Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 295 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
Most municipal leaders don’t wake up one day knowing they’re ready to lead.
They grow into it through technical roles, unexpected opportunities, hard conversations, and mentors who see something in them before they see it in themselves.
In this episode of The HaltingWinter Podcast, I sit down with Jesse Thyes, City Administrator of West Bend, Wisconsin, to talk about a leadership path shaped not by early certainty, but by experience. Jesse shares how frontline work in planning and zoning quietly prepared him for executive leadership, why mentorship matters only when someone is willing to ask, and how the most effective municipal leaders understand leadership as service, not status.
This is a conversation for anyone who didn’t plan to lead but found themselves called forward anyway and for those wondering how we prepare the next generation of municipal leaders to do the same.
Listen to Episode 295: Built Along the Way
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 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.
