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

Episode 187 of The HaltingWinter Podcast

In this episode, Seth Winterhalter sits down with Will Ibershof, City Administrator of Madras, Oregon—and former mayor of Duval, Washington—for a conversation that’s as raw as it is inspiring. From throwing up during his first campaign event to building parks, securing grants, and mentoring the next generation of public leaders, Will’s story is a powerful reflection on the real work of local government.

Will opens up about what it takes to lead with courage in small communities—especially through burnout, rapid growth, and the constant push-and-pull between progress and preservation. Whether you're an elected official, a department director, or aspiring to either, this episode offers a front-row seat to the challenges and rewards of leading where you live.

• From Dare to Duty: How a challenge from friends led Will to run for office despite never having attended a council meeting

  Doorbelling and Discomfort: The unforgettable (and stomach-turning) campaign moment that taught him the power of grit and authenticity

  No Administrator, No Problem: What it’s like to serve as an elected mayor and CEO in a city without a city manager or administrator

  Burnout and Regret: A candid look at the personal cost of public service and what Will wishes he had done differently

  Mentorship That Matters: How Will forged a powerful partnership with the City Manager of Bend, Oregon and why big-small city collaboration is a rising-tide strategy

  Rural Growth, Urban Expectations: Lessons from Sultan and Madras, where housing demand, infrastructure realities, and small-town identity collide

  The Heart of Connection: Why events, community grants, and everyday kindness are essential tools for cities battling isolation and division

LinkedIn: www.linkedin.com/in/willibershof

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 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 186 of The HaltingWinter Podcast
(Part 1 of 5: "Turn the Ship Around" Series)
Episode Title: Why Giving Up Control is the Boldest Leadership Move You Can Make

What if the key to stronger teams isn’t more control, but more trust?

In this opening episode of our 5-part series on Turn the Ship Around by David Marquet, Seth Winterhalter unpacks the transformative concept of “leader-leader” culture. Instead of the traditional “leader-follower” model, where a single person gives orders and everyone else executes, Marquet proposes something radically different: giving up control to create real ownership.

For local government leaders, where decisions are often high-stakes and staff are overextended, this model creates a blueprint for deeper engagement, higher competence, and more strategic thinking across all levels of your team.

• Why traditional leadership models limit growth, autonomy, and performance

• The difference between empowerment and actual transfer of control

• How pushing decision-making down creates buy-in and drives initiative

• Why control, clarity, and competence must move together

• The first steps to shifting your culture from passive compliance to active leadership

• Monday: Why control is overrated—and what to replace it with

• Tuesday–Thursday: Building clarity, competence, and initiative at every level

• Friday: From follower to leader—how to multiply leadership across your org

Join the Municipal Leadership Development Circle (MLDC) this week and unlock:
✔ All 5 podcast episodes from the Turn the Ship Around series
✔ Daily blog reflections and tools for implementation
✔ Friday’s Virtual Mastermind session
✔ Access to a growing nationwide community of local government leaders

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

• Book: Turn the Ship Around by L. David Marquet

• Weekly Blog & Newsletter: The Leader’s Lens

• MLDC Membership Details: www.haltingwinter.com/mldc

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

• Website: www.HaltingWinter.com

Episode 185 of The HaltingWinter Podcast

In this episode, Seth Winterhalter sits down with Christopher Gilbert, Township Administrator of Springfield Township, Ohio, to explore how customer service isn’t just a frontline task, it’s a leadership philosophy. With a background in engineering and a passion for systems, Chris shares how he led a cultural shift across the organization that made public service smoother, faster, and more human.

For Chris, the goal isn’t just “better service.” It’s building trust by making every city interaction feel respectful, responsive, and frictionless. This conversation is a masterclass in what it means to lead from the inside out—designing teams, training, and systems that turn municipal values into resident experiences.

