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

• 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

• LinkedIn: www.linkedin.com/in/sethwinterhalter
• Website: www.HaltingWinter.com