The Art of Telling a Joke: Using Humor Wisely

Does Humor Belong In Business Writing?

by Michelle DiPoala

When I was asked to rewrite a job post for a high tech company, the CEO said he wanted to entice quality applicants by making the right first impression. The problem? He'd been informed that the tone of the Craigslist job posting made the fun workplace sound like a drag. (It did, we fixed it).

I know there's a ton of advice online sternly advising against using any humor at all, ever, in business writing. What, why not? In the right situation, with the right kind of humor, you can inject some life into those dreary job descriptions, make the employee handbook more readable, or you can break the ice with a pun in a welcome letter. You can certainly open with a joke in your quarterly presentation.

That being said, you do need to be careful with humor.

Joking is Serious Business 

The fact is, 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 experienced the awkward aftermath of seeing a joke go terribly wrong.

In a business setting, when a joke goes wrong, bad things can happen. All it takes is for one person to become embarrassed, hurt or offended by your joke, then your moment of merriment becomes a client complaint or a Human Resources grievance. How many smart alecks have ever mounted a convincing "But it was only a joke" defense that ends well?

The only thing worse than a cringeworthy joke made within earshot of an unappreciative listener in a workplace setting is one that you've put into a published document for serious people to read. In the spirit of demonstrating by example, here are three real-world cautionary tales that I've personally witnessed.

Make A Point Without Making An Enemy

It is ill-advised to risk alienating or insulting an entire segment of your audience for the sake of a snappy punchline. In any persuasion-based business writing, make your point gracefully. Don't make awkward wisecracks.

This cautionary tale happened in early 2017. I'd been asked by a Marketer to proofread her slide deck for a presentation that she would be giving at an industry 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. But to drive home her point, she added an anecdotal quip.

"Not everyone," she unfortunately wrote, "is a young, well-dressed white male."

I red-lined that particular bullet point with a note, "Seems a little aggressive." In this thought leader's case, her intent was good. 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 mocking every well-dressed, white male actually present at the conference just for being themselves. That's the opposite message. Had she left that in, the post-presentation networking event could have potentially been a disaster.

Balance "Personal" with "Professional" 

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

This cautionary tale happened in the days just preceding cloud-based software. The company where I worked used the services of an outside vendor for software kit manufacturing & distribution. The vendor made an unholy mess of things, including a deal-breaker of a misprint on the CD. 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 fully apologetic about the fiasco. Responding to my official written RCA request, she set up the big post-mortem meeting and sent a formal notice.

"We are so sorry," she unfortunately wrote, "we'll all get together and you can air your gripe."

This Account Manager's problem was twofold. Firstly, she used far too casual a tone in an official communication. Despite being friendly with me, she didn't consider that upper management, Finance and Legal also saw that note. Secondly, she may have been attempting to diffuse tension through word choice, but instead she created a B2B communication disaster. That's because the vendor's litany of mistakes on the line necessitated the entire production be re-done, at considerable expense and in a mad rush in order to make our launch date. The lighthearted tone, plus the connotation of "air your gripe" made a quite 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.

Slang: What Feels Right Can Go So Wrong 

This happened in the late 1990s at a large and growing tech company. It all started with a simple meeting agenda.  A Product Manager prefaced the agenda with a serious missive about the need to get all the dissenting stakeholders into one room 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 the "wad shooting" expression evolved from being a literal 1800s military term to a games metaphor (to be "all in" or to "go for it"), but by now it's become a completely different kind of expression found primarily in adult entertainment. That Product Manager, a kindly bespectacled gentleman who favored bow ties and plain chicken broth for lunch, most definitely intended no such meaning with his choice of slang. He was only attempting to reassure the team and promote the spirit of collaboration. But none of that matters to the conductors of the company gossip train. The actual agenda 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!)

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, and 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, but you could lose the respect of good people.
  • 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. 
  • Don't crack a joke that can become an embarrassment to you or to anyone else, internal or external to the company. 
  • 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.


Michelle DiPoala

I've been providing writing & content development for more than 20 years. I work with publicists & marketers, start-ups, corporations, educators, grad students, artists & musicians. Lately, I've been working mainly with publicists, marketers and start-ups, doing product descriptions, press releases, event & trade show materials, even Kickstarter campaigns. Aside from web content & business writing, I am also proficient in creative pop culture features and reviews on music, TV and movies. I blog about women's issues and politics. I believe that all writing is creative writing.













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