“Humor At Work Is A Balancing Act, Use It Carefully

Hi again, friends, family, fiends, foes, and all of you funky folks!

I’m looking into something today, that always gets people talking: humor at work. Now, I’m not just talking about the ol’ watercooler Dad-style joke or the chuckle you get from some dopey and unexpected pun. No, I’m talking about the fine art of balancing humor in a way that doesn’t turn you into the office clown or, worse, put you in hot water with your boss or the dreaded HR department. Humor is a powerful tool — it can boost morale, smooth over conflicts, and make those long days fly by a bit faster. But used carelessly, it can easily and quickly backfire, creating awkward moments or, worse, costing you credibility or the job.

Dean-ism: “In my experience, there are two kinds of people in this world, one who you want to have a drink with, and the other drives you to drink.”

So, how do you come up to that sweet spot, where humor is welcome and works in your favor rather than against you? Let’s look at what makes workplace humor effective, when to use it, and when to hold off.

1. Why Humor Matters in the Workplace

Humor has this almost magical ability to connect people, cut through tension, and make even the dullest meetings feel bearable. It can transform a dreary work environment into one that people actually enjoy coming to — and that’s saying something! As most of you know, I use humor daily on my show on Sky 7, and it is dynamite to help people get through a dreary or demanding day. Studies have shown that workplaces where humor is encouraged (within reason, of course) often have more engaged employees, better team cohesion, and a generally positive vibe.

But humor isn’t just about cracking dumb jokes. It’s about establishing a real and human connection. When you share a laugh with someone, you’re essentially saying, “Hey, we’re on the same team.” (common ground) Humor can help you break down hierarchical walls, too. A well-timed joke from a manager, for example, can make them seem more approachable and relatable.

The Key Takeaway: Humor makes the workplace a more pleasant place to be and can improve communication, making people feel comfortable and more willing to engage. Just make sure your humor is positive and inclusive — there’s no quicker way to lose friends than by alienating people with a poorly themed joke.

2. Different Types of Humor — Choose Wisely

Not all humor is created equal, and understanding the different types can help you to gauge what’s appropriate and what’s not. Here’s a quick rundown:

• Self-deprecating humor: This type of humor can be a great equalizer. It shows humility and helps others see you as approachable. But be careful — too much self-deprecating humor can make you seem insecure or lacking in confidence. I use this type a lot, and it does make me seem like people can relate to me easier.

Dean-ism example: “I am so old that I drove by a cemetery and two guys with shovels came out chasing me”

• Light sarcasm: When used sparingly, sarcasm can be funny and relatable, but it’s a very risky game. Sarcasm is easily misunderstood, especially in email or text form, where tone can be hard to decipher. Use it with people you know well, and keep it lighthearted.
• Observational humor: Observational humor — commenting on the everyday quirks of working life — is usually safe territory. Making a joke about how the coffee machine sounds like it’s planning a rebellion, or poking fun at the endless parade of pointless meetings, can lighten the mood without targeting anyone directly. (Careful about the subject, some companies hate to be criticized, even a little.)
• Wordplay or puns: Puns and wordplay are generally safe, and they don’t usually carry the risk of offending anyone. A good pun can be a great icebreaker or a way to ease tension. However, if you’re known as “the pun person,” remember: less is more. Puns are usually good for eliciting a “groan”…
• Situational humor: This is about reading the room and knowing when humor can help. If a tense meeting feels like it needs a breather, or a team is slogging through a difficult project, a well-placed joke can help break the tension. Just don’t force it — humor works best when it feels natural and unplanned.

3. Timing is Everything

Good comedians will say comedy is all about timing, and they’re not wrong. Good timing is the key to good humor to land well in the workplace. A quick joke in a stressful moment can help reset the energy, but throw that same joke in when people are focused or in a serious discussion, and it could fall flat.

Here’s a tip: Observe how others react before you go all-in with your humor. Try something light and see if it’s well received. People’s body language, facial expressions, and overall vibe can give you clues about whether they’re up for a laugh or not. (If not, don’t try it, I have learned from vast, hard earned experience.)

Pro Tip: Avoid jokes in email or written form if possible. Humor often relies on tone, and without vocal inflections or body language, jokes can easily be misinterpreted.

4. Keep it Inclusive

In a diverse workplace, humor that’s funny to one person might be offensive or confusing to someone else. As much as we all love a good laugh, remember that everyone has different boundaries, backgrounds, and sensitivities. Stay clear of jokes that poke fun at someone’s personal traits, beliefs, or background. Keep it safe, keep it friendly, and remember: if there’s any doubt about whether a joke might offend, it’s best to leave it out.

One of the safest bets? Self-deprecating humor. It shows that you’re comfortable enough to laugh at yourself and doesn’t target anyone else. Just keep it in check — too much self-deprecating humor, and people may start to question your self-confidence.

Example: Instead of making a joke at a colleague’s expense, say something like, “Well, I guess I’m doing my best impersonation of a Monday morning zombie today!” It’s light, doesn’t offend anyone, and is something most everyone can relate to.

5. Know When to Draw the Line

Sometimes, the best humor is knowing when not to be humorous. There are situations where humor can actually be badly counterproductive — during performance reviews, when discussing serious issues like ethics or HR matters, or when giving some constructive feedback. In these cases, humor can kill the message or make it seem like you’re not taking the issue seriously enough.

Similarly, if you find yourself in a situation where people are clearly stressed or frustrated, humor might not be welcome. The key is to use humor to build bridges, not to blow them up, like the “Bridge On The River Kwai”.

A Final Tip: If you accidentally make a joke that doesn’t land or, worse, offends someone, own up to it right away. A simple “Oops, that didn’t come out right — I’m so sorry!” can go a long way in repairing the moment.

6. Recognize When Humor Can Help — and When It’s Essential

While it’s clear that humor isn’t always appropriate, there are times when it’s not just helpful — it’s essential. Humor can be a fantastic tool for keeping morale high during tough times, such as when deadlines are tight, or the workload feels overwhelming. A little light-hearted banter in these situations can remind everyone that, at the end of the day, we’re all human, and we’re in it together.

When you can create a shared laugh during tough times, it’s a reminder that no one’s alone in the struggle. Humor builds resilience, and in many ways, it’s one of the most underrated tools for fostering team spirit and a sense of camaraderie.

Example: Say your team is struggling with a technology issue that’s out of their hands. A comment like, “Well, I guess we’re all becoming masters of patience today!” can give everyone a chuckle and lighten the mood just enough to keep spirits up.

Dean-ism: “Technology is our friend, right??” (drip it with sarcasm)

7. Let Your Authenticity Shine

If you’re naturally funny, let that shine — but keep it real. Forced humor can be just as icky as saying nothing at all. Your colleagues will appreciate humor that feels genuine and in line with who you are. Trying to adopt a comedic persona that doesn’t fit you will come across as forced and disingenuous.

The Bottom Line: Humor is a fantastic tool when it’s authentic, inclusive, and used wisely. Don’t be afraid to lighten up a little, but make sure you’re reading the room, respecting boundaries, and letting people laugh with you, not at anyone. Workplace humor is, indeed, a balancing act. Used well, it can transform the daily grind, boost morale, and build connections. But like all good things, moderation is key. Keep it light, keep it respectful, and let humor work for you — not against you.

Dean-ism: “At my fourth trip to the buffet dessert counter, my friend, Mike, said aren’t you even a little bit embarrassed? I said no, I keep telling them it is for you!”

Dean Benson, “The Dean Of Rock & Roll” SKY7music.com middays on the “Only Classic Rock Channel”. Also see more of my writing at: https://stan.store/DeanBensonRocks .