The HaltingWinter Podcast

Deborah Stuart: Are You Developing Leaders or Just Promoting Employees?
Rethinking the Leadership Pipeline in Local Government

Episode 397 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

What if the biggest challenge in your leadership pipeline isn't finding better people but preparing the people you already have?
In Episode 397 of The HaltingWinter Podcast, Seth Winterhalter sits down with Deborah Stuart, City Manager of Mason, Michigan, to explore what it takes to intentionally develop the next generation of municipal leaders.
Deborah shares how "stay" interviews helped her uncover what employees actually wanted from their careers and where the organization was unintentionally setting talented people up for failure. Being technically excellent at a job doesn't automatically prepare someone to manage people, navigate conflict, oversee budgets, or lead a team.
That realization led Mason to rethink its approach to employee development, creating clearer pathways for advancement and giving employees opportunities to build leadership skills before the next position opens.
Seth and Deborah also discuss why people sometimes need someone else to help them see what's possible, the importance of mentorship in city management, and why economic development is ultimately about relationships, not simply incentives, projects, and data.
Deb's commitment to developing and supporting others has also earned her the Christine Burns Award from Michigan Municipal Executives two years in a row, recognizing her work to support and advance women in the municipal management profession.
About Deborah Stuart
Deborah Stuart serves as City Manager for the City of Mason, Michigan, a role she has held since 2016. Her career includes extensive experience in downtown and economic development at both the local and state levels before moving into city management. She is passionate about developing people from within, creating visible pathways for employee growth, and helping emerging leaders recognize opportunities they may not yet see for themselves.
This Episode is Sponsored by:
Tyler Technologies – the nation's leading provider of software and technology solutions built specifically for local government. From artificial intelligence and resident engagement to budgeting, planning, and public service delivery, Tyler helps communities operate more efficiently and serve residents more effectively. Learn more at https://tylertech.com/winter
The Municipal Leadership Development Circle (MLDC): Leadership shouldn't be carried alone. The MLDC is evolving in 2027 with practical leadership development and new, role-specific Mastermind cohorts designed to build trusted relationships with municipal leaders who understand your challenges. Mastermind applications are open now: https://haltingwinter.com/MLDC
Connect With Seth Winterhalter
Seth Winterhalter is a keynote speaker, storyteller, and President of HaltingWinter, a national media company dedicated to telling the stories of local government. Through The HaltingWinter Podcast and the nationwide HaltingWinter Tour, he highlights the people and communities shaping America from the ground up, celebrating public servants, strengthening the profession, and inspiring the next generation to pursue lives of purpose and impact through local government.
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com

Show Notes: MLDC Book of the Week: The Motive
Episode 396 of The HaltingWinter Podcast
This week in the MLDC, Seth Winterhalter explores The Motive by Patrick Lencioni, a leadership fable built around two rival CEOs, one struggling and one quietly thriving, and the uncomfortable conversation that reveals why. Lencioni draws a sharp distinction between leaders who take the top job as a reward for hard work, and leaders who take it as a responsibility to do the difficult, unglamorous work their organization actually needs.
Seth breaks down why this question hits differently for local government leaders than it does in the private sector, as many city managers, county administrators, and department heads didn't arrive in leadership through pure ambition, but through tenure, reliability, or simply being next in line. That path makes it easy to never stop and ask which motive is actually driving you.
Inside MLDC this week, members are working through five specific takeaways from the book and applying them to their local government context.
The MLDC
Leadership in local government doesn't get easier as you move up. The decisions get harder. The expectations get higher. And the number of people you can openly process those challenges with gets smaller.
The Municipal Leadership Development Circle (MLDC) gives local government leaders a place to keep growing alongside other professionals who understand the complexity of leading in local government.
Inside the MLDC, you'll sharpen how you think, strengthen how you lead, and turn leadership ideas into practical action through:
• Monthly Mastermind Sessions with municipal leaders from across North America
• Leadership Development built specifically around the realities of local government
• Practical Tools & Resources you can immediately apply with your team and organization
• Ongoing Learning designed to keep you growing throughout the year
You spend every day developing your organization, your employees, and your community.
The MLDC is an investment in developing you.
→ Explore the Municipal Leadership Development Circle: https://haltingwinter.com/mldc/
Connect With Seth Winterhalter
Seth Winterhalter is a keynote speaker and President of HaltingWinter, a national media company dedicated to telling the stories of local government. Through The HaltingWinter Podcast and the nationwide HaltingWinter Tour, he highlights the people and communities shaping America from the ground up, celebrating public servants, strengthening the profession, and inspiring the next generation to pursue lives of purpose and impact through local government.
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com

