Gregg Popovich. Photograph by Soobum Im, USA TODAY Sports

Gregg Popovich, the legendary basketball coach, has retired from coaching and will be moving into a new role as the San Antonio Spurs’ president of basketball operations. I have long been a fan of Coach Pop, who has led his teams to five NBA championships and an Olympic gold medal. All of that is remarkable, but what I loved most about Pop was his playful leadership style. He coached his teams one deadpan zinger at a time. He was known for being blunt, self-deprecating, and hilarious. He would roast his players in film sessions, crack dry jokes in tense moments, and drop absurd one-liners when things got too heavy. Humor wasn’t a gimmick for Coach Pop. It was how he connected.

Golden State Warrior Draymond Green, who won a gold medal with Coach Pop, said, “You get this wall that everyone sees. And it just appears as if he’s this mean old man. And he’s the complete opposite. The nicest person you ever want to be around. He cares about people so much.”

When was the last time you laughed at work? Not a chuckle during a regular meeting, but an actual spontaneous, full-body laugh? When did you last go off-script in a 1:1, riff in a team meeting, or suggest something unexpectedly weird just to see what happened?

We’ve all absorbed some version of this myth: good leaders are stoic, measured, serious, and unflappable. They understand that everything requires effort and struggle. The truth is, some of the most effective leaders I’ve ever known are the ones who know how to bring levity into the room. These leaders, like Coach Pop, recognized that playful laughter builds trust. They used humor to cut through the defuse tension and connect with their teams on a human level.

In high-stakes environments, humor is pressure relief. When leaders shift from seriousness to spaciousness, something opens up. Playfulness becomes an access point to presence, connection, and flow.

Playful leaders say, “Let’s try something,” instead of, “Let’s get this exactly right.” It shows up when you laugh in a moment of tension, and everyone exhales. It shows up when you’re present enough to improvise rather than perform. Playfulness and humor won’t erode your credibility. They amplify your presence. They make you real. And people follow real. Just ask the numerous current and future Hall of Fame players and coaches who Gregg Popovich led.

The research backs it up

Don’t just take my word for it.

• Humor builds trust and connection. Laughter strengthens social bonds and builds trust among coworkers, especially when leaders initiate it.
• Play reduces stress. Humor triggers dopamine and reduces cortisol, increasing emotional resilience and reducing burnout.
• Playfulness fuels creativity and innovation. It’s not just about having fun, it’s about creating the container for people to feel safe to take creative risks and solve complex problems. This can motivate your team to be more innovative and productive.
• Humor makes leaders more effective. Leaders who use inclusive and self-aware humor are rated as more competent and confident than those who don’t.¹

Humor changes how people feel at work. And how people feel at work changes how they work.

“But I’m not funny…”

Good news: you don’t have to be.

This isn’t about dropping one-liners or adding a “funny quote” to your next all-hands. If that’s not your style, don’t force it. Nothing kills the vibe like cringy, try-hard humor. Rather, it’s about making room for spontaneity. It’s about revealing what you’re really thinking—even if it’s a little weird. It’s about being able to laugh at yourself when something goes sideways. Humor is a mindset shift, not a skill you have to master. You don’t need to be funny. You just need to be real.

Of course, there are different forms of humor, and not all of them are effective. Some can be downright destructive. Researchers have identified four core distinct humor styles: affiliative, self-enhancing, aggressive, and self-defeating.² Of them, affiliative humor—good-natured, inclusive joking focused on enhancing our bond with others—can be extraordinarily effective in leadership. Self-enhancing humor—the ability to laugh at oneself in a constructive, non-detrimental manner—is also powerful in leadership, but its effectiveness can vary by culture. In most U.S. workplaces, self-enhancing humor has been shown to encourage creativity and reduce anxiety.³ A review of the academic literature found that “self-deprecating humor, specifically willingness to make humorous comments about personal weaknesses, was perceived as transparent communication and was more likely to yield trust from followers and indirectly influence followers’ perceptions of leader effectiveness.”

On the other hand, aggressive humor—put-downs, belittling others, teasing, and negative sarcasm—undermines psychological safety (even when the “other” being denigrated is not in the room). Self-defeating humor—jokes directed at oneself as a defense mechanism or to seek the approval of others—can undermine a leader’s authority in the workplace.

Use humor to lift the room, not tear someone down. What might seem like harmless teasing from a life-long friend can feel like ridicule from your boss. As standup comedians say: “Always punch up. Never punch down.” As a leader, you have more power than you think. Wield it with care.

The real risk is seriousness

Let’s be honest: nobody wants to follow a joyless leader. If your presence signals, “Everything is fine. I’ve got this all figured out. Please don’t show me anything messy,” your team will take the hint. They’ll shut down their off-the-wall ideas, their honest feedback, their full selves.

Ditch the “Serious Leader” costume. Show up as the real you—the one who’s learning, laughing, improvising, and not afraid to be a little ridiculous. That’s who people will trust. Because when you loosen up, something powerful happens: people feel safe. And safe people do exceptional work.

And as for Gregg Popovich? He transitioned into his new role as Spurs team president in typical Coach Pop style. At the press conference introducing the Spurs new permanent head coach, he took off his track jacket to reveal a t-shirt that read “El Jefe” and “Señor Popovich, President of Basketball Ops.”

Gregg Popovich plays a joke on Shaquille O'Neal

1. Brooks, A. W. (2017, January 11). Research: Cracking a joke at work can make you seem more competent. Harvard Business Review. Accessed April 14, 2025. ↩

2. Heintz, S., & Ruch, W. (2019). From four to nine styles: An update on individual differences in humor. Personality and Individual Differences, 141, 7-12. https://doi.org/10.1016/j.paid.2018.12.008 ↩

3. Romero, E.J., & Cruthirds, K.W. (2006). The Use of Humor in the Workplace. Academy of Management Perspectives, Vol. 20, No. 2. https://journals.aom.org/doi/10.5465/amp.2006.20591005 ↩