Brian Heck: Thick Skin, Soft HeartAbsorbing Criticism While Building Communities That Last

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Episode 301 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What does it take to lead in local government for nearly four decades?

In this episode, Seth sits down with Brian Heck, City Administrator of Montgomery, Minnesota, who was recently named one of the Top 10 City Administrators for 2026. After 38 years serving in city, county, and state government, and now preparing for retirement, Brian reflects on the realities few people see behind the title.

He shares candidly about being fired twice, learning resilience the hard way, and discovering that city managers are "all interim…it just depends on how long."

From rebuilding infrastructure and restructuring failing utility finances to revitalizing a historic downtown, Brian walks through the long-game work of municipal leadership: work that rarely makes headlines but shapes communities for generations.

He also speaks honestly about the personal cost of constant availability, the lesson of putting the oxygen mask on yourself first, and why thick skin must be paired with a soft heart.

Leadership in a small city isn't glamorous. It isn't always secure. It won't make you wealthy.

But it can make you impactful.

And if you do it well, you leave your community stronger than you found it.

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