Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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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?
In Episode 289 of The HaltingWinter Podcast, Seth sits down with Becky Windt Pearson, City Manager of Anchorage, Alaska, to explore what municipal leadership looks like in one of the most demanding environments in North America.
Anchorage isn’t just a city; it’s a hub for healthcare, transportation, emergency response, and essential services for communities across the state. Long supply chains, extreme weather, short construction seasons, and constant pressure redefine what “normal operations” even mean. And yet, the leadership lessons Becky shares reach far beyond Alaska.
This conversation is about:
Becky’s journey—from small-town roots to Harvard and Yale, from law to industry to city management—reinforces a powerful truth: there is no straight line into local government leadership. What matters most is clarity, resilience, and the willingness to carry responsibility when the stakes are real.
Alaska may feel like the edge of the world, but that’s exactly where leadership gets tested, refined, and revealed.
🎧 Listen to Episode 289: Governing at the Edge of the World and reflect on what your community and your leadership can learn from Alaska.
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.
