Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 257 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
Most leadership stories highlight the victories: the growth, the vision, the change.
Matt Stiles’ story starts in the struggle.
He grew up in poverty, raised by a mother fighting severe mental illness, in a town where every day was about survival. He wasn’t supposed to lead cities. But that’s exactly what makes his story so powerful, because it’s grounded in the realities that most leaders quietly carry.
Matt climbed his way into city management, serving communities across Kansas. But years later, after political conflict and burnout in his hometown of South Hutchinson, he faced the hardest leadership decision there is: to step away. Not because he stopped caring, but because he cared too much to keep breaking himself in the process.
That decision—leaving—became his turning point.
After a season of teaching and consulting, he rediscovered his purpose. When the pandemic hit, Hillsboro, Kansas called. Matt said yes—not from ambition, but from alignment.
Now, years later, he’s helping rebuild trust, culture, and leadership in a small-town city hall. His story is a reminder to every city and county manager, every department head, and every public servant:
Sometimes the bravest thing you can do is pause.
And sometimes grace gives you just enough space to find the grit to begin again.
Episode 257: “The Grace to Leave and the Grit to Return”
Available on Apple Podcasts, Spotify, and at haltingwinter.com/resources
This episode is sponsored by Tyler Technologies, the leader in empowering the public sector with software solutions that connect data, streamline operations, and improve service delivery. From civic services to public safety, Tyler helps local governments build stronger, more resilient communities.
Learn more at tylertech.com/winter →
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.
