The Art of Telling a Joke: Using Humor Wisely

Recently I was asked to punch up a job post for a high tech company. The CEO said he was trying to entice quality applicants, but he'd been informed that the tone of his job post made a fun workplace sound like a total drag. It did. We fixed it, and we did it with humor.

Does Humor Belong In Business Writing?

I know there's a ton of advice online sternly advising against using any humor at all, ever, in business writing, whether it's a job posting or a client email. I say, why not use humor? When done right, you can add some spark to those dreary-sounding job descriptions, make an employee handbook more enjoyable to read, or you can break the ice with a pun in a client welcome letter. You can certainly open with a joke in your quarterly presentation, in fact, there's a tradition about that...but make no mistake: you do need to be careful with humor in business writing.

Joking is Serious Business

Few things in life are as fundamentally subjective as our own self-perceived sense of humor.

In a social setting, when jokes go wrong it's primarily for one of two reasons. Either you're simply not that funny and no one gets you, or you are really quite funny, but you manage to offend someone. We have all witnessed, at some point, that incredibly awkward moment after a joke goes horribly wrong. It's why the word "cringeworthy" was coined.

In a business setting, when a joke goes horribly wrong, worse things happen. All it takes is for one person to become embarrassed, hurt or offended by your little joke, then your brief moment of merriment becomes a real issue. A client complaining to your boss or a coworker filing a Human Resources grievance is no laughing matter. Ask yourself this question: how many smart alecks have ever mounted a convincing "But it was only a joke" defense that ends well for them?

The only thing worse than a cringeworthy joke made within earshot of an unappreciative listener in a workplace is one that you've written down in a published document for serious people to read. Here are three real-world cautionary tales about being careful with  humor in the business world.
Make A Point Without Making An Enemy

A Marketer asked me to proofread her slide deck for a presentation at a conference. Her topic: democratizing web content so it appeals to a wider audience. In one of her bullet points, she suggested using images that include a variety of different people as a way to engage a wider group. Thoughtful advice, very good. To drive home her point, she added a little quip. "Not everyone," she unfortunately wrote, "is a young, well-dressed white male." I red-lined that particular bullet point with a note, mildly worded, "Seems a little aggressive."

Her intent was noble. She sought to challenge a group of people to do better by communicating online in a friendly, inclusionary manner. So focused on making her point, she went too far in the other direction, inadvertently alienating every well-dressed, white male actually present at the conference. Not good. Had she left that in, the post-presentation networking event could have potentially been a disaster.

Balance "Personal" and "Professional"

"Personalization" is currently leading the way forward in B2C and B2B communication, aided by a massive sub-category of marketing tools designed to help nurture and maintain strong client/vendor relationships. Such emphasis on one-to-one relationships may blur the lines, maybe you aren't sure when it's okay to crack jokes in your customer communication. Rule of thumb – and fingers and toes –  be professional at all times, please.

This cautionary tale happened in the mid-1990s, before cloud-based software releases. No downloads. That means physical kits with software on CD, hard copy manuals, and pick/pack/ship distribution. For one software release, our vendor made an unholy mess of things, including a misprint on the CD. They'd actually gotten the product name wrong, and for some reason, had printed the entire run, skipping the vital step of sending one to me first so I could check everything and sign off on it. That was...really bad. I wrote up a formal request for root cause analysis (RCA).

I had a good relationship with the vendor Account Manager. Over the phone she was sincerely apologetic about the fiasco. Responding to my official written RCA request, she set up the big post-mortem meeting and sent around a formal notice with the date and time. "We are so sorry," she unfortunately wrote, "we'll all get together so you guys can air your gripe."

This Account Manager's problem was twofold. Firstly, she used far too casual a tone in an official communication with "you guys." She didn't consider that upper management, Finance and Legal would see that notice. Secondly, while she may have been attempting to diffuse tension through word choice, instead she created a B2B communication disaster. The lighthearted tone and connotation of "air your gripe" made my company's very serious incident report sound like a mere petty annoyance. The attempt to lighten the tension only served to increase it, and destroy confidence in that vendor. Unacceptable.

Slang: What Feels Right Can Go So Wrong

This tale started with a simple meeting agenda, sent by email. A Product Manager prefaced his email with a serious missive about the need to have all the stakeholders meet urgently for a deep dive decision-making session. "You will all," he unfortunately wrote, "get a chance to shoot your wad."

Oh boy.

The Product Manager's gaffe was a problem of evolved language. It may have taken several hundred years but that "wad shooting" expression evolved from being a literal 1800s military term to a games metaphor ("shoot your wad" was slang for "go for it"), but by now it's become a completely different kind of slang, one found primarily in adult entertainment. That kindly bespectacled older gentleman, who favored neat little bow ties and plain chicken broth for lunch, most definitely intended no such lewd meaning. He was only attempting to reassure the team, and promote a spirit of productivity through in-person collaboration. But none of that matters to the conductors of the company gossip train. That actual email only went to about ten people, but by the end of the day, the entire company knew about it. Awkward.

Use Humor Wisely (If In Doubt, Leave It Out!)

Yes, you can definitely use light humor in business writing. A harmless pun, a dash of whimsy here and there can add sparkle and keep readers interested – but be mindful of your entire readership. That is to say, if you find yourself saying, "Pat in Business Development is going to crack up at this," have you considered the opinion of everyone else who is not your good friend Pat? You won't have the same exact relationship with every reader. What's an inside joke to you and Pat may trigger an unexpected reaction in others. You might not lose your job. You might not lose a customer. You might, though, lose the respect of good people. Don't crack a joke that can become an embarrassment to you or to anyone else, internal or external to the company.

  •     Make sure you know what your words mean, considering both definition and connotation.
  •     Be on the lookout for inappropriate slang in your day-to-day business writing.
  •     Seek to avoid any joking that can be construed as an -ist, like racist, sexist, ageist and so forth.
  •     Have someone objective read through your items before you send, print or publish.
  •     If in doubt, leave it out! The risk of causing chaos is not worth it.∎