Clowning and Closing: The 3 Ws (and 1 Big H) of Using Humour in Your Business Communication

Can I use humour in my professional communications? Absolutely… but it can get unfunny fast if you don’t do it right. Proposify technical writer and resident wit Allan Duquette is here to educate AND entertain you with his best practices and examples for adding some comedy to your sales and other business docs for fun and profit.

a recipe for humour in business being cooked

7 min. read

Have you ever found yourself halfway through giving a presentation and realized that you’d lost everyone? Have you sat in a presentation all the way through and found yourself feeling good? Odds are someone threw a joke in the mix.

Throwing humour in your presentation is a great way to warm your audience up and make them more receptive to the points you need to make. If that’s the case, why are business documents so dry?

Part of the reason is simple: You have to watch your language with certain writing to prevent confusion. One tech writer was told by his boss, “That’s a cute joke. Do you want to explain the punchline at a tribunal?”

But here’s the thing: unless you’re in a business where people’s lives hang in the balance, adding a bit of humour can help, just like making an ice breaker joke.

In this post, I’m going to show you how I use humour in my technical writing to make it stronger and give you my best tips and advice on why, when, where, and how you can add a bit of fun to your sales and other professional documents.

Why should you use humour in your business communications?

Other than “It’s fun” and “People seem to like it” and “My mom thinks I’m funny”, there are two key reasons that humour and business can work well together:

1. It keeps people reading

Release notes at Proposify used to be internal-only and incredibly dry. Think ‘saltine in the Sahara’ dry. During these dark, humourless days we’d be lucky to see five readers keep abreast of the changes in the app.

Out of boredom and frustration, I began writing silly punchlines at the end of the notes. That number jumped up to 60 readers in a week. What’s more, they came back the following week, and the one after that, and the one after that.

This works for your sales material, too. Make your prospect smile in your introduction paragraph and they’ll wonder if you have more. One weapons-grade dad joke can boost engagement just as much as a graphic design boost. Humour gets people to pay attention, helps them understand and remember by making what we’re saying relevant and relatable, and, hey, it improves our likeability.

2. It shows you’re human

B2B doesn’t mean “faceless company to faceless company”. You’re both humans with human worries, struggles, and stresses. Observational humour is all about bridging that gap and finding the relatable struggles we all face.

For example, we’ve all related to the struggle with airline food and how rigid the chairs are. Not only are you self-aware, but you’re also showing that you share that pain.

On the digital side, I recall using project management software that had a hidden “anxiety mode” on their marketing page. If you selected “tell me more” six times, the friendly, professional copy revealed their all-too-common anxieties: problems with their dev cycle, product-market fit, and technical debt. This little ‘Easter egg’ had me laughing because they’d captured my experience and slapped it on a page with colourful stock photos.

an example of a template service notice

When should you use humour in business communications?

Naturally, it’s not appropriate to add a joke to every situation. While your late Aunt Gladys would love you to roast her at her funeral, your dad may not find it as cute.

Timing is the riskiest part of comedy so here are three general guidelines about when to use it in professional communications.

Great time to use humour: Breaking up dry content.

Sometimes you need to get important ideas across. Many times, however, those ideas will put your audience to sleep. Peppering a quick joke between every few points will keep your audience’s eyes on what you need them to see.

Less great time to use humour: When you need to be clear.

No one’s keeping Torto the Acquisitions and Mergers Clown on retainer. If your content requires a lot of focus to get through, adding a joke could be distracting.

However, like release notes, there are certain areas where you can fit one in and sometimes a silly analogy can even help explain a concept. (Check out my examples below for more on this.)

Terrible time to use humour: When you screwed up.

Making light of your mistakes is a good way to garner forgiveness, but there’s a limit. If you lose your customers’ time, data, or (worse) money: don’t joke. Joking after accidentally breaking a plate shows you’re easygoing; joking after breaking a TV gets you banned from future Super Bowl parties.

an example of a sales pipeline service notice

How to add humour to your business communication the right way

The biggest concern over humour is the fact that it’s a lot of work for a lot of risk. You can agonize over punching up a joke only to have it fall flat or be misinterpreted. Or you could turn your readers off entirely.

Some things to keep in mind to make sure a bit of fun in a business document doesn’t become a distraction (or worse):

Keep it as a treat

Jokes on every line are exhausting, both to write and read. Treat humour like a small reward for getting through something dry.

“Thank you for reading the technical specifications for our cheese vats. I hope this keeps you from getting ‘a queso the Mondays’. Get it? A queso th—you know what, I’ll just see myself out.”

Make it content-adjacent, not THE content

The popular comedy TV show The Good Place often had to have serious dialogue to keep the plot going. So since it was a comedy show written by comedy writers, they added silly business names in the background. This is how the main characters would end up addressing personal faults next to a food stand labelled “A Knish From A Rose”.

Add a funny Easter egg in a testimonial or an image when you need clear copy. Bonus: if your prospect mentions it, you know they’re paying attention.

The joke’s always on you

Making fun of yourself shows you’re self-aware. Making fun of others, as an organization, shows you’re a troll.

There are plenty of companies who position themselves with that image and they do just fine. One day, though, you may find yourself needing a different market position. When that day comes, distancing yourself from that previous edginess will be difficult. Keep your options open by keeping the joke on you.

Proposify's State of Proposals 2022 eBook cover and introductory pages

Millions of proposals. Thousands of survey responses. Ten actionable takeaways.

The analysis and insight you need to dominate your deals in 2022 is right here.

4 examples of using humour in technical documents

Look, we all know the best way to kill a joke is to explain the punchline. But here are a few examples of jokes from our own release notes to help you strike your readers’ funny bones just right:

Example 1:

an example of onboarding service notice

How is proposal software like a Swedish home-furnishings store? It’s not and that’s what makes this analogy both funny and familiar, which is great for explaining a process change.

Example 2:

an example of editors service notes

There’s always content you want to prioritize in your docs. Adding absurdity helps lighten the tone on the smaller details when you want to keep the reader moving to the bigger, more important stuff.

Example 3:

prospects outreach email reminders advice

Want to make your writing more relatable? Point out an unspoken truth—like that horrible feeling when you think you just got caught sending an auto-reply.

Example 4:

an example of an editor issue notice

When all else fails, there’s always slapstick.

Who is humour for? Humans

Sales is a serious business. Just like life, though, you can’t take it all too seriously.

Lightening the mood gives your audience a glimpse into your personality, allowing you to make a connection that can’t be expressed in an itemized list. Sure, there’s always a risk, but the rewards to your brand and your own success can make it worth adding a clown nose to your business suit every once in a while. Give it a shot!

Clowning and Closing: The 3 Ws (and 1 Big H) of Using Humour in Your Business Communication

    Proposify's mascot, P, in a blue suit. Coffee is for closers

    Ready to start winning from home?

    We’d love to show you more about how Proposify can help improve your proposals and streamline your sales process.