The HaltingWinter Podcast

Ben Lipps: When Leadership Gets Personal
Incivility, Threats, and Staying Steady in Local Government
Episode 290 of The HaltingWinter Podcast Brought to you by Tyler Technologies
What happens when leadership stops being theoretical and starts showing up at your door?
In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Ben Lipps, Town Manager of Cumberland, Indiana, to explore what it means to lead when public service becomes personal.
Ben's journey into local government didn't begin in city hall; it began on the front lines of public works. From mowing grass and fixing potholes to supervising infrastructure, managing emergencies, and ultimately stepping into the town manager's seat, Ben's story is one of earned credibility, steady growth, and leadership forged through experience rather than title.
But this conversation goes deeper.
Ben shares candidly about navigating community growth, zoning conflict, and the rising incivility many local government leaders now face, including personal threats that tested not just his role, but his resilience. Together, Seth and Ben unpack the emotional weight of the manager's chair, the hidden cost of public outrage, and what it takes to stay grounded when leadership stops at 5:00 pm for no one.
Sponsored by:
Tyler Technologies – the nation's leading provider of software solutions designed specifically for the public sector and local government. Learn more at https://tylertech.com/winter

The Municipal Leadership Development Circle (MLDC) is a global community for local government leaders who want ongoing support, practical insights, and a trusted peer network to help them lead with clarity and conviction. Learn more at https://haltingwinter.com/MLDC
Connect with Seth Winterhalter
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com

Becky Windt Pearson: Governing at the Edge of the World
What Alaska Teaches Us About Leadership, Resilience, and Responsibility
Episode 289 of The HaltingWinter Podcast Brought to you by Tyler Technologies
What does leadership look like when your city is the end of the road...literally?
In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Becky Windt Pearson, City Manager of Anchorage, Alaska, to explore what municipal leadership looks like in one of the most demanding contexts in North America.
Anchorage isn't just Alaska's largest city; it's a hub for healthcare, transportation, emergency response, and essential services for communities across the state. That reality creates pressures, responsibilities, and leadership challenges that most cities never face. And yet, the lessons Becky shares extend far beyond Alaska.
This conversation is about clarity under pressure, leadership without illusion, and the responsibility local government carries when no one else can step in.
Sponsored by:
Tyler Technologies – the nation's leading provider of software solutions designed specifically for the public sector and local government. Learn more at https://tylertech.com/winter

The Municipal Leadership Development Circle (MLDC) is a global community for local government leaders who want ongoing support, practical insights, and a trusted peer network to help them lead with clarity and conviction. Learn more at https://haltingwinter.com/MLDC
Connect with Seth Winterhalter
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com

Show Notes: MLDC Book of the Week – The Burnout Epidemic
Episode 288 of The HaltingWinter Podcast
Your wellness program isn't fixing burnout, and Jennifer Moss explains why. This week's MLDC book, "The Burnout Epidemic," reveals that burnout isn't a personal problem requiring more yoga and meditation apps. It's an organizational design flaw that local government leaders have the power to fix.
In this episode, Seth introduces the six root causes of burnout and why each one shows up uniquely in municipal and county government. Moss wrote this book during the pandemic while experiencing burnout herself, and her insights hit differently for leaders still navigating hybrid work, staffing shortages, and exhausted teams. This isn't another self-care prescription. It's a framework for diagnosing what's actually broken in your organization and taking specific steps to fix it.
Join the Municipal Leadership Development Circle (MLDC) to explore this book in depth with daily insights, practical applications, and a community of peers facing the same challenges. Learn more at HaltingWinter.com/MLDC.
Join the MLDC for the Complete 5-Part Series
The Municipal Leadership Development Circle (MLDC) is a network of local government leaders from across North America, including city/county managers, administrators, and department heads, giving you access to: 

     ✔ A weekly podcast series breaking down one book for municipal applications
     ✔ Daily blog reflections and implementation tools
     ✔ Our live, weekly, virtual mastermind session
     ✔ Monthly webinars with relevant training from local gov leaders
➡ Learn more at www.HaltingWinter.com/MLDC
Resources Mentioned
Book: The Burnout Epidemic by Jennifer Moss
Connect with Seth Winterhalter
LinkedIn: www.linkedin.com/in/sethwinterhalter
Website: www.HaltingWinter.com

Jennifer Bromeland: When Small Cities Carry Big Expectations
Collaboration, Communication, and Community Trust
Episode 287 of The HaltingWinter Podcast Brought to you by Tyler Technologies
In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Jennifer Bromeland, City Administrator of Eagle Lake, Minnesota, to explore what leadership really looks like in small cities: where expectations are high, resources are limited, and relationships matter more than titles.
Jennifer shares her journey into local government, the realities of leading in small and rural communities, and why collaboration across sectors isn't a "nice-to-have," but essential to community success. From working closely with school districts to address childcare shortages to navigating growth, identity, and trust in a bedroom community, this conversation highlights the unseen work that keeps cities moving forward.
This episode is a powerful reminder that small cities don't have small problems and that effective municipal leadership is built on communication, adaptability, and trust.
Sponsored by:
Tyler Technologies – the nation's leading provider of software solutions designed specifically for the public sector and local government. Learn more at tylertech.com/winter

The Municipal Leadership Development Circle (MLDC) is a global community for local government leaders who want ongoing support, practical insights, and a trusted peer network to help them lead with clarity and conviction. Learn more at haltingwinter.com/MLDC
Connect with Seth Winterhalter
LinkedIn: www.linkedin.com/in/sethwinterhalter
Website: www.HaltingWinter.com

Dennis Champine: Built for the Long Haul
How One City Manager Outlasted Politics, Turnover, and Trend-Driven Leadership
Episode 286 of The HaltingWinter Podcast Brought to you by Tyler Technologies
What does it take to last in local government when the average city manager tenure is shrinking and the pressure keeps rising?
In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Dennis Champine, City Manager of Center Line, Michigan, recently named one of the Top 10 City Managers of 2025. Dennis has served his community for more than a decade, not by chasing headlines or political wins, but by playing the long game.
Dennis' story is anything but traditional. From growing up in a low-income household, to serving in the Marine Corps, to entering formal higher education at age 40, his path into city management was shaped by service, setbacks, and lived experience, not ambition for the title.
In this conversation, Dennis shares what he's learned about endurance in a role designed to wear people down, including:
Why longevity in city management comes from listening more than persuading

How he reduced one of the highest tax rates in his county without cutting services

The power of regional and federal partnerships to create new revenue without burdening residents

What it really means to remain professionally neutral in an increasingly polarized environment

How to engage residents when few show up to meetings, but everyone has an opinion

Why integrity, restraint, and humility matter more than being right or popular

This episode is for city managers, administrators, and senior leaders who are tired of trend-driven leadership and short-term thinking and who want to build something that lasts.
If you've ever wondered how to stay grounded, effective, and human in the middle of political pressure and public scrutiny, this conversation is for you.
Sponsored by:
Tyler Technologies – the nation's leading provider of software solutions designed specifically for the public sector and local government. Learn more at tylertech.com/winter

The Municipal Leadership Development Circle (MLDC) is a global community for local government leaders who want ongoing support, practical insights, and a trusted peer network to help them lead with clarity and conviction. Learn more at haltingwinter.com/MLDC
Connect with Seth Winterhalter
LinkedIn: www.linkedin.com/in/sethwinterhalter
Website: www.HaltingWinter.com