One of the hardest chapters in The Fun Habit to write was “Bring Your Fun Habit to Work.” I could have taken the easy road and created a list of things to try—a menu of trite tactics. “Ideas” that pose the reader little risk, but ultimately would likely never be memorable by anyone as real fun. Instead, I exposed fun’s dirty little secret — that true fun at work is sometimes a challenge. Of course, it is. One of the best things about fun is that it’s uniquely ours to define.
Funny is no different. We all have different preferences when it comes to humor, so what seems funny to one risks being horrendous to another. Don’t get me wrong, in the right context, sometimes bringing a bit of funny to the workplace is a great idea. If the workgroup participating in whatever humor has been created also has a degree of shared connectedness and consideration for one another, enjoying something like a good joke is a great way to strengthen bonds. The problem is, unfortunately, that some believe humor is a universal workplace booster—and that’s untrue.
When Fun Becomes Fatigue
Unfortunately, leaders are some of the most likely to think their brand of humor will foster camaraderie. Outwardly, employees will signal amusement as a form of surface acting. Few want to make the boss look bad. Inwardly, though, all too often employees experience their manager’s attempt at humor as awkward, cringeworthy, or—worse—as stressful.
I recently had the good fortune to learn more about this phenomenon from Dr. Randall Peterson, a fellow organizational psychologist who has researched the effects of joking at work. His findings reveal a troubling reality: Humor from higher-ups carries a significant risk of leading others to emotional exhaustion.
Why? Because when a boss tells a joke, it’s rarely just a joke—it’s an implicit social cue. Subordinates often feel pressured to laugh, not because they find the remark funny, but because not laughing feels like a risk. There’s an unspoken expectation: laughing along signals agreement, enthusiasm, and team spirit, while silence can be misread as defiance or disengagement.
The problem: Over time, this dynamic can erode workplace well-being. Instead of being a lighthearted morale booster, forced humor becomes another obligation that drains energy rather than replenishes it. Like all forced fun, it is particularly harmful to employees who feel they don’t have a choice. Research shows that for workplace humor to have a positive effect, it must be inclusive, voluntary, and contextually appropriate. When those conditions aren’t met, what’s intended to be uplifting can quickly become just another form of work fatigue.
The Fine Line Between Connection and Coercion
The key is optionality. Humor works best when it emerges naturally rather than being imposed. If you’re a leader, your employees should feel free to engage—or not—without consequence. The moment laughter becomes expected rather than spontaneous, it stops being fun and starts being performative.
Dr. Peterson’s research highlights a crucial distinction: Leaders who self-monitor their humor build stronger workplace rapport than those who assume their jokes always land. In other words, the best leaders aren’t the ones constantly cracking jokes—they’re the ones who can read the room.
When humor is used well, it relieves tension. A well-timed joke can defuse stress, lighten the mood, and foster connection. But humor in poor taste—or humor that feels obligatory—does the opposite: It creates tension and distance. Employees shouldn’t have to wonder, “Do I need to laugh at this to stay in good standing?” True workplace camaraderie isn’t built on forced reactions; it’s built on trust, agency, and authenticity.
A Day Without a Laugh is a Day Wasted
Forced fun is never fun, and expecting to get a laugh from your team all the time certainly falls into that camp. But, of course, a workplace devoid of laughter is awful, as well. As the great John Cleese once said, “Laughter is a force for democracy.” Humor is an important part of the human experience, and for many of us, a majority (when measured by time) of our human experience happens at work.
So, how can leaders strike the right balance? When I posed this question to Dr. Peterson, his advice was refreshingly simple: Just tell a few jokes you feel are appropriate, actually good, and relevant to the moment. Good leaders treat humor as a natural extension of connection.
Not sure you’re funny? Even if you are not an inherently funny person, when you attempt a few well-timed jokes, chances are your employees will still likely value the attempt and intent. Just don’t let their laughter fool you into thinking you’re as funny as Steve Carell—because chances are, your humor is closer to the awkwardness of Michael Scott (and if you don’t get that reference, there’s a good chance you need to work on your material anyway).
