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Episode 404 of The HaltingWinter Podcast
Sponsored by Tyler Technologies
How many difficult council meetings could have gone differently if the right conversations had happened beforehand?
A council member challenges staff from the dais. An unexpected objection derails a carefully prepared proposal. Political tensions turn what should have been a productive meeting into an exhausting evening.
For many city managers, these situations feel like an unavoidable part of the job.
But what if they aren’t?
After 20 years as City Manager of Tualatin, Oregon, Sherilyn Lombos has developed a leadership practice she believes every city manager should prioritize: regular, intentional one-on-one conversations with elected officials.
Not simply to review agendas or share updates. To build something far more valuable.
Trust.
And Sherilyn knows that trust doesn’t eliminate political disagreements. But it can fundamentally change how those disagreements unfold.
In Episode 404 of The HaltingWinter Podcast, Sherilyn joins me to explore the conversations that happen before the council meeting, why they’re sometimes the hardest part of her job, and how they’ve shaped two decades of leadership.
We also explore a question that every long-serving leader eventually faces: What will remain of your leadership when you’re no longer there?
From navigating political relationships to building organizational culture and finding resilience when leadership gets difficult, Sherilyn offers a perspective shaped by 20 years in the same community.
Sherilyn presented at the 2026 ICMA Annual Conference in Long Beach. Her session, “How to Make Your One-on-Ones with Your Elected Officials Really Count,” takes a deeper look at one of the central leadership practices discussed in this episode.
Prefer to listen? Play the full episode using the audio player below.
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 Masterminds place local government leaders into small, intentionally curated cohorts with peers who understand the weight and challenges of your unique work. It’s a trusted room to wrestle with specific challenges, gain perspective from leaders across the country, and build the relationships that make you better at what you do. 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.
