Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 223 of The HaltingWinter Podcast
Brought to you by Zencity and Tyler Technologies
What does it take to become a city manager? For Dylan Ward of Henderson, Kentucky, the journey started with a box of Legos.
As a kid, Dylan loved to build, problem-solve, and create. That curiosity led him to study civil engineering. But he soon realized he didn’t want to spend his life behind a computer screen designing projects in AutoCAD. He wanted to be where the action was—out in the field, working with people, and seeing ideas come to life.
That curiosity, combined with his leadership experience running a fraternity at Western Kentucky University, led him into local government. At first, Dylan didn’t even know what a city manager was. But as he rose through the ranks in Henderson, from Engineering Assistant to Project Manager to Assistant City Manager, he discovered a role that perfectly blended technical skill with leadership.
In our conversation, Dylan shares the pride of driving past projects that will shape his community for decades: sidewalks, parks, lighting, and multimillion-dollar infrastructure upgrades. Unlike private-sector engineering, where projects may be distant or abstract, local government gave him something tangible: “I can drive down any road and say, yeah, that was something I worked on.”
Dylan also opens up about one of Henderson’s most successful public-private partnerships: transforming a failing nine-hole municipal golf course into a thriving regional 18-hole course that sparked new neighborhood development. It’s a reminder that local government doesn’t just manage—it creates opportunities for economic growth and community pride.
Perhaps the most moving part of Dylan’s story isn’t about public works at all. It’s about family. In 2021, Dylan and his wife planned to leave Henderson for mission work in El Salvador. Instead, they found themselves living six months in the Ronald McDonald House in Cincinnati as their newborn son underwent multiple open-heart surgeries.
That season reshaped Dylan as a leader. “What I went through with my son has allowed me to relate better to people,” he says. “Employees aren’t just workers—they’re people with their own stories and struggles.”
Dylan also shares the impact of mentorship. His longtime leader, Buzzy Newman, not only hired and mentored him but later stepped aside to let Dylan become City Manager—then returned as his assistant to ensure a smooth transition. It’s a remarkable example of humility and healthy succession planning in local government.
Listen to the full conversation: Dylan Ward: From LEGO Sets to City Streets
This episode of The HaltingWinter Podcast is made possible by our sponsors, Zencity and Tyler Technologies, who help local governments across the country better serve their communities.
Zencity
Local government leaders don’t have the luxury of guessing what residents think. Zencity helps you cut through the noise and hear directly from your community—not just the “same ten people.” By gathering real-time feedback across every neighborhood and demographic, Zencity gives you the insight to make decisions with clarity, confidence, and legitimacy. It’s about turning community voice into community trust.
Discover how Zencity helps leaders listen at www.zencity.io.
Tyler Technologies
Behind every thriving community is a city that runs well. Tyler Technologies is the nation’s leading software partner dedicated solely to the public sector. From financial systems and permitting to utility billing and citizen engagement, Tyler’s solutions help cities and counties operate with efficiency, transparency, and accountability. Their mission is simple: empower public servants to build stronger, smarter, more connected communities.
Learn how Tyler supports local governments at www.tylertech.com
The HaltingWinter Podcast celebrates and elevates the people who power local government. Through in-depth conversations with leaders from cities, counties, and communities of all sizes, host Seth Winterhalter explores the journeys, challenges, and innovations happening in municipal leadership across America.
