💯 If We Couldn’t Fail: Four Questions for 2025 with Ryan Leak

At NADA 2025, we gathered in the vibrant city of New Orleans not just to celebrate the incredible work being done by dealers nationwide but to be inspired to reach even greater heights. NADA has always been about more than just cars—it’s about people, legacy, and shaping the future of communities across the country. On the main stage, Ryan Lea delivered a powerful, heartfelt message that resonated deeply with this mission.

With his signature humor, undeniable energy, and thoughtful storytelling, Ryan challenged every dealer, manager, and leader in the room to step into the new year with intention, courage, and a willingness to fail forward. His talk, anchored around four transformative questions, wasn’t just a motivational boost—it was a call to action to elevate ourselves and our industry.

What’s It Like to Be on the Other Side of Me?

Ryan opened by asking the kind of question that stops you in your tracks: “Have you ever thought about what it’s like to be hired by you? Managed by you? Married to you?”

Self-awareness, Ryan explained, is the cornerstone of next-level leadership. Too often, we assume our intentions translate perfectly to those around us—but they don’t. “Next-level leaders walk into the room assuming they might be the person who needs to grow,” he said.

Do or Do Not, There is no Try:

• Ask for Honest Feedback: Regularly invite your team to share candid input on how you can better support them.

• Approach Conflict with Empathy: Recognize that difficult people often have difficult stories—and so do you.

• Challenge Your Comfort Zone: Assume you have blind spots and actively seek to address them.

How Can I Be Intentional?

“Great leaders don’t happen by accident,” Ryan told the audience. Intentionality—clear communication, consistent follow-up, and humility—is what separates leaders who inspire from those who merely manage.

Leaders, Ryan said, are also the “Chief Repeating Officers” of their organizations. “Don’t assume everyone knows your values or priorities. Say them again. And again. And again.”

Intentional Steps:

• Over-Communicate Expectations: Clarity prevents confusion. Be specific, repeat often, and verify understanding.

• Seek Feedback Constantly: Don’t wait for annual reviews—ask your team regularly how you can improve.

• Admit When You’re Wrong: Use language like “I could be wrong, but…” to create space for dialogue and growth.

Who Can I Pave the Way For?

Ryan’s success is a testament to the power of mentors and champions. From teachers to first bosses, his journey was shaped by people willing to take a chance on him—and he urged the audience to do the same for others.

“You’re not just building a great business,” Ryan said. “You’re building great people. And when you build great people, the business takes care of itself.”

Rent a Steam Roller?

• Invest in Potential: Look for someone on your team who could thrive with the right support—and be their champion.

• Create Opportunities: Give your team members a shot at challenges they might not feel ready for.

• Pay It Forward: Ask yourself, “Who will be in this room five years from now because of me?”

What Would I Do If I Knew I Couldn’t Fail?

Ryan shared a deeply personal story of “chasing failure,” from emailing NBA teams for tryouts to landing a workout with the Phoenix Suns. His takeaway? Fear of failure often keeps us from achieving our biggest successes.

“When we take risks, we might fail,” he said. “But chasing failure will always take you further than chasing comfort.”

“Just Do It”

• Think Boldly: Write down the ideas you’ve dismissed as “impossible” and take one step toward making them real.

• Redefine Failure: Treat setbacks as lessons, not endings. Every great leader has failed—many times.

• Encourage Courage: Foster an environment where your team feels safe taking calculated risks.

The NADA Spirit in Action

Ryan closed with a challenge: “What would you do if you knew you couldn’t fail?”

This question goes to the heart of what NADA represents: a relentless belief in the power of people and businesses to create lasting change. Dealers are the backbone of their communities, and their leadership has the potential to ripple far beyond the walls of their stores.

NADA 2025 isn’t just an event—it’s a movement. Let Ryan’s four questions guide you as you move boldly into the new year. After all, as Ryan said, “You’ll never know if you’re the exception to the rule unless you try something exceptional.”

So, dealer fam, what will you do if you couldn’t fail?