• More Than Manners: Why Chris’s customer service initiative focused on culture, not scripts and how that changed everything

• Removing Friction: How Springfield redesigned internal workflows to make city services easier to access and navigate

• Cross-Department Consistency: What it takes to build a shared service philosophy across multiple teams and touchpoints

• Leadership Through Systems: Why good leaders don’t just solve problems—they create structures that solve them over and over

• Transparency as a Trust Strategy: How showing residents what’s happening behind the scenes strengthens public confidence

• From Tactical to Strategic: His journey from city engineer to city manager and how technical skills gave way to people-first thinking

LinkedIn: www.linkedin.com/in/christopher-gilbert

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 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 184 of The HaltingWinter Podcast

In this vulnerable and deeply reflective episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Milton Dohoney Jr., City Administrator of Ann Arbor, Michigan—a seasoned leader with decades of executive municipal experience and the hard-won wisdom that comes with it.

Milton doesn’t speak in buzzwords. He speaks in truth about the emotional cost of leadership, the isolation that often accompanies it, and the quiet weight leaders carry while holding their communities together. This conversation offers more than professional advice—it’s a powerful reminder of the humanity behind the title.

If you’ve ever felt unseen, stretched thin, or unsure whether the work you’re doing is truly making a difference, this episode is for you.

• “I didn’t come to keep the seat warm.”
  Milton shares what it means to take a leadership role seriously and why forward momentum is a responsibility, not a bonus.

• The Emotional Weight of Leadership
  From carrying team burdens to managing public pressure, Milton speaks openly about the isolation leaders rarely admit.

• Loneliness at the Top
  Why leadership doesn’t protect you from struggle and why sharing that truth can actually make you stronger.

• Reclaiming the Identity of Public Service
  Milton reflects on how the pride and perception of municipal leadership have changed and why it’s time to reignite the mission.

• Presence Over Visibility
  A subtle but vital distinction: real leaders don’t just show up—they connect, engage, and make people feel seen.

• The Power of Listening and Learning
  Milton shares how being fully present with residents and staff creates trust and resilience in times of uncertainty.

• Advice for Aspiring and Current Leaders
  “Don’t seek the title. Seek the transformation you can help bring about.”

LinkedIn: www.linkedin.com/in/milton-dohoney-jr

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 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 183 of The HaltingWinter Podcast
Citizens, Not Customers
(Part 1 of 5: "The New Public Service" Series)

In this opening episode of our latest MLDC series, Seth Winterhalter challenges one of the most common assumptions in local government leadership: that residents are customers and cities are service providers.

Drawing from The New Public Service by Janet and Robert Denhardt, Seth explores how this mindset, while well-intentioned, can unintentionally reduce civic participation, strain trust, and disconnect leadership from the very people it serves. In contrast, a citizen-centered approach invites collaboration, dialogue, and shared responsibility.

This episode will reset your frame and offer practical ways to lead with your community, not just for them.

• Residents are not consumers of city services—they are co-creators of community

• Treating people like customers centers transactions; treating them like citizens centers shared values

• “Public interest” isn’t discovered through surveys—it’s shaped through dialogue

• The goal of government isn’t just efficient service—it’s meaningful engagement

• Leadership in this framework shifts from “fixer” to facilitator of shared purpose

• Real trust is built when people feel included early, not just consulted late

Monday: Citizens vs. customers
Tuesday: Serving, not steering
Wednesday: Valuing people over productivity
Thursday: Engagement over control
Friday: Integrity and trust as culture-shaping leadership tools

This week only, unlock:

• All 5 podcast episodes in The New Public Service series

• Daily written reflections to help you implement what you’re learning

• Friday’s Virtual Book Club for live peer discussion

• Full access to the MLDC platform + national leadership network
  → Start your 7-day free trial now at HaltingWinter.com

• Book: The New Public Service by Janet & Robert Denhardt

• MLDC: The Municipal Leadership Development Circle

• Weekly Newsletter: The Leader’s Lens

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

• Website: www.HaltingWinter.com