December 09, 2025

266: Rebecca Grill: Running Toward the Storm

1 hour 22 minutes

Rebecca Grill: Running Toward the Storm The "Be the Buffalo" Approach to City Management

Episode 266 of The HaltingWinter Podcast Brought to you by Tyler Technologies

When you meet a city manager who has served inside youth correctional facilities, rebuilt broken licensing systems, modernized city hall after a cybersecurity crisis, and navigated budgets where every dollar feels political, you quickly understand why she talks about leadership the way she does.

In this episode, Rebecca Grill, City Manager of Oshkosh, Wisconsin, shares the story behind her "be the buffalo" leadership mantra: when the storm comes, run toward it.

Rebecca opens up about the early experiences that shaped her resilience, from working with vulnerable youth to responding to neighborhood crises in Milwaukee's housing authority. She reflects on the lessons learned from clerking in high-pressure environments, leading after a 33-year administrator, modernizing systems that were decades behind, and stepping into a true city manager role where public visibility is a daily reality.

We talk about courage, continuous improvement, technology adoption, customer experience, and why real change requires breaking old systems without breaking people. Rebecca also shares candid insights on the unique pressures women face in city management and how she stays grounded when the job demands feel endless.

If you're a city manager, an aspiring leader, or anyone who understands the weight of public service, this episode will encourage you, challenge you, and give you a renewed sense of purpose.