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The Founder’s Dilemma: When Humility Unlocks Growth

February 18, 2024

A few years ago, I was mentoring a promising founder—brilliant, driven, and relentless in his pursuit of success. He had built a solid product, assembled a strong team, and secured early traction. Yet, something was holding him back, and he didn’t even see it.

He felt the need to have all the answers.

One day, during a strategy session, I noticed his team hesitating to challenge a key decision. Their body language spoke volumes. When I probed, one of them finally admitted:

“He’s already decided. We know he won’t change his mind.”

The founder looked surprised. In his mind, he was leading decisively. To his team, he was shutting down discussion.

Later, in a one-on-one, I asked him, “What if the best idea in the room isn’t yours?” He paused. It was a question he had never considered.

That moment sparked a shift. He started making small but powerful changes—anonymous “Ask Me Anything”s to encourage open feedback, reverse mentoring to learn from his younger team members, and pre-mortems before big initiatives to uncover blind spots. He even began writing reflection notes after investor meetings, capturing key learnings instead of just defending his position.

The impact? His team became more engaged. Innovation flowed more freely. And when the company scaled, it wasn’t because of one person’s brilliance, but because he had created an environment where everyone could contribute their best thinking.

Humility isn’t about self-doubt. It’s about recognizing that the best ideas don’t always come from you—and that true leadership lies in empowering those around you.

Take a moment to reflect: Where in your journey can you step back, listen deeper, and create more space for growth? Often, the breakthroughs we seek don’t come from pushing harder, but from embracing the quiet power of humility.

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Posted in: Riff Tagged: humility, integrity, learning, let go

No matter our age, our circumstances, or abilities, each of us can create something remarkable with our lives - Joseph B. Wirthlin
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