When Leadership Means Letting Go

By Casey Cunningham | May 12, 2025 | From Our CEO

Are You Avoiding a Decision That’s Slowly Crushing You?

Years ago, I faced a decision that made my heart ache.
A promising sales student was struggling—late to class, falling asleep, ignoring feedback. He had talent, but no discipline. And I kept giving him chances, hoping he’d turn it around.

But as a leader, I knew I couldn’t protect potential over performance forever. I had to act.


The Trap

We think kindness means protecting people from discomfort. But when we avoid tough decisions, we’re not helping—we’re enabling.

That’s not leadership. It’s fear.

Everyone around us sees what we tolerate. I had a whole classroom looking to me, measuring what kind of culture I was willing to create. Would I let one person’s behavior define the standard?

The longer I waited, the heavier it felt.


The Fix

I made the decision. I let him go.

He was upset. So was I. My heart hurt, but my conscience was clear.
Fast forward 10 years—I ran into him at a party. He came straight over, tears in his eyes.

“That day changed my life. I’m in executive leadership now… because you forced me to face the truth.”

That moment proved it: Accountability isn’t cruelty. It’s clarity. It’s leadership. And it can transform lives.


Challenge

What decision are you dragging your feet on—because it feels too hard?

Whether it’s a team member, a habit, or a standard you’ve been avoiding… today is the day. Lead with heart, but lead with strength. The weight you’re carrying? It lifts fast when you act.

Listen to the episode and tell me your reset!


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