Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 266 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
Most people spend their careers trying to avoid storms.
City managers don’t get that luxury.
In this week’s episode of The HaltingWinter Podcast, I talk with Rebecca Grill, City Manager of Oshkosh, Wisconsin, a leader whose entire career has been shaped by one defining principle:
When the storm forms, don’t wait for it to pass. Run toward it.
Rebecca’s path into city management wasn’t linear. She began in youth corrections, where she learned the hard truth that compassion without boundaries burns leaders out. She modernized licensing systems in Milwaukee, led through intense public pressure, and stepped into a city administrator role after a 33-year predecessor—walking straight into cultural change, budget constraints, and the expectations of an entire community.
Today, in Oshkosh, she’s pushing technology forward, breaking old silos, strengthening customer experience, and challenging her team to improve the organization without losing sight of the people who depend on it.
This conversation is honest, grounded, and deeply relevant.
It’s about courage.
It’s about clarity.
It’s about the leaders who choose to run toward the storm so their communities don’t have to.
If you’re in local government— and especially if you carry the weight of leadership—this episode will remind you why the work matters and what it demands.
Listen here: 266: Rebecca Grill: Running Toward the Storm
Available now on Apple Podcasts, Spotify, and all podcast platforms or at HaltingWinter.com/resources.
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 organization.
Members receive weekly leadership content, access to our daily podcast, monthly virtual trainings, and a clear roadmap for building a culture that reduces burnout, strengthens retention, and drives meaningful impact in every department.
If you’re committed to leading well and shaping a healthier culture for your team, now is the time to save your seat for the 2026 cohort.
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.
