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

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

• LinkedIn: https://www.linkedin.com/in/sethwinterhalter
• Website: https://www.HaltingWinter.com

Jennifer Callaway: Leading What You Don't Know
Why Great Leaders Trust People More Than Their Own Expertise

Episode 316 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Most leaders feel the pressure to have the answers. To be the expert. To walk into every room with clarity, confidence, and control.

But what if that's not what great leadership actually requires?

In this conversation, Seth Winterhalter sits down with Jennifer Callaway, Town Manager of Truckee, California, who shares a different path, one shaped not by expertise but by trust. Trust in her team. Trust in the process. And trust in the idea that leadership isn't about knowing everything…it's about creating the conditions for others to thrive.

From starting her career with no clear awareness of local government, to leading complex challenges around housing, tourism, and community identity, Jennifer offers a grounded and honest look at what it really takes to lead in today's environment.

This episode explores the shift from doer to leader, the discipline of listening to understand, and why some of the most impactful decisions aren't driven by technical knowledge, but by people.

If you've ever felt the weight of needing to have it all figured out…this conversation will challenge that assumption and offer a better way forward.

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

• LinkedIn: https://www.linkedin.com/in/sethwinterhalter
• Website: https://www.HaltingWinter.com

Show Notes: MLDC Book of the Week – Leading With Questions
Episode 315 of The HaltingWinter Podcast

Most local government leaders were promoted because they had the best answers. But what if that instinct—the automatic move toward the answer—is quietly limiting the people around you?

In this episode, Seth Winterhalter introduces the MLDC book of the week: Leading with Questions by Michael J. Marquardt. It's a book about one of the most common and most costly habits in leadership, and why the shift from answer-giving to question-asking may be the highest-leverage move available to local government leaders today.

If you want to go deeper, the MLDC is exploring the insights from this book all week through daily blog posts, podcast episodes, and implementation tools built specifically for city and county leaders. Learn more at HaltingWinter.com/MLDC.

Join the MLDC for the Complete 5-Part Series

The Municipal Leadership Development Circle (MLDC) is a network of local government leaders from across North America, including city/county managers, administrators, and department heads, giving you access to:

✔ A weekly podcast series breaking down one book for municipal applications
✔ Daily blog reflections and implementation tools
✔ Our live, weekly, virtual mastermind session
✔ Monthly webinars with relevant training from local gov leaders

➡ Learn more at www.HaltingWinter.com/MLDC

Resources Mentioned

• Book: Leading With Questions by Michael J. Marquardt

Connect with Seth Winterhalter

• LinkedIn: www.linkedin.com/in/sethwinterhalter
• Website: www.HaltingWinter.com

Peter Pirnejad: Leading Before You're Ready
The Hidden Crisis Facing the Next Generation of City Managers

Episode 314 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Local government leadership has changed. Not gradually. Not subtly. But quickly and in ways most leaders weren't prepared for.

In this episode, Seth Winterhalter sits down with Dr. Peter Pirnejad, former city manager and now Executive Director of the Davenport Institute, to unpack what's really happening inside today's cities and counties.

Leaders are stepping into roles earlier than ever before. The expectations are higher. The pressure is heavier. And the environment they're walking into is marked by distrust, disruption, and constant change.

The result?

Many are being asked to lead before they've had the time—or training—to truly be ready. But this isn't a conversation about failure. It's a conversation about reality.

Peter shares insights from nearly three decades in local government, the private sector, and academia to help leaders understand:

• Why the traditional path to leadership is disappearing
• How the role of the city manager has shifted from operational to deeply relational
• What it actually takes to build trust in today's climate
• And why the future of local government depends on developing leaders differently

Because while the work has changed…the mission hasn't.

If you're serving in local government or preparing to step into greater responsibility, this is a conversation that will help you lead with greater clarity, awareness, and intention.

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

• LinkedIn: https://www.linkedin.com/in/sethwinterhalter
• Website: https://www.HaltingWinter.com

Chris Fabian: The Story Your Budget Is Telling
How Leaders Align Resources, Priorities, and Outcomes to Drive Impact

Episode 313 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Local government leaders don't struggle because they lack resources. They struggle because they lack clarity on where those resources are actually going and whether they're aligned with what matters most.

