK, I’m kidding. Kind of. But what is so unique and fun is finding those strategies that work wonders for YOUR office since everyone is so different.

What workplace challenges does your office face in relation to humor? Do you have one of those “quirky” bosses who finds nothing funny or humorous? How do you work around it?

Brad Montgomery
Motivational Keynote Speaker, Humor in the Workplace Consultant, Humorist

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