You must always be careful not to have the possibility to offend anyone. Make sure that if the joke must poke fun at a target, the target is you. The shorter it is, the better. People who simply have no time or aren't in the mood won't mind that way, but the rest will smile or laugh. You, yourself might get tired of hearing yourself say it, but professional comedians do this all the time; they can memorize a spiel and tell it naturally and fluidly, from years of practice. The point is that you lightened the mood, made somebody smile, they subconsciously like you a little more, and you have also headed off a potential bad mood if the customer was already feeling a little stress.

Computers are a popular target. Stress from the inadequacies of dealing with computers are something any of us can identify with. And we all have computers at point-of-sale transactions, waiting for them to bring up an account, print out a receipt, or get an order loaded into the database. When working with computers behind a counter, I always took advantage of a hesitation on the machine's part. Again, this is just something fast, simple, and silly. Pick up the mouse and talk into it like a microphone, as if trying to wake the computer up, or move your hand by the side of the monitor as if you were turning an imaginary crank to make it run faster.

When it did what I wanted it to do, sometimes I'd pat it on top of the monitor and say "Good boy!" before turning back to the customer. This quick, silly gestures help to establish that I couldn't control everything, that slowness on my part was due to the machines and not my lack of trying. And it almost never failed that customers would launch into a remark or story about their frustrations in dealing with computers as well. It just helps to lighten the mood a little and everything goes more smoothly.

Sometimes, as in the phone menu example, it is also helpful to make a little light fun of your company's own bureaucracy. We all have to deal with filling out complicated forms: stamp this, staple that, file it somewhere, sign something, and so on. Be sure that you have your manager's approval for this one, and be sure you aren't putting down your own employer. The key here is to make a light poke at the system itself, so that your customer understands that it's the best way you have of dealing with something, but you realize it's not perfect. Paperwork, like phone menus and computers, is another minor hassle that we all have to put up with, and so this also helps to identify that you empathize with frustrations the customer might have with the inadequacies of your system.

Surprisingly, humor in customer service isn't actually so silly at all. It is serious business, costs nothing to implement, and in most cases can show an improvement on the bottom line. You just might laugh yourself right into a promotion!

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