The HaltingWinter Podcast

Jeff Weckbach: The Conversation That Launched a CareerHow Exposure and Mentorship Shape the Next Generation of City Managers

Episode 304 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What if the future of local government hinges on a single conversation?

Before he ever stepped into the Township Administrator's office in Colerain Township, Ohio, Jeff Weckbach was simply a college student completing an assignment. He reached out to then–City Manager Milton Dohoney for an interview.

That hour changed everything.

In this episode, Jeff shares how exposure, not early certainty, set him on the path to municipal leadership. From internships and county government to becoming Township Administrator, his journey highlights something critical: the pipeline doesn't build itself.

Jeff's story is steady, thoughtful, and deeply relevant to today's municipal landscape. It's a reminder that leadership is often shaped long before someone sits in the big chair and that today's leaders have a responsibility to open doors for those coming behind them.

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 – Boundaries for LeadersEpisode 303 of The HaltingWinter Podcast

What if you have more control as a local government leader than you realize? This week in the Municipal Leadership Development Circle, we're exploring "Boundaries for Leaders" by Dr. Henry Cloud, a book that reframes leadership from managing what happens to setting boundaries that create the conditions for success.

In this episode, Seth Winterhalter introduces the core concepts of the book and explains why Cloud's research on neuroscience and leadership is essential for city managers, county administrators, and department heads operating within local government's unique constraints.

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: Boundaries for Leaders by Dr. Henry Cloud

Connect with Seth Winterhalter

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

Travis Coenen: Leading Where Everyone Knows Your NameBuilding Systems That Turn Small-Town Pressures Into Sustainable Growth

Episode 302 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What does leadership look like when everyone in town knows you and isn't afraid to tell you what they think?

In this episode, Seth sits down with Travis Coenen, Village Administrator of Wrightstown, Wisconsin, to explore the weight and reward of leading in a small community. From growing up in a town of 1,200 people to overseeing its expansion to more than 4,000 residents, Travis shares how intentional systems, transparent communication, and long-term stewardship transformed both infrastructure and community trust.

Before becoming an administrator, Travis worked in utility construction, served as a wastewater operator, and was once told he wouldn't even make the interview process for Director of Public Works. He applied anyway.

This conversation is a reminder that local government isn't small work; it's personal, visible, and generational.

If you lead in a community where your reputation lives next door, this episode is for you.

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

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

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

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

Show Notes: MLDC Book of the Week – EssentialismEpisode 300 of The HaltingWinter Podcast

This week inside the Municipal Leadership Development Circle, we're exploring Greg McKeown's "Essentialism: The Disciplined Pursuit of Less," and it will challenge everything you think you know about effective leadership.

In this episode, Seth Winterhalter introduces the core concepts from Essentialism and why they matter specifically for local government leaders. If you're exhausted from trying to do everything, drowning in good opportunities, and spread too thin to make meaningful progress on anything, this book offers a radically different approach.

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: Essentialism: The Disciplined Pursuit of Less by Greg McKeown

Connect with Seth Winterhalter

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

Abbie Ogborn: Leading Before You Feel ReadyGrowth, Grit, and Guiding a Small City Through Big Change

Episode 299 of The HaltingWinter Podcast Brought to you by Tyler Technologies

Abbie Ogborn didn't set out to become a city manager.

She started as a softball umpire in her hometown of Wright City, Missouri. From there, she moved into the parks department, accounts payable, and in February 2020, she was sworn in as the City Clerk.

Three weeks later, City Hall shut its doors.

In this episode, Abbie shares what it was like to step into leadership just before the pandemic and how the crisis accelerated modernization, strengthened regional partnerships, and reshaped how her city serves its residents.

Now serving as both City Manager and City Clerk, Abbie is helping guide Wright City through one of the most significant growth seasons in its history. With nearly 1,900 residential units approved and major infrastructure changes underway, including the expansion of Interstate 70, the pressure to plan well, protect identity, and prepare for the future is right in front of her.

This is a conversation about stepping up when the opportunity arrives, even if you don't feel completely prepared.

It's about learning fast. Listening well. And building a city that can carry its future.

If you lead in local government, especially in a growing community, this episode will feel familiar and encouraging.

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

Craig Honeycutt: Why Compromise Isn't WeaknessThe Emotional Resilience Required to Lead in Local Government

Episode 298 of The HaltingWinter Podcast Brought to you by Tyler Technologies

After more than three decades in municipal leadership, serving as town manager, city manager, county manager, and ultimately retiring as City Manager of Burlington, North Carolina, Craig Honeycutt has learned something many leaders only discover the hard way:

Compromise is not weakness. And criticism is rarely personal.

In this conversation, Craig reflects on a career built from the ground up, starting in small communities, learning operations firsthand, navigating political transitions, leading through natural disasters, and managing in an increasingly polarized climate.

He shares why local government is truly the infrastructure of daily life…why young leaders should start small and "do everything," and why emotional resilience is the defining trait of successful managers today.

This episode is a masterclass in steady leadership, especially in a time when incivility and polarization are testing public servants across the country.

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 – PayoffEpisode 297 of The HaltingWinter Podcast

You can't compete on salary. Your pay scales are rigid. Your bonus structure is practically nonexistent. If motivation really came down to money, you'd be leading the most demoralized teams in America.

Except you're not.

This week inside the Municipal Leadership Development Circle (MLDC), we're exploring "Payoff: The Hidden Logic That Shapes Our Motivations" by Dan Ariely, and what we're discovering is going to change how you think about motivation in your organization.

Dan Ariely is a behavioral economist at Duke University who has spent years running experiments on what actually motivates people. His research proves something revolutionary: we've been completely wrong about motivation. Meaning, acknowledgment, and a sense of accomplishment often work better than money, not just a little better, but dramatically better.

In this episode, you'll discover why your constraints aren't liabilities once you understand what actually drives human motivation, and why the competitive advantage you've been searching for has been hiding in plain sight all along.

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: Payoff: The Hidden Logic That Shapes Our Motivations by Dan Ariely

Connect with Seth Winterhalter

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

Lyndsay Mitchell: From Plans to ProgressBuilding Cities and Preparing the Next Generation of Municipal Leaders

Episode 296 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What happens when great plans never turn into real progress?

In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Lyndsay Mitchell, Director of Strategic Initiatives for the City of Arlington, Texas, for a grounded and candid conversation about what it actually takes to move cities forward and who will be left to do the work if we don't start preparing now.

Lyndsay's journey into local government was anything but linear. She didn't set out to work in city leadership, and like many municipal professionals, she didn't even know these careers existed until late in college. That reality shapes how she thinks today about succession, workforce development, and the growing gap between planning and execution in local government.

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

Jesse Thyes: Built Along the WayHow Leaders Emerge Through Experience

Episode 295 of The HaltingWinter Podcast Brought to you by Tyler Technologies

Most municipal leaders didn't start with a clear plan to achieve their current role. They grew into the role through experience, responsibility, and the people who invited them to step forward.

In this episode, Jesse Thyes, City Administrator of West Bend, Wisconsin, shares his journey from technical roles in planning and zoning to the administrator's chair. Along the way, we explore how early frontline work builds leadership capacity, how mentorship changes trajectories, and why effective municipal leadership is less about status and more about serving the moment.

This conversation is a reminder that leadership isn't assigned early; it's formed over time, through trust, pressure, and the willingness to say yes before you feel ready.

If you've ever questioned your path into leadership or wondered how to develop the next generation, this episode will resonate.

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