Why Fun at Work is a Leader’s Secret Weapon
November 8, 2025
One of the joys of leadership is deciding what kind of culture you want and creating that environment for yourself and your team. The leader sets the tone for workplace culture.
Fun is Sorely Missing from the Majority of Workplaces
According to a survey by The Conference Board Inc., 53 percent of Americans are currently unhappy at work. That’s a staggeringly depressing statistic. Over half of us don’t like what we do each and every day.
Work can easily turn tedious, draining, and stressful if you’re not paying attention and actively working on the culture. The best leaders are intentional about injecting fun into the workplace.
“People rarely succeed unless they have fun in what they’re doing,” according to legendary writer and teacher Dale Carnegie.
When you take the time and effort to bring joy into your office, great things happen. Taking people's minds off work for a while causes them to feel rejuvenated. In fact, sometimes not working is the most productive thing your team can do together.
It’s been estimated that you will spend roughly one-third of your life at work. Life is too short not to enjoy the workplace. It’s paramount for employers not only to accept a fun work environment but to create a fun work environment.
The Best Leaders Encourage Fun in the Workplace
The primary reason most people feel their workplace lacks joy is simple: poor leadership. If a company’s leaders don’t value joy, it will be difficult to find joy in the company.
Today, so many bosses are pressured to increase revenue, boost efficiency, handle unending meetings, and clear out that inbox full of emails. It’s easy for leaders to have blurred vision that can’t see beyond the to-do list. There’s something just as important, if not more important, than the daily tasks: being positive and lighthearted.
Effective leaders have fun. They allow surprises. They take time to chat with others. They value relationships with team members more than to-do lists.
The best leaders don’t just allow fun; they cause it.
If you’re a leader, you must spend a some of your time purposefully enhancing the environment of the organization. Author Scott Berkun conveyed this sentiment well when he wrote, “Every CEO is, in fact, a Chief Cultural Officer. The terrifying thing is it’s the CEO’s actual behavior, not their speeches or the list of values they have put up on posters, that defines what the culture is.”
A Fun Workplace Improves Productivity
Fun at work isn't just a morale booster. A recent study by economists at the University of Warwick found that happiness triggered by fun or humorous experiences made employees 12% more productive, as they completed tasks faster without sacrificing quality. Meanwhile, a sweeping meta-analysis of 225 studies revealed that happy workers deliver a whopping 31% higher productivity on average.
As advertising and business leader David Ogilvy said, “Where people aren’t having any fun, they seldom produce good work.”
Leaders who spark joy aren't playing around; they're setting up an environment that can boost performance.
The Surprise Trick-Shot Challenge That Boosted Our Work Culture
At the Blue Compass Digital Marketing Agency, our leaders take fun very seriously. We're purposeful about adding enjoyable experiences to our work days. For instance, we recent set up a surprise trick-shot basketball challenge for our team.
Traffic cones barricaded our parking. Smack in the middle stood the basketball hoop. Up on the roof of our two-story office? A neat row of basketballs, ready for battle.
At Blue Compass, we treat fun like it’s quarterly earnings—non-negotiable. Our leaders laugh at their own screw-ups. Managers don’t take themselves too seriously. Again, we believe that the best leaders don’t just allow fun, they cause it.
So naturally, I announced a surprise rooftop trick-shot challenge: if any team member can sink a 60-footer from the roof, everyone gets a bonus.
Cue gasps, laughter and cheers. I guided them up to the roof in groups throughout the sunny October afternoon. “What an incredible moment of work culture goodness and team unity,” I thought to myself. “It’s going to be amazing when someone hits this shot.”
While I was having a great time watching my team members take shots across the parking lot (and our CFO, Cary, chasing down basketballs and tossing them back up to us on the roof), slowly, my smile started to fade. I assumed it would take a couple dozen people until someone sunk this shot. As team member after team member launched their basketball into trees and dangerously close to parked cars, I realized I may have made this challenge way too difficult.
The joyful, inspirational video I’d envisioned was slowly turning into a blooper reel of despair.
Finally, our very last team member, Jeff, stepped up for his turn. I tossed him a basketball; he eyed the hoop and took his shot. The ball arced through the air, bounced once, and swished perfectly through the net. Everyone erupted in cheers! Our team was thrilled. It was a blast seeing everyone’s shock and delight as someone finally nailed it.
To this day, people accuse me of faking the shot or using AI to doctor the video. But it’s real! The final shot was a success.
And yes, we gave bonuses to everyone.
I posted the video online and got a great response. Not only did our team love the experience, but so did everyone else. Well, almost everyone. Some were upset that we’d do something so “unsafe” as launching basketballs from the office roof. Some called it an incredible display of great company culture; others called it an incredible OSHA violation. But that’s okay; you can’t please everyone.
Leaders Have the Opportunity to Make Work Fun
Perhaps my favorite part of being a leader is the chance to build a wonderful, positive, fun, weird, joyful company culture.
Yes, many factors influence it, but as a leader, your impact is significant. You don’t need to risk OSHA violations on your office roof to build a great culture, but you can make it positive and supportive.