Municipal Leaders: Develop Faster, Lead Stronger, Build Better
Every week, you’ll get insights and actionable steps to help you navigate personal growth and professional success.
Episode 229 of The HaltingWinter Podcast
Brought to you by Zencity and Tyler Technologies
Most municipal leaders learn their craft in boardrooms, classrooms, or city council chambers. Jason Monroe learned his in burning buildings and on the back of an ambulance.
Before becoming City Manager of Frankfort, Kentucky, Jason spent more than two decades as a firefighter and paramedic. His career path was anything but conventional, beginning with an EMT class he took on a whim, leading to years of public safety service, and ultimately landing him in the city’s top leadership role.
In our conversation on The HaltingWinter Podcast, Jason reveals how the lessons forged in fire—adaptability, resilience, and clear-headed decision-making under pressure—continue to shape how he leads today.
Jason didn’t grow up aspiring to be a city manager. In fact, he didn’t even know what the role was. His early life was marked by constant change: 13 schools, four high schools, and a childhood of instability. That environment, however, gave him a gift: the ability to get comfortable being uncomfortable.
As a firefighter and paramedic, Jason found both family and purpose. He thrived in the chaos of emergency calls, the camaraderie of the firehouse, and the knowledge that when someone dialed 911, he was the one who showed up. Over time, he rose through the ranks—captain, assistant chief, fire chief—and then, unexpectedly, city manager.
Jason reminds us of something often forgotten: when first responders show up, they’re not just stepping into someone else’s worst day; they may be carrying one of their own.
“When you show up, you’re seeing people on their worst day. What a lot of people don’t understand is that could also be that firefighter’s worst day.”
It’s a sobering reality for fire and police personnel, who juggle family struggles, sleepless nights, and mental health challenges while being expected to perform flawlessly in crisis.
Like many municipal leaders, Jason has wrestled with the tension between action and bureaucracy. He was never afraid to question the rules:
“Why do we need an SOP on how to put gas in the ambulance? Because one person made a mistake? Why not address the individual instead of creating another policy?”
That willingness to challenge “the way we’ve always done it” is part of what propelled him forward. When Frankfort faced high turnover and low morale in its city manager’s office, Jason didn’t wait for someone else to step up. He raised his hand.
Jason’s journey is more than a personal story; it’s a leadership playbook for anyone in local government:
Frankfort may be a city of 30,000, but as Kentucky’s capital, its visibility—and its pressures—extend statewide. Jason’s story illustrates why leadership in local government isn’t just about technical skill. It’s about showing up with courage, clarity, and the willingness to command chaos.
Because at the end of the day, whether in a firehouse or a city hall, the call is the same: step up and lead.
Tyler Technologies
This episode is brought to you by Tyler Technologies, helping local governments create smarter, more connected communities through software that streamlines operations and enhances public trust. Learn more at tylertech.com.
Zencity
We’re also proud to partner with Zencity, the community engagement platform that helps public sector leaders hear from all residents—not just the “same ten voices.” Their tools make it easier to understand what your community really needs and act on it. Schedule a demo at zencity.io.
The HaltingWinter Podcast celebrates and elevates the people who power local government. Through in-depth conversations with leaders from cities, counties, and communities of all sizes, host Seth Winterhalter explores the journeys, challenges, and innovations happening in municipal leadership across America.