Jennifer Miller: "No" Is the Lazy Answer
Breaking Silos and Building a Culture That Solves Problems

Episode 396 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

"No" is often the easiest answer in government. It gets the issue off your desk, protects the process, and keeps things moving. But as Jennifer Miller, Deputy County Executive for Fairfax County, Virginia, puts it: "No is the lazy answer." Great leadership requires something harder: helping people understand what is possible, breaking through organizational silos, and creating a culture where people are empowered to solve problems.
In this episode, Jennifer joins Seth to explore what she learned through more than two decades of military and federal service and how those lessons translate into local government leadership. They discuss why residents don't care whose department owns the problem, how cross-functional teams can become powerful "silo busters," why leaders must protect employees who take creative risks, and the responsibility professional staff have to enable informed decision-making. It's a conversation about moving beyond bureaucracy as an excuse and building organizations designed to collaborate, innovate, and get things done.
About Jennifer Miller
Jennifer Miller is the Deputy County Executive for Fairfax County, Virginia, where she helps lead one of the largest local governments in the country. Before joining Fairfax County, Jennifer spent more than two decades serving in senior civilian leadership roles with the Department of the Air Force while also serving in the U.S. Army Reserve. Her career has spanned law, real estate, infrastructure, environmental policy, military service, and executive leadership, giving her a unique perspective on leading complex, mission-driven organizations.
Jennifer will also be presenting the education session "Mission Driven Leadership: Veterans Building Trust and Integrity in Local Government" on Sunday, October 18th. The session will explore how military experience translates into local government leadership, how communities can better recognize the skills veterans bring, and how veterans can translate their experience for careers in cities and counties.
This Episode is Sponsored by:
Tyler Technologies – the nation's leading provider of software and technology solutions built specifically for local government. From artificial intelligence and resident engagement to budgeting, planning, and public service delivery, Tyler helps communities operate more efficiently and serve residents more effectively. Learn more at https://tylertech.com/winter
The Municipal Leadership Development Circle (MLDC): Leadership shouldn't be carried alone. The MLDC is evolving in 2027 with practical leadership development and new, role-specific Mastermind cohorts designed to build trusted relationships with municipal leaders who understand your challenges. Mastermind applications are open through October 31st at https://haltingwinter.com/MLDC
Connect With Seth Winterhalter
Seth Winterhalter is a keynote speaker, storyteller, and President of HaltingWinter, a national media company dedicated to telling the stories of local government. Through The HaltingWinter Podcast and the nationwide HaltingWinter Tour, he highlights the people and communities shaping America from the ground up, celebrating public servants, strengthening the profession, and inspiring the next generation to pursue lives of purpose and impact through local government.
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com

Melissa Marsh: Being Capable Doesn't Mean Carrying It All
How to Step Up, Speak Up, and Protect Your Capacity

