"Best Boss, Worst Boss!" The Interview Question That Exposes Every Bad Hire | Industry Spotlight

"Best Boss, Worst Boss!" The Interview Question That Exposes Every Bad Hire | Industry Spotlight

July 18, 2026 · 39 min

About this episode

This episode discusses a key interview question that reveals insights about potential hires and emphasizes the importance of transparency and accountability in the automotive industry.

In this episode of the Industry Spotlight, joining host Sam D'Arc are Bill O'flanagan, Dealer Principal at Reedman Toll Auto Group, and Todd Kaminski, Head of Direct Markets at Zurich North America to discuss the one interview question that predicts almost everything about whether a new hire will thrive or wash out, and why building a culture of transparency and daily accountability is the real fix for automotive's turnover problem. O'Flanagan shares his go-to interview question, "Who was your best boss and why, and who was your worst boss and why," and explains how the answer tells him everything he needs to know about how someone wants to be managed. He also breaks down why he shares full financial statements with every manager, a move his peers once called "insane," and how a daily 10-minute results call with every manager helped seven of his ten service centers set growth records this year. Kaminski adds a rare outside view from three decades working inside dealerships on why transparency, meritocracy, and recognition are what separate cultures that retain talent from those that don't. This episode of the Car Dealership Guy Podcast is brought to you by Zurich North America…

People in this episode

Host: Sam D'Arc

Guests: Bill O'flanagan, Todd Kaminski

Topics covered

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Sponsors

Zurich North America

Mentioned in this episode

Organizations: Reedman Toll Auto Group

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