Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 350 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
Local government has a leadership problem. Not because leaders aren’t capable. Not because they don’t care. Not because they aren’t working hard enough.
The problem is that too many leaders feel responsible for having all the answers.
And the longer they lead, the heavier that burden becomes.
In Episode 350 of The HaltingWinter Podcast, I sat down with Sabrina Cotta, City Manager of Ashland, Oregon, to discuss her unique journey into local government and one of the most important leadership lessons she has learned along the way:
The best leaders don’t have all the answers.
In fact, some of the strongest organizations are built by leaders who recognize that the best ideas often come from the people closest to the work.
Throughout our conversation, Sabrina shared how experiences in military intelligence, county government, budgeting, strategic planning, human resources, and city management shaped her perspective on leadership. While her path wasn’t a straight line, it gave her something many leaders need more of: the ability to ask better questions.
One question in particular stood out: “Why do we do it this way?”
It’s a simple question, but one that has the power to unlock innovation, challenge outdated assumptions, and improve organizational performance.
Too often, leaders assume their role is to provide solutions. Sabrina argues that leadership is often about creating the conditions for solutions to emerge.
The employees answering phones, maintaining infrastructure, processing permits, repairing equipment, serving residents, and managing daily operations often see opportunities that executives never will. They’re closest to the challenges. They’re closest to the inefficiencies. They’re closest to the work.
The question is whether leadership is willing to listen.
Our conversation also explored several realities facing local government leaders today:
Perhaps most importantly, Sabrina reminds us that local government leadership isn’t about being the smartest person in the room. It’s about building a room full of smart people who are empowered to contribute.
If you’re a city manager, county administrator, department head, supervisor, or emerging leader, this episode will challenge how you think about leadership, innovation, and the role you play in helping others succeed.
Because better solutions rarely start at the top. They start with the people doing the work.
Listen to Episode 350: Sabrina Cotta: The Best Leaders Don’t Have All the Answers
This episode is sponsored by Tyler Technologies, the leader in empowering the public sector with software solutions that connect data, streamline operations, and improve service delivery. From AI to budgeting solutions, Tyler helps local governments build stronger, more resilient communities. Learn more at tylertech.com/winter →
The MLDC is where local government leaders go to grow, together. It’s the fastest-growing leadership development community designed specifically for the public sector, now paired with a comprehensive 9-month Leadership & Culture Program for those ready to elevate their leadership and their organization. Learn more at haltingwinter.com/mldc →
The HaltingWinter Podcast shines a spotlight on the people behind our cities and counties. Through candid conversations with local government leaders from across the nation, host Seth Winterhalter explores the journeys, challenges, and ideas shaping stronger communities while inspiring the next generation of public servants.