Episode 394 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

The people who rise in local government are often the ones willing to step up, take on more, and solve problems no one asked them to solve. But what happens when everyone gets so used to you carrying more that they stop noticing how much you're carrying? Melissa Marsh, City Manager of Madison Heights, Michigan, shares how her willingness to raise her hand opened doors throughout her career and why she eventually had to learn to advocate for her own value and protect her capacity.
Melissa and Seth also talk about why high performers can become invisible, making decisions without getting trapped in bureaucracy, taking ownership of your professional development, and setting boundaries at the city manager level. Melissa also shares the story behind Madison Heights' Business Bus Tour and how getting city leaders out of City Hall and into local businesses helped build stronger relationships and trust throughout the community.
About Melissa Marsh
Melissa Marsh is the City Manager of Madison Heights, Michigan. Beginning her local government career in finance, Melissa steadily expanded her leadership responsibilities across human resources, information technology, library services, and administration before becoming City Manager. Her career reflects a willingness to step up, keep learning, and take on new challenges while building a more connected and responsive organization
If you're attending the ICMA Annual Conference in Long Beach, you can also hear Melissa during the education session "The Road to Trust: How a Business Bus Tour Built Collaboration and Community" on Monday, October 19th.
This Episode is Sponsored by:
Tyler Technologies – the nation's leading provider of software and technology solutions built specifically for local government. From artificial intelligence and resident engagement to budgeting, planning, and public service delivery, Tyler helps communities operate more efficiently and serve residents more effectively. Learn more at https://tylertech.com/winter
The Municipal Leadership Development Circle (MLDC): Leadership shouldn't be carried alone. The MLDC is evolving in 2027 with practical leadership development and new, role-specific Mastermind cohorts designed to build trusted relationships with municipal leaders who understand your challenges. Mastermind applications are open through October 31st at https://haltingwinter.com/MLDC
Connect With Seth Winterhalter
Seth Winterhalter is a keynote speaker, storyteller, and President of HaltingWinter, a national media company dedicated to telling the stories of local government. Through The HaltingWinter Podcast and the nationwide HaltingWinter Tour, he highlights the people and communities shaping America from the ground up, celebrating public servants, strengthening the profession, and inspiring the next generation to pursue lives of purpose and impact through local government.
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com

Show Notes: MLDC Book of the Week: The Anatomy of Peace
Episode 393 of The HaltingWinter Podcast
This week's book centers on an unlikely pairing: Yusuf, a Palestinian, and Avi, an Israeli, each of whom lost his father to the other side's conflict. Rather than let that history define them, they built a program together for resolving conflicts that seem permanent: the kind where both sides are certain, with real evidence, that they're the reasonable one.
That's the premise behind The Anatomy of Peace, by the Arbinger Institute, and it's a book every local government leader should sit with. The core claim is uncomfortable but hard to argue with: most of the conflicts we think are being caused by the other person are actually being sustained by how we've already decided to see them. Council dynamics, staff conflict, community pushback...these patterns show up everywhere municipal leadership actually happens.
In this episode, Seth Winterhalter gets into why this book landed differently than most leadership reading we've worked through in the MLDC, what the "heart at war vs. heart at peace" distinction actually means in practice, and why the fix isn't a better tactic — it's a different way of seeing the person in front of you. If you've got a relationship at work that's stuck and you can't quite tell whose fault it is, this one's worth your five minutes.
The MLDC
Leadership in local government doesn't get easier as you move up. The decisions get harder. The expectations get higher. And the number of people you can openly process those challenges with gets smaller.
The Municipal Leadership Development Circle (MLDC) gives local government leaders a place to keep growing alongside other professionals who understand the complexity of leading in local government.
Inside the MLDC, you'll sharpen how you think, strengthen how you lead, and turn leadership ideas into practical action through:
• Monthly Mastermind Sessions with municipal leaders from across North America
• Leadership Development built specifically around the realities of local government
• Practical Tools & Resources you can immediately apply with your team and organization
• Ongoing Learning designed to keep you growing throughout the year
You spend every day developing your organization, your employees, and your community.
The MLDC is an investment in developing you.
→ Explore the Municipal Leadership Development Circle: https://haltingwinter.com/mldc/
Connect With Seth Winterhalter
Seth Winterhalter is a keynote speaker and President of HaltingWinter, a national media company dedicated to telling the stories of local government. Through The HaltingWinter Podcast and the nationwide HaltingWinter Tour, he highlights the people and communities shaping America from the ground up, celebrating public servants, strengthening the profession, and inspiring the next generation to pursue lives of purpose and impact through local government.
LinkedIn: https://www.linkedin.com/in/sethwinterhalter
Website: https://www.HaltingWinter.com