Those who think humor and business don’t mix should check out Jeanne Dinnini’s recent post Show ‘Em Who’s Boss, which makes a disagreeable topic digestible by adding the spice of humor.

Her topic is rather personal. Jeanne casts the spotlight on no fewer than 30 character flaws of ineffective bosses. Here’s one of my “favorites”–

Be hyper-critical. Never fail to point out the faults of others at every possible opportunity–preferably in public and the more people around, the better. This not only keeps people on their toes, but also shows that you have real insight into the inner workings of the human psyche.

Now, if Jeanne had made this point with a straight face, chances are that any boss reading it would respond by lashing out and/or never reading Writer’s Notes again.

As it is, the gentle smile behind the words softens up readers just enough to let them absorb the message. I think in this case, humor turns what could easily have been a pointless rant into a teaching opportunity.

In sales, a well-timed joke can diffuse a tense confrontation with a customer. But it’s a fine line. Where have you seen humor help in a business situation? Where have you seen humor backfire?