Jennifer Callaway: Leading What You Don't Know
Why Great Leaders Trust People More Than Their Own Expertise

Episode 316 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Most leaders feel the pressure to have the answers. To be the expert. To walk into every room with clarity, confidence, and control.

But what if that's not what great leadership actually requires?

In this conversation, Seth Winterhalter sits down with Jennifer Callaway, Town Manager of Truckee, California, who shares a different path, one shaped not by expertise but by trust. Trust in her team. Trust in the process. And trust in the idea that leadership isn't about knowing everything…it's about creating the conditions for others to thrive.

From starting her career with no clear awareness of local government, to leading complex challenges around housing, tourism, and community identity, Jennifer offers a grounded and honest look at what it really takes to lead in today's environment.

This episode explores the shift from doer to leader, the discipline of listening to understand, and why some of the most impactful decisions aren't driven by technical knowledge, but by people.

If you've ever felt the weight of needing to have it all figured out…this conversation will challenge that assumption and offer a better way forward.

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

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

Show Notes: MLDC Book of the Week – Leading With Questions
Episode 315 of The HaltingWinter Podcast

Most local government leaders were promoted because they had the best answers. But what if that instinct—the automatic move toward the answer—is quietly limiting the people around you?

In this episode, Seth Winterhalter introduces the MLDC book of the week: Leading with Questions by Michael J. Marquardt. It's a book about one of the most common and most costly habits in leadership, and why the shift from answer-giving to question-asking may be the highest-leverage move available to local government leaders today.

If you want to go deeper, the MLDC is exploring the insights from this book all week through daily blog posts, podcast episodes, and implementation tools built specifically for city and county leaders. Learn more at HaltingWinter.com/MLDC.

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: Leading With Questions by Michael J. Marquardt

Connect with Seth Winterhalter

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

Peter Pirnejad: Leading Before You're Ready
The Hidden Crisis Facing the Next Generation of City Managers

Episode 314 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Local government leadership has changed. Not gradually. Not subtly. But quickly and in ways most leaders weren't prepared for.

In this episode, Seth Winterhalter sits down with Dr. Peter Pirnejad, former city manager and now Executive Director of the Davenport Institute, to unpack what's really happening inside today's cities and counties.

Leaders are stepping into roles earlier than ever before. The expectations are higher. The pressure is heavier. And the environment they're walking into is marked by distrust, disruption, and constant change.

The result?

Many are being asked to lead before they've had the time—or training—to truly be ready. But this isn't a conversation about failure. It's a conversation about reality.

Peter shares insights from nearly three decades in local government, the private sector, and academia to help leaders understand:

• Why the traditional path to leadership is disappearing
• How the role of the city manager has shifted from operational to deeply relational
• What it actually takes to build trust in today's climate
• And why the future of local government depends on developing leaders differently

Because while the work has changed…the mission hasn't.

If you're serving in local government or preparing to step into greater responsibility, this is a conversation that will help you lead with greater clarity, awareness, and intention.

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

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