Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Episode 316 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
Most leaders feel like they’re supposed to have the answers.
That’s the pressure that comes with the role.
You’re the one people look to.
The one expected to solve problems, make decisions, and move things forward.
But what if that pressure is actually leading you in the wrong direction?
In this episode of The HaltingWinter Podcast, Jennifer Callaway, Town Manager of Truckee, California, offers a different perspective—one shaped not by having all the answers, but by learning how to lead without them.
Her journey didn’t follow a straight line. She didn’t grow up aspiring to local government. She didn’t start out with a clear plan to become a town manager. But along the way, she discovered something that many leaders miss:
Impact doesn’t come from expertise.
It comes from people.
Whether she was stepping into roles outside her experience, navigating the complexity of a tourism-driven community, or tackling one of the most pressing challenges in local government, Jennifer learned that leadership isn’t about being the smartest person in the room.
It’s about asking better questions.
Listening longer than feels comfortable.
And trusting the people around you to carry what you don’t know.
That shift, from proving your expertise to empowering others, is what defines great leadership.
And it’s not easy.
Because it requires letting go of control.
Letting go of certainty.
And in some cases, letting go of the identity that got you to where you are.
But on the other side of that shift is something better:
Stronger teams.
Better decisions.
And a level of impact you can’t reach on your own.
If you’ve ever felt the pressure to have it all figured out…
this conversation will challenge that instinct and give you a more sustainable way to lead.
Listen to Episode 316: Jennifer Callaway: Leading What You Don’t Know
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 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.
