From Cringe to Connection: How Bad Jokes Build Better Teams

We’ve all been there.

You’re in a meeting that should have been an email, trying to lighten the mood, and you drop what you think is a perfectly timed joke. The ensuing awkward silence is more embarrassing than that time you weren’t on mute and flushed your toilet in the middle of the CEO’s business recap.

But that cringeworthy moment might actually be working in your favor, behind the scenes.

The Surprising Science Behind Workplace Awkwardness

Research from the University of Warwick found that happy employees are approximately 12% more productive than their unhappy counterparts (Oswald, Proto, & Sgroi, 2015). 

Okay, that’s nothing groundbreaking, we know. But it goes a little deeper than back-pats and complimentary coffee, when it comes to leadership in particular.

TL;DR: The key to unlocking success in the workplace isn’t being funny – it’s being human.

This is a magical formula as old as time.

Authenticity + Shared Connections = Successful Relationships

This equation creates what psychologists call “benign violation,” a safe space where people can laugh together without risk of hurt. Laughing with each other, not at each other.

Translation: Your dad jokes aren’t (just) annoying; they’re actually team-building exercises in disguise.

Why Your Puns Are Workplace Perfection

Let’s address the elephant in the room: Puns. They’re universally acknowledged as the lowest form of humor and almost as universally hated. 

But they’re also the most effective workplace ice-breakers. Why?

  1. They require zero cultural context.
  2. They’re completely harmless.
  3. They give everyone permission to groan collectively.

Research from Harvard Business Review confirms that laughter relieves stress and boredom, and catalyzes important interpersonal office skills like creativity, collaboration, and productivity (Beard, 2014). 

The reason for this is simple. When we’re not worried about saying the wrong thing, we’re more likely to actually say things. 

So the next time you contemplate throwing your stress ball at the actual source of your stress, stop to think. 

Because when your coworker says you’re Excel-ent at creating spreadsheets, they’re not (just) trying to be the office comedian. They’re creating a moment of shared experience that says, “For better or worse, we’re all in this together.”

The Art of Strategic Social Awkwardness

The most successful workplace humor isn’t about being the funniest person in the room. It’s about being the most relatable. Because if you’re not relatable, you’re replaceable.

So embrace the weird, the quirky, the awkward. Those are workplace superpowers, not liabilities.

Here’s how to take advantage of that in the every-day.

Start Small and Self-Deprecate

Begin with gentle self-mockery. Comment on your coffee addiction, your bad Zoom background, or that time you replied-all with a witty but entirely inappropriate comment that made it to the CFO. 

A 2018 study published in Personality and Individual Differences found that people with self-deprecating humor exhibit greater levels of emotional well-being and sociability (Torres-Marín et al., 2018).

In other words, if you don’t take yourself too seriously, then your employees actually will.

Use the “Callback” Method

When someone else makes a joke or shares a funny story, reference it later in casual conversation. This shows you were listening and creates an inside joke that strengthens your connection. 

For the money-minded: It’s essentially workplace humor compound interest, small investments that pay dividends over time.

Master the Art of Timing

The best workplace humor happens in transitional moments. Before Zoom meetings start, during coffee breaks, in the final moments of a touchbase. These are natural spaces where people are more receptive to levity.

Read the room, in other words. 

Shared Suffering, Shared Laughter

Nothing bonds coworkers quite like collectively surviving a system crash, a terrible new policy, or a meeting that could have been an email. These moments of shared frustration are perfect opportunities for humor that builds genuine connections.

The key: Punch up, not down. 

Make jokes about the situation, the system, or yourself. Never about individuals or groups, especially peers or direct reports. This creates an “us vs. the problem” mentality that strengthens team cohesion.

Research on humor in team interactions shows that teams who regularly engage in positive humor demonstrate better problem-solving abilities and more creative output (Lehmann-Willenbrock & Allen, 2014). 

People who master this skill are not just surviving their jobs – they’re actually enjoying them.

Quick Fixes: When Jokes Go Wrong

Even the most well-intentioned humor can misfire. 

We’re not talking about things that keep your HR Manager up at night, obviously; we’re talking jokes that should work just fine, but don’t. Clearly your sense of humor is on a whole other level.

When this happens (and it will!), resist the urge to explain further. Instead, acknowledge the flop and move on. You’ll earn more points with your people using self-deprecation than dying on a hill of bad wordplay.

This approach demonstrates emotional intelligence and shows that you can read the room – even if you occasionally misread it first

The Power of Leadership Self-Deprecation

For managers and team leaders, self-deprecating humor serves an especially important function. Research published in Frontiers in Psychology found that leaders who use humor against themselves are more likely to promote employee creativity while discouraging unethical behavior (Ahmad et al., 2021).

TL;DR: When leaders can laugh at themselves, it reduces the power distance between them and their team. 

That’s a win/win for everyone.

Creating a Culture of Constructive Humor

The goal isn’t to turn your workplace into a comedy club, but to create an environment where people feel safe to be authentically themselves – awkwardness and all. 

This means celebrating the colleague who always has a relevant GIF. Appreciating the person who names their houseplants. Recognizing that intern who signs off each email with a terrible pun.

Studies show that when people enjoy being around each other, they naturally collaborate more effectively (Humor That Works, 2020). 

The Bottom Line: Embrace the Cringe

Your workplace humor doesn’t necessarily need to be poised, polished, and professional 100% of the time. In fact, it’s often more effective when it’s a little rough around the edges. 

The goal is connection, not perfection.

So go ahead! Make that zinger about quarterly reports. Share your excitement about finding the perfect Notion template. Laugh at your own lame gags, even if no one else does. 

Your colleagues might roll their eyes, but they’ll also remember you as the person who makes work a little more human.

Because in a world of KPIs and performance metrics, sometimes the most professional thing you can do is be genuinely, awkwardly, authentically yourself

Go forth and make some mischief.

 

Building stronger workplace relationships through humor is just one way to create a more positive work environment. For more tips on bringing levity to professional settings, explore our collection of office-appropriate novelty gifts at Witty Yeti. May we suggest Computer Antifreeze?

 

References:

Ahmad, Z., Batool, A., Choi, J. G., & Lim, J. (2021). Humor of the leader: A source of creativity of employees through psychological empowerment or unethical behavior through perceived power? The role of self-deprecating behavior. Frontiers in Psychology, 12, 635300.

Beard, A. (2014). Leading with humor. Harvard Business Review, May 2014 issue.

Humor That Works. (2020). 30 benefits of humor at work. Retrieved from academic research compilation.

Lehmann-Willenbrock, N., & Allen, J. A. (2014). How fun are your meetings? Investigating the relationship between humor patterns in team interactions and team performance. Journal of Applied Psychology, 99(6), 1278-1287.

Mesmer-Magnus, J., Glew, D. J., & Viswesvaran, C. (2012). A meta-analysis of positive humor in the workplace. Journal of Managerial Psychology.

Oswald, A. J., Proto, E., & Sgroi, D. (2015). Happiness and productivity. Journal of Labor Economics, 33(4), 789-822.