Kevin Toler, Partner & Private Wealth Advisor, Hill Island Financial
The Problem
Kevin was leading a team that had started to outgrow its structure. What had once been a small, manageable crew was a lot bigger. The pace of change was picking up, but the trust and cohesion were lacking. Turnover crept in. Morale dipped. He felt it in the silence, in the way conversations with his team had shifted. And under it all, there was something harder to admit. He felt alone as a leader.
“I was exhausted. And the real issue was, I felt lonely. I was trying to lead a growing team without a real partner to reflect with or guide me.”
The Shift
Kevin’s team and I met regularly to work through team dynamics, communication breakdowns, and personal leadership roadblocks. I served as a sounding board, a strategist, and a collaborator. Not from the sidelines, but alongside him. Every conversation was tied to the people on his team, the goals they were reaching for, and the kind of leader he wanted to be.
“The thing that stands out the most is that I had someone in my corner, invested in my success, pushing the company to get better”
The Strategy
We focused on two things: building internal clarity and external connection. Kevin worked on refining how he communicated, how he supported his team, and how to create consistency in leadership even as the company scaled. Together, we introduced new language to talk through challenges and we focused on individual personalities and how they responded to directives. And we repeated it. Not once. Not twice. But consistently, over time.
“She got in the trenches with us. She didn’t deliver a talk and disappear. She stayed in it. Again and again.”
The Impact
Over the course of our work together, Kevin’s team grew from three to ten. Revenue more than tripled. And the pressure that once felt overwhelming was being carried with confidence.
The culture shifted too. The language we built around feedback, personalities, and leadership tone became part of how the team worked together. The loneliness that once made leadership feel heavy was replaced by clarity, rhythm, and trust.
“There are strategies we still use today. Things that became part of our everyday language and culture.”
The Takeaway
Kevin needed someone who would walk with him, challenge him, and make the hard parts easier to face. That’s what partnership looks like in real leadership development.
“She doesn’t just teach leadership. She’s lived it. And when she chooses to work with you, she shows up fully. The results speak for themselves.”