Episode 190 of The HaltingWinter Podcast

In this episode, Seth Winterhalter sits down with Michael Herbert, Town Manager of Ashland, Massachusetts, for one of the most powerful conversations we’ve had on the podcast to date.

Michael’s story isn’t just about policy or public administration—it’s about personal transformation. From struggling with addiction and homelessness to becoming a respected municipal leader, Michael shares how hitting rock bottom gave him the perspective, resilience, and purpose he now brings to his role every day.

We talk about the long arc of recovery, the slow work of rebuilding a town’s identity, and the courage it takes to lead with transparency even when it’s unpopular.

If you’ve ever wondered how someone’s past can shape their impact or how small towns can create big change, this episode is a must-listen.

From Rock Bottom to Town Hall:
Michael opens up about the lowest point in his life and the decision that helped him climb out and into a career of public service.

The Long Game of Leadership:
Why real change in local government requires patience, persistence, and a willingness to plant trees you may never sit under.

The Price and Power of Transparency:
An honest look at the emotional cost of being open with residents and why Michael believes it’s still worth it.

A New England Perspective:
What it means to lead in a “Open-Town-Meeting” form of government, and how tradition shapes leadership expectations in Massachusetts.

LinkedIn: www.linkedin.com/in/michael-herbert

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

At HaltingWinter, we help local government leaders build thriving teams and resilient workplace cultures through keynotes, workshops, and leadership development programs rooted in the ABCs of Impactful Leadership.

Learn more at HaltingWinter.com

2025 South Carolina APWA Chapter Annual Conference
June 24 | Spartanburg, SC
Details at SCAPWA

2025 Kentucky League of Cities Annual Conference & Expo
September 24 | Owensboro, KY
Details at KLC

2025 Kansas City/County Management Association Annual Conference
December 4 | Manhattan, KS
Details at KCMA

The Municipal Leadership Development Circle (MLDC) is where municipal leaders grow together through weekly podcasts, curated book insights, and a nationwide peer community focused on real leadership, real culture, and real conversations.

Secure Your Summer Special and Start Your FREE 7-day trial
Join the MLDC

Episode 189 of The HaltingWinter Podcast
(Part 1 of 5: Dare to Lead Series)
Episode Title: Leadership Requires Vulnerability

If you think leadership is about power and perfection, think again.

In this first episode of our five-part series on Brené Brown’s Dare to Lead, Seth Winterhalter explores the foundational—and often uncomfortable—idea that real leadership begins with vulnerability. In the public sector, where scrutiny is constant and mistakes are public, vulnerability can feel risky. But according to Brown’s research, it’s also the birthplace of innovation, trust, and courageous leadership.

This episode unpacks what vulnerability really is (and isn’t), and how it becomes the foundation for stronger teams, braver conversations, and more resilient cultures in local government.

• Why vulnerability is the prerequisite for trust, connection, and accountability

• The difference between oversharing and leading with openness

• How fear of failure and self-protection erode effective leadership

• Why leaders who avoid vulnerability often create cultures of silence and burnout

• How embracing discomfort leads to better decisions and stronger relationships

• Monday: The myth of strength vs. the reality of vulnerability in leadership

• Tuesday–Thursday: Digging into courage, trust-building, and fear-based leadership traps

• Friday: Live Virtual Mastermind – Peer reflection, challenges, and implementation strategies

Join the Municipal Leadership Development Circle and get access to:
✔ All five episodes in the Dare to Lead podcast series
✔ Daily blog reflections and implementation guides
✔ Friday’s national Virtual Book Club
✔ A thriving network of city managers and municipal leaders across the U.S.

➡ Start your free 7-day trial now at HaltingWinter.com/MLDC

• Book: Dare to Lead by Brené Brown

• Learn more: www.haltingwinter.com/mldc

• Weekly Newsletter: The Leader’s Lens

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

• Website: www.HaltingWinter.com

Episode 188 of The HaltingWinter Podcast

In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Dalton Pierce, City Manager of York, South Carolina, to explore the leadership tensions every municipal executive knows too well: how do you balance the urgency to improve with the patience required to bring people along?

Dalton shares his journey from city planner to city manager, and how that unique path shapes his approach to decision-making, team building, and navigating the political and personal complexities of local government. His insights on culture, hiring, and pace will resonate with leaders at every level—especially those who feel the pull between visionary change and community trust.

• Planning Roots, Manager Realities
  How Dalton’s background in planning helps him hold the long-term vision while managing short-term demands.

• The Pace of People
  The leadership lesson that transformed his mindset: lasting progress happens at the speed of trust, not the speed of urgency.

• Culture Over Credentials
  Why hiring people who align with values, not just skillsets, is one of his top priorities as a leader.

• The Isolation of Leadership
  Dalton reflects on the quiet challenges of being a city manager and why honest conversations with peers can be lifesaving.

• Public Service with a Purpose
  The difference between checking boxes and creating buy-in—and why your team, not your title, defines your success.

LinkedIn: www.linkedin.com/in/dalton-pierce

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

At HaltingWinter, we help local government leaders build thriving teams and resilient workplace cultures through keynotes, workshops, and leadership development programs rooted in the ABCs of Impactful Leadership.

Learn more at HaltingWinter.com

2025 South Carolina APWA Chapter Annual Conference
June 24 | Spartanburg, SC
Details at SCAPWA

2025 Kentucky League of Cities Annual Conference & Expo
September 24 | Owensboro, KY
Details at KLC

2025 Kansas City/County Management Association Annual Conference
December 4 | Manhattan, KS
Details at KCMA

The Municipal Leadership Development Circle (MLDC) is where municipal leaders grow together through weekly podcasts, curated book insights, and a nationwide peer community focused on real leadership, real culture, and real conversations.

Secure Your Summer Special and Start Your FREE 7-day trial
Join the MLDC