Mint Pants, Roses, and Leadership Lessons
This past weekend marked the 152nd running of the Kentucky Derby. I’m not a huge horse racing fan, but April and I had the opportunity to attend the Derby four years ago, and it’s held a special place with me ever since.
It’s hard to fully describe the experience until you’re there. The spectacle lives up to the billing and if you ever have the pleasure of experiencing the Derby in person, be sure to also attend the VIP event hosted by The RK Group at Churchill Downs. The traditions, the energy, the fashion, the crowd of over 150,000 people, it’s a two-day celebration that all builds toward what’s known as the fastest two minutes in sports.
Since this year’s Derby overlapped with my most recent board meeting for the University of Oregon Alumni Association, I figured I’d blend the two. On Saturday morning, while addressing the board in Portland (the City of Roses), I showed up in mint green pants and a patterned rose shirt and connected a few lessons from the Derby (The Run for the Roses) to leadership.
Connecting the Kentucky Derby to lessons in leadership brought smiles at the OU Board meeting.
Stand the test of time
For something to last over 150 years, it can’t rely on tradition alone. The Kentucky Derby has held onto its core (the pageantry, the rituals, the history) while continuing to evolve. It’s a reminder that great organizations honor where they’ve come from while staying open to change. Leaders have to balance both. Too much tradition, and you get stuck. Too much change, and you lose your identity.
Speed matters
The Derby is over in about two minutes, yet it fuels days of excitement and preparation. It’s a reminder that short bursts of focused effort can have a big impact. In leadership, we often talk about long-term strategy, but there are moments where speed, decisiveness, and execution matter just as much. When the opportunity is there, you have to be ready to move fast.
Community creates meaning
More than 150,000 people attend the Derby each year and many more gather across the country to watch on tv. It’s not just about the race. It’s about the shared experience. The connection. The tradition of being part of something bigger. The same is true in our organizations. Culture is built when people feel like they belong to something that matters.
Don’t be afraid to stand out
There’s nothing subtle about Derby fashion. Big hats, bold colors, wild patterns. It’s part of what makes the event memorable. In leadership, we don’t talk about this enough. Standing out in how you show up, how you communicate, and how you lead can create energy and leave a lasting impression.
Finally this year added another meaningful moment. For the first time in the Derby’s history, a woman trainer, Cherie DeVaux, won the race. A powerful reminder that progress continues, even in the most tradition-rich environments. When we create opportunities for new voices and perspectives, we move forward in ways that strengthen our communities.
The Kentucky Derby may only last two minutes, but the lessons extend far beyond the track.
As leaders, we’re constantly balancing tradition and change, speed and patience, individuality and community.
So how are you showing up in your own “run for the roses”?
P.S. Create a community of like minded leaders that stands the test of time! Join us at our MIBE Workshop May 12th - 13th.
