How Humor Strengthens Trust, Collaboration, and Innovation at Work 

What if your next big innovation didn’t start with a brainstorm—but with a belly laugh?

The idea for this session began after I watched a LinkedIn Live hosted by Sam Ervin and Madison Fisher Romashko on the topic of retrospectives. Sam held up a book on humor in the workplace during their talk, and I couldn’t help but think—yes, more humor in the workplace. Inspired by his authenticity, insight, and spontaneous wit, I reached out to ask if he’d be open to speaking at Agile Boulder MeetUp. Thankfully, he said yes—and what followed was one of the most engaging, creative, and psychologically safe sessions I’ve ever hosted.

At the Agile Boulder Meetup, Sam Ervin invited us to explore humor not as a distraction from work, but as a tool for making work better. Drawing from personal stories, agile team dynamics, and light improv, Sam made a compelling case that humor isn’t just a nice-to-have. Humor is a key ingredient for psychological safety—and a predictor of trust, resilience, and creative thinking at work.

Humor helps us with “balancing the gravity with the levity.” —Sam Ervin

It reminds us we’re human—and that we’re in it together.

Research backs him up. According to studies by Gallup, teams with high employee engagement (which includes having fun together) are 21% more profitable. McKinsey reports that humor and play are core characteristics of resilient, high-performing teams. But even without a statistic, we all intuitively know: laughter breaks down walls. It signals safety. And when done well, it changes the emotional climate of a room instantly.

Below are the five essential elements Sam introduced—and why each one matters deeply to psychological safety.

1. Know Your Audience

Humor without context is like a joke without a punchline—awkward at best, damaging at worst.

Psychological safety begins with empathy, and knowing your audience is an act of respect. In one story, Sam described delivering a monologue using dating app jokes to one agile team—and getting roaring laughter. When he recycled the same bit at a different conference, it bombed. The difference? The first group shared his generational context. The second didn’t.

This principle is about more than comedy. It’s about situational awareness. Humor that builds connection is rooted in shared language and experience. That kind of humor signals: "I see you. I get you. I belong here, and so do you."

Psych Safety Link: When people feel understood, they speak up more freely. Shared jokes can be the first proof that a group "gets each other".

2. Know Your Voice

Humor isn’t one-size-fits-all. Some people are storytellers. Others are observational quippers. Some thrive on absurdity. The point isn’t to be someone you’re not—it’s to find the voice that feels most natural to you.

In psychologically safe environments, people are encouraged to bring their full selves to work. That includes their humor. Sam encouraged us to "mine the ridiculous" and explore what makes us laugh. Because when you use humor in a way that aligns with your personality, it comes across as confident, not performative.

Real Talk: You don’t have to be a stand-up comic. You just have to be real. And when people see you being real, they’re more likely to be real too.

Psych Safety Link: Authenticity invites authenticity. Humor is one way to model vulnerability—and make it safe for others to follow.

3. Use the Element of Surprise

Humor often relies on contrast: the unexpected twist, the ironic turn, the shocking juxtaposition. That surprise opens the brain to curiosity.

Sam shared a story about a tense meeting with senior leaders. A participant compared the team’s outdated processes to AOL sending compact discs in the mail. Sam saw an opportunity. He added a joke to the virtual whiteboard: "Best idea yet: Annual Compact Disc Mailing!" That single sentence cracked the tension and broke open laughter.

Psych Safety Link: Tension is the enemy of creativity. When surprise is used gently, it signals, "We don’t have to be stuck. Let’s get playful."

Surprise isn’t always funny. But when it is—and it’s kind—it can interrupt groupthink, relax the room, and open up new possibilities.

4. Mine for Truth

The best jokes don’t hide reality. They reveal it.

Sam taught us a key comedic principle: “It’s funny because it’s true.” He used an exercise comparing imposter syndrome to real-life situations like karaoke, skydiving, or brushing your teeth upside down. These metaphors helped participants reframe discomfort, while also naming the emotional experience underneath.

Humor is a form of storytelling. It lets people express what might otherwise be too vulnerable to say.

Psych Safety Link: Truth-telling builds trust. When people hear their feelings reflected in a light-hearted way, they feel seen and validated.

5. Know What’s Appropriate

The most important principle of all: appropriateness over laughter. 

Humor can be healing, but it can also be harmful. Sam shared examples of jokes that crossed lines—even unintentionally—and broke trust. He reminded us that appropriateness is relative: it’s not about being "safe" in the HR sense, it’s about being respectful of the emotional safety in the room.

If you mess up? Own it. Apologize. Repair the rupture.

Psych Safety Link: Inappropriate humor can damage psychological safety. But appropriate humor—especially when self-deprecating—can restore it.

The Neuroscience of Laughter

Why does laughter matter so much at work? Neuroscience gives us clues:

• Laughter triggers dopamine and oxytocin, which boost trust and cooperation.
• It lowers cortisol, reducing stress and creating a calm state that improves learning and memory.
• It activates the prefrontal cortex—the part of the brain responsible for decision-making, creativity, and moral reasoning.

When you laugh with others, your nervous systems synchronize. This biological synchrony is what helps teams feel psychologically "in tune." 

