Evidence Leadership Group

This week, I sat down with Colonel Orlando Lilly, and what stood out to me wasn’t just his career—it was the moment that started it all. As a 10-year-old kid, he was fighting for his life in a hospital after being seriously injured. A police officer showed up and stood there, emotional, present, and fully invested in a child he didn’t know. That officer didn’t have to be there. There was no assignment, no expectation. But that moment of compassion changed everything. Lilly told me that’s when he decided he wanted to become a police officer. And decades later, he fulfilled that promise.

What hit me during our conversation is how often we overlook the power of those moments. We focus on rank, credentials, and authority—but people don’t remember that. They remember how you showed up. Lilly made it clear that leadership isn’t about the position you hold, it’s about the presence you bring. That officer didn’t lead with authority, he led with humanity. And that’s what stuck.

We also talked about something I think a lot of supervisors get wrong—what “positive leadership” actually means. Lilly challenged the idea that leadership automatically equals something good. He explained that real leadership isn’t claimed, it’s attributed. You don’t become a leader because you say you are—you become one because of how people experience you over time. He shared how even early in his life, before he had rank or title, he focused on lifting others up. And because of that, people naturally looked to him as a leader.

Another major takeaway for me was the shift from transactional to relational leadership. In policing, it’s easy to fall into a routine—give instructions, get compliance, move on. But Lilly pushed the idea that the work has evolved. It’s no longer just about enforcement; it’s about connection. He used a simple example—on a traffic stop, you can go straight to business, or you can take a moment to engage the person as a human being. The outcome might be the same, but the experience is completely different. And over time, those experiences shape trust.

We also got into emotional intelligence, and Lilly didn’t sugarcoat it. He talked about the importance of self-awareness and self-regulation, especially when you’re operating in environments where emotions can work against you. One thing he said stuck with me—when you operate from emotion, people stop hearing you. That’s something every leader needs to understand. Emotional intelligence isn’t something you either have or don’t have—it’s something you build, intentionally.

And toward the end, he shared a leadership model that really resonated with me—the idea of being a gardener, not a chessmaster. Too many leaders try to control everything, trying to position people and dictate outcomes. Lilly sees it differently. He believes in creating the conditions for people to grow, investing in them, and understanding that you might not always be the one who sees the results. But that doesn’t make the work any less important.

What I took from this conversation is simple: leadership shows up in the moments when you don’t have to act—but choose to anyway. That’s where trust is built. That’s where influence starts. And more often than not, those moments shape more than we’ll ever realize.

If this challenged how you think about leadership, you need to listen to the full conversation.