Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 290 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
Most people think leadership is about policy, process, and performance.
But anyone who’s spent time in local government knows the truth: leadership eventually becomes personal.
In this episode of The HaltingWinter Podcast, I sit down with Ben Lipps, Town Manager of Cumberland, Indiana, to talk about what happens when the weight of public service moves beyond the job description and into real life.
Ben’s path into leadership didn’t start behind a desk. It started in public works, mowing grass, patching pavement, responding to emergencies, and learning firsthand what it takes to keep a community running. That ground-level experience shaped how he leads today, especially when pressure rises and expectations collide.
And they do collide.
As Cumberland has grown, Ben has navigated zoning conflict, heightened emotions, and a level of incivility that many local government leaders in communities of all sizes in all places are quietly absorbing. In this conversation, he speaks candidly about receiving threats, managing fear without letting it harden him, and staying steady when leadership becomes deeply personal.
This episode isn’t about drama.
It’s about endurance.
It’s about the reality that cities don’t shut off at 5:00 pm, that public trust is fragile, and that leadership often means carrying things no one sees, while still showing up the next day.
If you serve in local government and have ever felt the weight of the seat, this conversation is for you.
🎧 Listen to Episode 290: When Leadership Gets Personal
Because naming the weight is often the first step to carrying it well.
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.
