Assumptions Create Execution Gaps

Why do smart strategies fail so often? According to Kevin Ertell, the problem isn’t a lack of ideas—it’s execution.

In this Encore episode of The Voice of Retail, Michael LeBlanc sits down live in person at the NRF Big Show in New York in The Remarkable Retail Narvar podcasting studio with Kevin Ertell, founder of Mistere Advisory, veteran retail operator, and former Vice President of Global Retail at Nike. Kevin is also the author of the new book The Strategy Trap: Why Companies Fail at Execution and How to Get It Right, which draws on more than two decades of hands-on leadership experience across iconic retail brands including Tower Records, Borders, Sur La Table, and Nike.

Kevin explains how organizations fall into the “strategy trap”—a tendency to over-invest in ideas, decks, and executive alignment while underestimating the human and organizational work required to execute effectively. He argues that strategy should be treated as the first step of execution, not as a theoretical exercise completed before real work begins.

Using well-known retail case studies, including the failed transformation of JCPenney, Kevin illustrates how untested assumptions, poor internal alignment, and misunderstanding customer behavior can derail even bold strategies. Leaders often assume that communication equals understanding, when in reality teams fill in the gaps with their own interpretations—creating misalignment that only becomes visible once execution is underway.

The conversation introduces Kevin’s practical “Six Cs of Execution” framework. The first phase—co-creation, clarity, and capacity—focuses on setting the stage by involving the right people, defining priorities, and making space for execution. The second phase—communication, coordination, and coaching—highlights the role of active leadership in sustaining momentum and course-correcting as conditions change.

Kevin also shares actionable tools leaders can use immediately, including structured problem-definition sessions, force-ranking priorities, and creating safe environments where teams can challenge assumptions. He emphasizes that focus is a leadership discipline—and that trying to pursue too many initiatives at once almost guarantees failure.

For retail leaders navigating AI disruption, economic volatility, and shifting consumer expectations, this episode offers a clear, operator-led blueprint for escaping the strategy trap and turning strategy into results.

Presented by Konek, Canada's Way to Pay. Visit Konek.ca to learn more.

Michael LeBlanc is the president and founder of M.E. LeBlanc & Company Inc, a senior retail advisor, keynote speaker and now, media entrepreneur. He has been on the front lines of retail industry change for his entire career.

Michael has delivered keynotes, hosted fire-side discussions and participated worldwide in thought leadership panels. He brings 25+ years of brand/retail/marketing & eCommerce leadership experience with Levi's, Black & Decker, Hudson's Bay, CanWest Media, Pandora Jewellery, The Shopping Channel and Retail Council of Canada to his advisory, speaking and media practice.

Michael produces and hosts a network of leading retail trade podcasts, including the award-winning No.1 independent retail industry podcast in America, Remarkable Retail with his partner, Dallas-based best-selling author Steve Dennis; Canada's top retail industry podcast The Voice of Retail and Canada's top food industry and one of the top Canadian-produced management independent podcasts in the country, The Food Professor with Dr. Sylvain Charlebois from Dalhousie University in Halifax.

Rethink Retail has recognized Michael as one of the top global retail experts for the fifth year in a row, the National Retail Federation has designated Michael as on their Top Retail Voices for 2025 and 2026. Thinkers 360 has named him on of the Top 50 global thought leaders in retail. If you are a BBQ fan, you can tune into Michael’s cooking show, Last Request BBQ, on YouTube, Instagram, X and yes, TikTok.

Michael is available for keynote presentations helping retailers, brands and retail industry insiders explaining the current state and future of the retail industry in North America and around the world.