EPISODE · Apr 27, 2026 · 49 MIN
Supervisors as teachers not bosses
from Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs · host Flying Whale Strategies
Frontline supervisors might be the key to our workplace culture. And they may need our attention. Supervisors are asked to do everything — schedule, train, manage quality, order supplies, write reports. And yet the one skill that might actually make their jobs easier is the one we almost never teach them: how to coach.Hillary thinks that the answer to your productivity challenges might not be more accountability, but more adult learning. She walks through the mechanics of in-the-moment reflection, a 30-second coaching practice that can dramatically shift a worker's motivation, and makes the case for internal certifications as a tool any organization can build, regardless of sector or budget.Then she hands the mic to her ex-wife, Steph Frances — founder of Prodigy Ventures and Little Square Studio— who has spent her career proving that the young adults most workplaces give up on are often the ones most hungry to grow.Some things you'll hear:How Prodigy reviewed footage of baristas working a rush, NFL-style, and why apprentices loved itWhat happened when a shift leader jumped over the espresso counter at a customer — and how that became a breakthrough coaching momentWhy one apprentice literally sprinted to work, and what that tells us about intrinsic motivationThe difference between a "blue ribbon for showing up" culture and one where people actually want to get betterHow to build an internal certification from scratch using questions you can ask your own supervisors this weekGuest: Steph Frances is the founder of Prodigy Ventures, a social enterprise and apprenticeship for young adults in northeast Denver. Over eight years as Executive Director, Steph led Prodigy’s enterprise to double-digit year-over-year sales growth, raised over $5M and built an apprenticeship model for disconnected youth with an 85% completion rate. Most recently, Steph served as the National Vice President of Programs and Training for Momentum Advisory Collective, the capacity-building organization for Cafe Momentum. In her role as a consultant over the past ten years, Steph has worked with social enterprises around the country, most closely with REDF ESEs in start-up, program development, certification, strategic planning and fundraising.Steph is also a proud 2020 Livingston Fellow, and a Denver Business Journal Outstanding Women in Business finalist. She was trained at Eagle Rock’s School of Professional Studies, has a Master’s in Nonprofit Management from Regis University and is an altMBA graduate. Steph also serves on the Board of Directors for BuCu West, a community-based economic development organization in Denver’s Westwood neighborhood; she is also a member of the Globeville, Elyria, Swansea Community Investment Fund at National Western Authority.Get in touch
What this episode covers
Frontline supervisors might be the key to our workplace culture. And they may need our attention. Supervisors are asked to do everything — schedule, train, manage quality, order supplies, write reports. And yet the one skill that might actually make their jobs easier is the one we almost never teach them: how to coach. Hillary thinks that the answer to your productivity challenges might not be more accountability, but more adult learning. She walks through the mechanics of in-the-moment refle...
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Supervisors as teachers not bosses
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