Empathetic Leadership with Jevon Wooden: A Story of Grace and Growth
Vulnerable leadership isn’t about weakness—it’s about the strength that comes from authentic experience.
Every so often, you meet someone whose story stays with you—someone who embodies what empathetic leadership truly looks like. My recent conversation with Jevon Wooden reminded me of the redemptive power of second chances and the quiet strength of empathy. This is a powerful example of empathetic leadership with Jevon Wooden.
Before he became a decorated Army veteran, an executive coach, and a voice for transformational leadership, Jevon was a 17-year-old facing jail time. Arrested and incarcerated at a pivotal age, his future could have easily gone the way of statistics. But in a moment that would shape his entire trajectory, he stood before a judge who chose grace over judgment. This judge looked past Jevon’s circumstances and into his potential. Rather than define him by his worst mistake, she gave him a chance to rewrite the narrative. That single act of empathy—by someone in authority—set into motion a lifetime of service, growth, and purpose. This moment would later shape his understanding of vulnerable leadership—how grace from those in authority can transform lives.
How Vulnerable Leadership Transforms from Within
Jevon doesn’t shy away from that chapter of his life. In fact, it’s what makes his message hit so deeply. During our conversation, he reflected on the internal work that followed—how he had to learn to love himself, not just fix his behavior. “I didn’t love who I was,” he told me candidly, “because I wasn’t doing the internal work.” Indeed, that level of honesty, from a man who now coaches executives and speaks on leadership stages, is rare. And it’s what gives him credibility.
Throughout our conversation, one truth kept surfacing: leadership begins within. You can’t lead others if you haven’t first learned to lead yourself. Jevon’s transformation didn’t begin with a certification or a business plan—it began with forgiveness, reflection, and a new story. Today, that’s exactly what he helps others do: rewrite the stories they’ve been telling themselves. So many professionals, he says, carry limiting beliefs formed by past mistakes or the voices of others. Jevon’s work is about helping them challenge those narratives and discover who they really are beneath the noise. This approach embodies the essence of vulnerable leadership: helping others rewrite their stories by first being authentic about your own journey.
Why Vulnerable Leadership is the Strongest Kind
As we spoke, we kept coming back to the importance of joy and purpose in our work. “Making an impact and having fun—you can’t beat that,” Jevon said with a smile. I couldn’t agree more. I chimed in with my own thought: “In order to have impact, you better enjoy what you’re doing. Because if you’re just going through the motions, it’s not going to work.” When your work centers around developing people—whether you’re a coach, a leader, or a parent—joy isn’t a luxury. It’s fuel. And people can tell the difference between someone who’s fully alive in their work and someone who’s simply clocking in.
But the heart of Jevon’s message—and the thread that ties his whole journey together—is the call to lead with empathy. He believes, as I do, that we’re living in a new era of leadership. The command-and-control model is crumbling. People aren’t looking for perfect leaders; they’re looking for present ones. “People don’t want perfection,” he told me. “They want authenticity.” That means showing up human. Listening with your heart. Leading with love, not ego. This is vulnerable leadership in action—showing up as a whole person, not a perfect facade.
During our exchange, I shared something that’s become a personal mantra: “The greatest leaders I know have a little limp. They’ve been through something. That’s what gives them credibility.” Jevon wholeheartedly agreed. The leaders who’ve endured pain—who’ve faced rejection, disappointment, failure—are the ones who extend the most grace. Their empathy isn’t theoretical. It’s born out of experience. And it’s exactly what makes people trust them. This is the core of vulnerable leadership: credibility earned through shared human experience.
The Power of Vulnerable Leadership in Action
Jevon is a living example of how one moment of grace can change the course of a life—and how leaders who remember that moment often spend their lives paying it forward. Whether he’s coaching clients, speaking on stage, or mentoring the next generation, he leads from a place of humility and hope. He doesn’t just talk about transformation. He is the transformation.
Empathetic leadership isn’t soft. It’s the strongest kind there is. It sees what’s possible in people before they see it in themselves. It lifts, listens, and lets people grow. And as Jevon’s story reminds us, sometimes all it takes is one person who chooses to see the potential in us instead of the past.
So here’s to the leaders who walk with a limp. Who know what it means to fall and get back up. Who choose empathy over ego, presence over perfection, and grace over judgment. The world needs more of them. Jevon Wooden is one of them.
And I’m grateful the world gets to hear his voice.
