The Unexpected Thing That Saved My Client's Job
How would you feel if your boss was a 6’6”, heavy-set guy who barely cracked a smile, mumbled through his presentations and seemed to take himself very seriously?
A little intimidated? Yeah, me too.
Years ago, early in my coaching career, I got a call from a client asking if I could help his colleague—someone who was on the verge of losing his job.
Joe was the divisional CFO of a multinational company, based in New York. His boss, the CFO of the parent company, worked out of Germany.
The first time I met Joe, I instantly understood why people found him intimidating. Given his physical stature, he seemed to unfold out of his chair and his hand shake was conducted with an enormous hand. Everything about him seemed imposing - his serious manner and his low, deep voice. Even though he was actually a kind, sweet, self-deprecating man, he still gave off a "don’t mess with me" vibe.
Here’s the thing: he had no idea that this was how he came across. He was completely unaware that his size, demeanor, and communication style intimidated his team and colleagues.
(Sidnote: This is incredibly common. Many of the leaders I coach don’t realize how they come across, how their behavior is interpreted, and how it impacts their careers. I’ve helped hundreds of leaders make small shifts that yield major results.)
When I asked Joe if he ever used humor in his presentations, he gave me a confused look and said, “No, should I?”
"Absolutely!" I told him.
Why? Because when you’re a towering figure talking about serious financial topics, a little humor goes a long way. If he could lighten the mood just a bit, he’d make it easier for people to engage with what he was saying.
I explained that adding some humor would:
Make people enjoy his presentation and appreciate his perspective
Help his audience absorb and retain the material
Put his team at ease
Help him build stronger connections
Fast forward two months: Joe was no longer on the ‘potential replacement’ list. Eight months later? He got promoted—taking over his boss’s role as CFO of the entire company!
Now, did humor alone get him that promotion? No, of course not. We also worked on making sure his emails were typo-free - even though these typos were culturally acceptable within the company. I helped him realize that his actions needed to be ‘above reproach’ to get ‘out of the dog house’.
He also paid attention to speaking more clearly (especially important when your boss is a non-native English speaker). These small changes made a huge difference—not just in saving his job but in elevating his career and personal brand.
If you want to connect with your team more effectively, adding a little humor is a great place to start.
4 Ways to Use Humor at Work to Connect With Your Team
1. Use self-deprecating humor to show relatability
Self-deprecating humor, when used thoughtfully, makes leaders more approachable. It signals confidence and humility—two qualities that build trust and followership.
A study published in Frontiers in Psychology found that leaders who use self-deprecating humor can significantly reduce employee silence by fostering high-quality leader-colleague exchanges. When people see you as human, they’re more likely to engage openly with you.
2. Share stories and insights that reveal authenticity
Telling personal stories—especially about your own mistakes or challenges—creates connection. When leaders show they’re real people, rather than untouchable authority figures who haven’t had to work through challenges, they become more relatable.
For example, I often share a story about my first job as an investment banking analyst. My boss found a word typo in a presentation that I had created for a group of 15 people. He threw the deck at me in front of everyone and said he didn’t trust the numbers in the deck and demanded that I ‘recrunch’ them.
Guess what? I never had a typo again in a presentation, but I also never trusted my boss again to treat me with respect. (That experience also taught me exactly what kind of culture I never wanted to experience or create again.)
3. Use humor strategically to address tension
Humor is an amazing tool for defusing tension, especially during tough conversations or stressful times. A light joke—at the right moment—can make difficult topics feel less daunting and encourage open dialogue.
For example, if your company is rolling out a new software system, you could say something like, “I know learning a new platform is about as fun as a root canal, but we’ll get through it!” Or even, “Five bucks on the company tab at Starbucks every time someone finds a bug.” (And then actually follow through by tracking how many bugs you find and putting it on the tab!)
These small moments of levity acknowledge the challenge without letting it take over the room.
4. Add lighthearted icebreakers and personal anecdotes
I know, I know—people love to roll their eyes at icebreakers. But they work. And they don’t have to feel forced or contrived.
Instead of asking everyone to go around the room and share their life stories, try casually adding a brief, personal anecdote before diving into your meeting.
For example, I might ask if there are any weekend warrior pickleball players or ask for suggestions for good cycling areas nearby. Personal touches like these make you more relatable—and who knows, you might find common ground with someone new!
Humor and Authenticity: The Leadership Superpowers You Need
Bringing humor and authenticity into your leadership style isn’t about being a stand-up comedian—it’s about being real, relatable, and fostering a culture of trust.
Research consistently shows that leaders who use humor effectively, share personal stories, and engage authentically build stronger connections and drive better results. The key is balance—using humor to engage, not distract.
When leaders show up as real people, they inspire their teams to do the same. And that’s how you create a workplace that’s not just productive—but actually enjoyable.