290: Ben Lipps: When Leadership Gets Personal
Thu Feb 05 2026
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
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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