What Humor Signals in Culture

In teams with high psychological safety, humor isn’t forced. It’s ambient. It shows up in Slack threads, awkward jokes during retrospectives, and spontaneous memes during Zoom fatigue.

In contrast, humorlessness often signals fear:

• Fear of judgment
• Fear of mistakes
• Fear of being misunderstood

Humor, when safe and shared, is the opposite of fear. It’s freedom. It says, “We’re allowed to be human here.”

When Humor Backfires—and How to Recover

Every culture has stories of jokes that went too far. Some are mildly awkward. Others cause deep harm. In psychologically unsafe teams, humor becomes a weapon: used to mock, to exclude, or to avoid accountability.

Sam offered a key recovery strategy: acknowledge, understand, and repair. Don’t defend your joke. Defend the relationship. Self-awareness and empathy are your strongest recovery tools.

Humor Manifesto

“If there were to be a Humor Manifesto—this is an agile meet up, the first line would be Appropriateness over Laughter. While we value the things on the right, we value the things on the left more. Obviously if you're trying to have fun and make people laugh it's great, when they laugh. If they don't laugh, you're doing great as long as your humor is appropriate…Having the courage to try (humor) is just recognizing that people are grateful when you make an attempt as long as it’s appropriate. Appropriateness over laughter." 

Leaders, Humor, and Psychological Safety

Humor is a leadership skill. Not because leaders should be stand-up comics, but because they shape culture by how they show up.

When leaders use humor:

• They humanize themselves.
• They signal that levity is allowed.
• They model emotional intelligence.

As one participant shared, their CEO once Rickrolled the entire company during a live demo. Not only did the surprise land—it made everyone feel like they were part of an inside joke. That moment lingered in team memory, long after the event faded.

Humor Activities That Build Trust

Want to bring more humor into your teams? Start here:

• "Wrong Answers Only" Brainstorming: Pick a work challenge and brainstorm the worst possible solutions. Laughter unlocks creative thinking.
• Metaphor Mapping: Ask teams to describe current challenges using unrelated metaphors. E.g. “This experience is like trying to bail out a sinking yacht with a paper cup.”
• Ridiculous Retrospectives: Use improv games or meme prompts to spice up team reflections.
• Daily Levity Rituals: Begin meetings with a joke, funny story, or humorous check-in. 

Hiring and Coaching for Humor

While you can’t (and shouldn’t) screen for stand-up comedic talent, you can look for signs of levity in interviews. Look for:

• Storytelling skills
• Comfort with spontaneity
• Self-awareness and keen observations
• Ability to connect with those in the room

As a coach, normalize play. Use humor to unlock stuck conversations and deepen connection.

Final Thoughts: Humor Isn’t Just Fun. It’s Functional.

Humor is a strategic advantage. It creates belonging, reduces fear, and builds shared resilience. When used with intention and care, it makes hard work easier—and worth showing up for.

In Sam Ervin’s words, humor helps us "cut through the tension." And in complex, ambiguous, high-stakes environments, that might be the exact moment we need to move forward.

Psychological safety doesn’t mean perfection. It means presence. Being able to show up, mess up, laugh a little, and keep going—together.

So go ahead. Make the joke. Just make sure it’s human, not hurtful.

Your team might just thank you for it.

Sam Ervin is wildly creative—not just in how he facilitates, listens, and makes people laugh. This is just one of many examples of how humor and creativity, when infused with intention, become not just entertainment, but engagement. Sam's approach models the principles he outlined at the Meetup. Watch the full Agile Boulder MeetUp.

Beyond this Agile Boulder MeetUp, Sam Ervin was a keynote speaker for an RTE Circle where he shared a brilliant example of how he brought humor and team building to life as a Release Train Engineer: his teams didn’t just eat lunch together—they cooked it. He designed an activity around the concept of a live cooking show, asking teams to collaborate in a Food Lab and stage their own version of a “Chopped” episode. Yes, there were ingredients. Yes, there were constraints. Yes, it was hilarious. And yes—these team episodes deserve to go viral. 

If you want to bring psychological safety into your organization but aren't sure where to begin, start here by reading this InKNOWnative Insights: How to Use InKNOWnative’s Step-by-Step Training to Build Sustainable Psychological Safety. 

Citation

Harter, J. K., Schmidt, F. L., Agrawal, S., & Plowman, S. K. (2016). Gallup Q12 Meta-Analysis Report: Ninth Edition. Gallup. https://www.gallup.com/workplace/236441/state-american-workplace-report-2017.aspx
McKinsey & Company. (2021). How to build resilience and navigate disruption with humor. https://www.mckinsey.com/business-functions/people-and-organizational-performance/our-insights/building-resilient-teams-through-humor

Reference Reading
📘 Humor, Seriously: Why Humor Is a Secret Weapon in Business and Life by Jennifer Aaker and Naomi Bagdonas

🍿 Watch Full Recording of Agile Boulder MeetUp: Agile Denver YouTube

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The spark of innovation & knowledge is native to each of us. Empowering organizations to build fearless, high-performing, learning cultures through psychological safety, inclusion, and innovation.

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