Municipal Leaders: Develop Faster, Lead Stronger, Build Better

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Episode 307 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

What does shoveling horse stalls have to do with becoming a city administrator?

More than you’d think.

In Episode 307 of The HaltingWinter Podcast, Josh Finch shares his unlikely path into local government, from seasonal parks laborer to City Administrator in Waupaca, Wisconsin.

His journey wasn’t polished. It wasn’t linear. And it certainly wasn’t guaranteed.

Josh talks candidly about:

  • Being told college might not be for him
  • Getting rejected from the very job he would later be hired for
  • Managing COVID logistics early in his career
  • Surviving a life-threatening health crisis that reshaped his priorities
  • Why starting in a rural community forced him to learn every side of municipal leadership

At just 24 years old, Josh stepped into his first administrator role in a small Wisconsin community where he wore every hat — public works, finance, HR, community development — because if he didn’t do it, no one else would.

His story is a powerful reminder that leadership is built in the small places, in the hard seasons, and in the moments when you choose to keep showing up.

He leaves us with a simple but challenging truth: There are people that do. And there are people that don’t. Be a doer.

If you’re an emerging leader, a rural administrator, or someone wondering whether your path “counts,” this episode will remind you that no experience is wasted.

Listen to Episode 307 here:

Tyler Technologies

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 Municipal Leadership Development Circle (MLDC)

The MLDC is where local government leaders go to grow, together. It’s the fastest-growing leadership development community designed specifically for the public sector, now paired with a comprehensive 9-month Leadership & Culture Program for those ready to elevate their leadership and their organization.
Learn more at haltingwinter.com/mldc →

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.