In this episode, Seth sits down with Chris Fabian, Senior Director of Product Strategy at Tyler Technologies and co-creator of Priority-Based Budgeting, to unpack one of the most overlooked leadership challenges in local government: the gap between what we say we value and what we actually fund.

From his early days in civil engineering to helping cities and counties across the country rethink how they allocate millions of dollars, Chris shares how budgeting isn't just a financial exercise; it's a reflection of your organization's priorities, strategy, and impact.

This conversation challenges leaders to move beyond line items and legacy processes and instead ask a better question: What story is your budget telling?

And more importantly…is it the story you want your community to experience?

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

• LinkedIn: https://www.linkedin.com/in/sethwinterhalter
• Website: https://www.HaltingWinter.com

Show Notes: MLDC Book of the Week – Turn the Ship Around
Episode 312 of The HaltingWinter Podcast

Most local government organizations are built on a model that quietly undermines the people inside them. One person at the top makes the calls. Everyone else executes. Information travels up. Decisions travel down. And your most capable people (the ones with the most context, the most experience, the most judgment) learn to wait for permission.

This week's MLDC book of the week is "Turn the Ship Around" by L. David Marquet, and it's one of the most direct challenges to that model you'll find anywhere. Marquet commanded the USS Santa Fe, a nuclear submarine with the worst performance record in the U.S. Navy fleet, and turned it into the best by fundamentally changing where authority lived in the organization.

In this episode, Seth Winterhalter introduces the book, unpacks why it lands differently for local government leaders than most leadership reads, and gives you a taste of what we're covering in depth inside the Municipal Leadership Development Circle (MLDC) this week.

Join the MLDC for the Complete 5-Part Series

The Municipal Leadership Development Circle (MLDC) is a network of local government leaders from across North America, including city/county managers, administrators, and department heads, giving you access to:

✔ A weekly podcast series breaking down one book for municipal applications
✔ Daily blog reflections and implementation tools
✔ Our live, virtual mastermind sessions
✔ Monthly webinars with relevant training from local gov leaders

➡ Learn more at www.HaltingWinter.com/MLDC

Resources Mentioned

• Book: Turn the Ship Around by L. David Marquet

Connect with Seth Winterhalter

• LinkedIn: www.linkedin.com/in/sethwinterhalter
• Website: www.HaltingWinter.com

Jerry Gabrielatos: Artificial Intelligence and the Stewardship of Time
Reclaiming Capacity to Better Serve Your Community

Episode 311 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Artificial Intelligence is no longer a future conversation; it's here. And for local government leaders, the real question isn't whether to use it…it's what you do with the time it gives back.

In this episode, Seth sits down with returning guest Jerry Gabrielatos (former City Manager of Beloit, WI) to unpack a powerful idea: AI should lead to more humanity, not less.

Drawing from his recent article on AI and local government, Jerry challenges leaders to rethink how they spend their time, how they engage their communities, and how they structure their organizations in a rapidly changing landscape.

This isn't a technical conversation; it's a leadership one.

Throughout the conversation, one theme stands out: Municipal leadership isn't about applause. It's about doing good with good people, even when it's heavy.

Read Jerry's Article
Listen to Jerry's First Interview (Episode 111)

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

• LinkedIn: https://www.linkedin.com/in/sethwinterhalter
• Website: https://www.HaltingWinter.com

Benjamin Bitter: Impact Over Title
Why Great City Managers Focus on People, Not Position

Episode 310 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

What does it really mean to lead in local government?

For Benjamin Bitter, City Manager of Maricopa, Arizona, the answer is simple, but not easy: It's not about the title. It's about the impact.

In this conversation, Benjamin shares a leadership philosophy shaped not by ambition, but by service, where success isn't measured by position or power, but by the ability to improve people's lives every single day.

From navigating rapid city growth to leading through uncertainty, Benjamin offers a grounded and refreshing perspective on what it takes to lead well in today's municipal environment.

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

• LinkedIn: https://www.linkedin.com/in/sethwinterhalter
• Website: https://www.HaltingWinter.com