Monica Dupee: Kindness Over NicenessWhy Avoiding Hard Conversations Is Quietly Breaking Your Culture

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Episode 317 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What if the biggest threat to your culture isn't conflict…but your desire to avoid it?

In this conversation, Seth Winterhalter chats with Monica Dupee, City Manager in Westerville, Ohio, who shares a candid look at the leadership lessons shaped through her journey, from small-town beginnings to leading complex municipal organizations through recession, political tension, and a global pandemic.

At the center of it all is a simple but powerful distinction: niceness and kindness are not the same.

Too often, leaders choose to be nice—avoiding hard conversations, softening expectations, and letting issues linger. But over time, that avoidance creates confusion, erodes trust, and quietly fractures culture.

Monica challenges that instinct and offers a better path—one rooted in clarity, accountability, and genuine care for people. Because real leadership isn't about keeping everyone comfortable. It's about telling the truth in a way that helps people grow.

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