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

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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

Connect with Seth Winterhalter

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

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

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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

Connect with Seth Winterhalter

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

Show Notes: MLDC Book of the Week – Inner ExcellenceEpisode 309 of The HaltingWinter Podcast

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This week inside the Municipal Leadership Development Circle, we're exploring "Inner Excellence" by Jim Murphy, a book that went from obscurity to #1 New York Times bestseller overnight when Eagles wide receiver A.J. Brown was caught reading it during an NFL playoff game.

Why did elite performers recognize this book immediately? Because Murphy discovered something revolutionary: the pursuit of extraordinary performance and the pursuit of an exceptional life are the same path.

In this episode, Seth introduces the core insights from "Inner Excellence" and explains why they matter specifically for local government leaders who perform under extreme pressure with limited control.

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: Inner Excellence by Jim Murphy

Connect with Seth Winterhalter

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

Jessica Leavins: Called to CareEmpathy, Public Scrutiny, and the Weight of Municipal Leadership

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Episode 308 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What prepares someone to become a city manager?

For Jessica Leavins, it wasn't a lifelong plan. It was a calling shaped by family roots, social work, organizational psychology, and a deep desire to serve people well.

In this conversation, Jessica shares her journey from growing up in rural Florida on land her family has stewarded for generations, to working in child welfare, to becoming the first HR professional for the City of Crestview, and ultimately stepping into the city manager's seat.

But this episode isn't just about career progression. It's about the emotional reality of municipal leadership.

She speaks candidly about the moment she realized her family could see public criticism online and how that changed her understanding of leadership visibility.

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.

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

Josh Finch: From Manure to ManagementRejection, Resilience, and the Making of a City Administrator

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Episode 307 of The HaltingWinter Podcast Brought to you by Tyler Technologies

There is no "perfect" path into city management. Josh Finch proves it.

From shoveling manure as a seasonal parks laborer to becoming a city administrator at 24, Josh's journey into local government wasn't traditional; it was earned.

In this conversation, Josh shares how a low GPA, rejection from his first administrative interview, and even a life-threatening medical emergency shaped his leadership philosophy. He talks openly about starting in a rural community where he wore every hat — public works, finance, HR, community development — and why that experience became his greatest training ground.

Josh's story is a reminder that no experience is wasted and that leadership isn't about titles, it's about initiative.

His closing advice says it best: "There are people that do, and there are people that don't. Be a doer."

Whether you're an MPA student, an emerging leader, or a seasoned administrator navigating your next chapter, this episode will challenge and encourage you to step forward with humility, resilience, and purpose.

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

Show Notes: MLDC Book of the Week – The One ThingEpisode 306 of The HaltingWinter Podcast

_*]:min-w-0 gap-3">

This week's Municipal Leadership Development Circle Book of the Week is "The One Thing" by Gary Keller and Jay Papasan, and it has some unique insights that we'll be translating for effective leadership in local government.

How many priorities are you juggling right now? Council demands, staff needs, community expectations, budget pressures, organizational initiatives? If you're like most municipal leaders, you stopped counting around twelve.

But what if the reason you're not getting the results you want isn't because you're not working hard enough; it's because you're working on too many things?

In this episode, Seth Winterhalter introduces the powerful framework from "The One Thing" and explains why it's perfectly suited for the impossible demands local government leaders face daily. You'll discover why extraordinary results come from radical focus, not multitasking, and how identifying your ONE Thing creates a domino effect that makes everything else easier.

This is just a preview. Inside the MLDC this week, members are getting daily insights, practical implementation strategies, and conversation guides specifically designed for the unique constraints of municipal leadership.

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: The One Thing by Gary Keller

Connect with Seth Winterhalter

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

Ken Striplin: Culture Is Built, Not AssumedWhat It Takes to Develop Leaders and Sustain Excellence in Local Government

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Episode 305 of The HaltingWinter Podcast Brought to you by Tyler Technologies

What does it actually take to build a municipal culture that lasts?

Not slogans. Not one-off trainings. Not a new strategic plan every few years.

In this episode, Ken Striplin, City Manager of Santa Clarita, California, shares what 30 years inside one organization has taught him about leadership, development, and intentional culture-building.

From starting as an intern to leading a city that has doubled in population under his tenure, Ken offers a rare inside look at how sustainable excellence is created and measured.

We explore:

• Why leadership is transferable and technical skills are learnable

• The power of saying "yes" before you feel fully ready

• How structured mentorship changes identity, not just performance

• Why culture must be programmed, measured, and reinforced

• The role of job shadowing and cross-department exposure in breaking silos

Santa Clarita doesn't guess about engagement. They measure it.

With 91% employee survey participation and scores that reflect genuine pride in the workplace, Ken shares the systems behind the success: leadership academies, mentoring cohorts, wellness initiatives, and intentional succession planning.

If you care about building a culture that outlives your tenure… If you're developing the next generation of municipal leaders… If you're wrestling with growth, burnout, or the weight of the city manager role…

This episode will challenge and encourage you. Because culture isn't accidental.

It's built. And it's worth building well.

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

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

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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

Connect with Seth Winterhalter

• 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

_*]:min-w-0 gap-3">

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

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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

Connect with Seth Winterhalter

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