Municipal Leaders: Develop Faster, Lead Stronger, Build Better

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Episode 397 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

Local government has a hiring problem. Or does it?

Across the country, cities and counties are struggling to fill supervisor, manager, and department-head positions. We talk about shrinking applicant pools, retirements, competition with the private sector, and the difficulty of attracting the next generation into public service.

All legitimate challenges. But what if part of our hiring problem is actually a development problem?

In Episode 397 of The HaltingWinter Podcast, I sit down with Deborah Stuart, City Manager of Mason, Michigan, to talk about what her organization discovered when they started looking more closely at their own people.

After COVID, Deb began conducting “stay” interviews with employees. She wanted to know why they stayed, what they valued about the organization, what frustrated them…and where they wanted to go next.

What she heard exposed a gap. There were talented employees who wanted to grow but didn’t feel prepared for the next opportunity. There were others who had already been promoted and were discovering that being really good at their job hadn’t necessarily prepared them to lead people.

And there’s a glaring problem I don’t think we talk about enough in local government: We keep treating promotion as leadership development when leadership development needs to happen before the promotion.

Your best operator isn’t automatically ready to supervise a crew. Your strongest analyst isn’t automatically prepared to manage a department. Technical competence and leadership competence are not the same thing.

So what would change if we stopped waiting for positions to open before developing the people who might someday fill them?

That’s where Deb and the City of Mason have done some fascinating work. They’ve begun creating clearer pathways for employees who want to grow, finding ways for people to develop leadership experience before they receive the title, and rethinking what an internal leadership pipeline can actually look like.

And the results are worth paying attention to.

Deb knows something about helping others see those possibilities. Her commitment to mentoring and advancing women in municipal leadership has earned her the Christine Burns Award from Michigan Municipal Executives two years in a row.

If you’re looking around your organization wondering where your next generation of leaders is going to come from, this conversation may challenge the question you’re asking.

Your next great leader may already be there. The question is whether you’re developing them before you need them.

Episode 397: Deborah Stuart: Are You Developing Leaders or Just Promoting Employees?

Watch the full conversation on YouTube or listen below.


Tyler Technologies

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 AI to budgeting solutions, Tyler helps local governments build stronger, more resilient communities. Learn more at tylertech.com/winter →

The Municipal Leadership Development Circle (MLDC)

The MLDC Masterminds place local government leaders into small, intentionally curated cohorts with peers who understand the weight and challenges of your unique work. It’s a trusted room to wrestle with specific challenges, gain perspective from leaders across the country, and build the relationships that make you better at what you do. Learn more at haltingwinter.com/mldc →


The HaltingWinter Podcast shines a spotlight on the people behind our cities and counties. Through candid conversations with local government leaders from across the nation, host Seth Winterhalter explores the journeys, challenges, and ideas shaping stronger communities while inspiring the next generation of public servants.