Finding the Funny in Winning: Why Great Leaders Celebrate Failure
At the Texas Nursery & Landscape Association (TNLA) conference, we explored a surprising path to leadership success: finding the humor, humility, and growth in failure.
In our session, Finding the Funny in Winning, we unpacked a powerful truth: teams don’t thrive when leaders expect perfection. They thrive when leaders make it safe to take risks, admit mistakes, and keep moving forward. And when failure becomes a learning opportunity instead of a shame spiral, that’s when the magic happens.
Celebrate Failure? Really?
Yes, really. Fear of failure is one of the biggest killers of momentum inside organizations. It leads to indecision, finger-pointing, and silence when transparency is most needed. But when you normalize failure and laugh a little along the way, your team becomes more resilient, innovative, and committed.
The Learning Zone
Borrowing from Harvard Business Review’s “Learning Zone” concept, we taught that failure isn’t the opposite of success—it’s a part of it. Encouraging your team to bring forward mistakes leads to better decision-making and fewer repeat errors. It’s not about glorifying failure—it’s about debriefing it, learning from it, and improving because of it.
Lead From the Front
As a leader, you set the tone. When you openly admit your own missteps, you create a culture where learning is safe and shame-free. We call this “leading from the front.” It’s not about having all the answers—it’s about modeling the mindset and swagger that says, “We get better together.”
Failure Builds Resilience
Failure isn’t just something to survive. It builds grit. When you celebrate the courage it takes to try and fail, your team becomes more persistent and adaptive. They learn how to bounce back, adjust, and keep going. That’s how you build long-term results—and long-term leaders.
Innovation Comes from Mistakes
Many of the greatest breakthroughs in history happened because something didn’t go according to plan. When you remove the stigma of failure, your team gets bolder. They experiment. They suggest new ideas. They solve problems creatively, without fear of being punished for trying something different.
Promoting Accountability (Not Excuses)
Celebrating failure doesn’t mean avoiding accountability. Quite the opposite. When people feel safe admitting mistakes, they’re more likely to take ownership of them. That’s when true accountability happens—not from blame, but from growth.
Build a Team That Laughs Together
When teams share failures and debrief them together, it creates connection, strengthens culture, and even lightens the emotional weight of challenges. Whether you gamify learning or crack a joke after a flubbed proposal, shared humor can be a bonding force that keeps morale high and teams united.
Final Thought: Win With Swagger, Not Perfection
True leadership isn’t about being flawless. It’s about creating a team that feels confident enough to take risks, strong enough to own mistakes, and humble enough to laugh along the way.
So, the next time something goes sideways? Find the funny. Then find the lesson. That’s how you keep winning.