The HaltingWinter Podcast

Kimberly Richardson: The Hidden Power of Strategic Planning
How a shared vision can transform leadership, collaboration, and organizational culture.
Episode 409 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

America Runs on Local Government. Now you can wear the message with pride and help us tell the stories behind it. Shop the limited-edition Founders Collection, available for preorder through November 22: https://shop.haltingwinter.com/
What if your city's strategic plan could do more than establish priorities? What if it could actually transform your organizational culture?
In this episode of The HaltingWinter Podcast, Seth sits down with Kimberly Richardson, Assistant City Manager of Peoria, Illinois, to explore how strategic planning can become a powerful tool for developing leaders, strengthening collaboration, and changing how an entire organization works together.
Drawing from her experience across multiple Illinois communities, Kimberly shares how Peoria is moving beyond traditional strategic planning to build a culture where department leaders think beyond their individual responsibilities and take ownership of shared priorities.
But this conversation goes far beyond strategy. Kimberly opens up about her own leadership journey, the self-doubt that nearly caused her to walk away from local government, and the mentors who helped her recognize the leader she was capable of becoming.
From the importance of developing future leaders to the challenge of turning vision into meaningful action, this conversation is a reminder that the greatest opportunity in strategic planning may not be what your organization accomplishes, but who your people become in the process.
At the 2026 ICMA Annual Conference in Long Beach, California, Kimberly presented a skill-building workshop titled "From Vision to Department Results: Building Strategic Leaders and Action Plans Across All City Departments." The session explored how municipal leaders can move beyond traditional strategic planning to develop shared accountability, strengthen cross-departmental leadership, and turn community priorities into meaningful organizational action.
About Kimberly Richardson
Kimberly Richardson serves as Assistant City Manager for the City of Peoria, Illinois. With more than 20 years of experience in local government, her career has included leadership and operational roles in communities throughout Illinois, including Bensenville, Rockford, Riverside, Flossmoor, and Evanston. Her diverse experience spans economic development, public works, community engagement, technology, organizational operations, and executive leadership. She brings a unique perspective to municipal management, emphasizing relationship-building, leadership development, and collaboration across departments.
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. Join the Waitlist Here: 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: Talk Like TED
Episode 408 of The HaltingWinter Podcast
Most presentations are forgotten before the meeting ends. The ones people remember and pass along do something different.
This week in the MLDC, we're looking at Talk Like TED by Carmine Gallo, who studied more than 500 TED talks to find what makes a message stick. For local government leaders who present constantly, from council chambers to budget hearings to tense public comment periods, the answer matters more than you'd think.
The pre-order window is open for the Founding Collection of hats, t-shirts, and hoodies from the America Runs on Local Government campaign at shop.haltingwinter.com. Proceeds fund our work telling the stories of the people and projects that make our cities and counties function and flourish. Order before November 22nd!
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

Amy Snider: The Executive Leadership Trap
When Your Greatest Strength Becomes Your Team's Weakness
Episode 407 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

America Runs on Local Government. Now you can wear the message with pride and help us tell the stories behind it. Shop the limited-edition Founders Collection, available for preorder through November 22: https://shop.haltingwinter.com/
What if the very skills that made you successful are now holding your team back? In local government, the leaders who rise through the ranks are often the ones who know how to get things done. They solve problems, take ownership, and step in when things get difficult. But at the executive level, those same instincts can become a liability.
Amy Snider, Deputy City Manager for Harrisonburg, Virginia, joins Seth to explore one of the most overlooked challenges of executive leadership: knowing when to stop being the fixer.
Drawing from her unconventional journey through education, city, and county government, Amy challenges the idea that assistant and deputy city managers should function as super department heads. Their greatest value isn't knowing more than everyone else. It's creating the conditions for everyone else's expertise to work together.
Together, they explore the dangers of overfunctioning, the power of giving employees permission to innovate, and why communication, collaboration, and conflict resolution aren't simply soft skills; they're essential executive competencies.
Amy also shares insights from her ICMA Annual Conference session in Long Beach, "Assistant City Managers Are Not Super Department Heads: Understanding the Realities Behind the Title," which challenged municipal leaders to rethink the responsibilities, expectations, and skills that make assistant and deputy city managers effective.
If you've ever struggled to let go, delegate responsibility, or resist the temptation to solve every problem yourself, this conversation will challenge how you think about leadership.
About Amy Snider
Amy Snider serves as Deputy City Manager for the City of Harrisonburg, Virginia, where she oversees five departments: Public Works, Public Utilities, Public Transportation, Parks and Recreation, and Community Development. She brings a distinctive perspective to executive leadership, emphasizing relationship-building, facilitation, conflict resolution, and empowering department leaders to succeed.
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 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

Doreen Jokerst: Modernizing Policing from the Inside Out
A Better Future Begins with the People Behind the Badge
Episode 406 of The HaltingWinter Podcast
Sponsored by Tyler Technologies

America Runs on Local Government. Now you can wear the message with pride and help us tell the stories behind it. Shop the limited-edition Founders Collection, available for preorder through November 22: https://shop.haltingwinter.com/
What does it really take to modernize policing? New technology, better equipment, and updated policies are part of the equation, but Overland Park, Kansas, Police Chief Doreen Jokerst believes meaningful transformation begins somewhere else: with the people and culture inside the organization.
In this episode of The HaltingWinter Podcast, Doreen joins Seth Winterhalter to explore why the future of policing depends on intentional leadership, employee wellness, organizational trust, and a commitment to taking care of those who serve their communities.
Drawing on her experience in municipal and university policing, Doreen discusses the cumulative toll of public safety work, the importance of creating a culture where employees feel supported, and why leaders must model the very behaviors they expect from their teams.
She also shares her approach to building a strong partnership with the city manager, breaking down departmental silos, engaging community members through listening rather than defensiveness, and helping residents better understand the complexities of local government.
For city managers, police chiefs, department directors, and municipal leaders, this conversation offers a powerful reminder: You can't transform the services you provide without investing in the people who provide them.
About Doreen Jokerst
Doreen Jokerst serves as Chief of Police for the City of Overland Park, Kansas. Her law enforcement career includes nearly two decades with the Parker Police Department in Colorado and service as Chief of Police at the University of Colorado Boulder. A founding board member of The Curve, a nonprofit focused on advancing police leadership and organizational culture, Doreen is passionate about modernizing policing through intentional leadership, employee wellness, and meaningful community relationships.
At the 2026 ICMA Annual Conference in Long Beach, California, Doreen presented "Beneath the Surface: Understanding Policing Culture and What It Takes to Modernize It," a session examining the role of city managers in supporting police leadership, strengthening organizational culture, prioritizing employee wellness, and navigating the challenges of modern policing.
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. Join the Waitlist Here: 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: You're Not Listening
Episode 405 of The HaltingWinter Podcast
We think we're listening as long as we're not interrupting. But most of us are just waiting for our turn to talk, and in local government, that habit costs more than we realize. This week in the MLDC, Seth Winterhalter digs into You're Not Listening: What You're Missing and Why It Matters by journalist Kate Murphy, exploring what her two-year investigation into the science of listening reveals for city managers, county administrators, and department heads navigating council meetings, staff conversations, and public pushback. 
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