Why Retail Strategies Fail - Kevin Ertell Breaks Down The Strategy Trap

S2E2 Your Strategy Isn’t Failing - Your Execution Is. Here’s How to Fix It.

Most strategies don’t fail in the boardroom - they fail in the real world. In this episode of Retail Transformers, Ricardo and Casey sit down with Kevin Ertell, longtime retail operator and author of The Strategy Trap: Why Companies Fail at Execution and How to Get It Right. Kevin shares why 67% of well‑crafted strategies fail, the early warning signs leaders miss, and how his Six Cs framework helps teams turn strategy into real‑world results.

As Kevin explains, “Most strategies fail later, not loudly” - and the root cause is almost always poor execution, not bad ideas. Drawing from 30+ years at Nike, Sur La Table, Borders, and Tower Records, plus interviews with 60+ operators, Kevin breaks down how leaders can avoid the strategy trap and build strategies that humans can actually execute.

What We Cover

Why most strategies fail in execution, not planningThe Strategy Trap: what it is and how to avoid itThe Six Cs framework: Co‑creation, Clarity, Capacity, Communication, Coordination, CoachingWhy co‑creation is essential for execution successThe “tree stump theory” and how blind spots derail executionWhy leaders must “slow down to speed up”How culture, incentives, and communication shape executionReal‑world examples from Nike, Borders, and more

Why This Episode Matters

If you’re launching a new strategy this year. Or wondering why the last one didn’t land. This conversation gives you the tools, frameworks, and mindset to execute with confidence.

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About Our Guest