The Voice of Retail

The Strategy Trap: Why Companies Fail At Execution and How To Get It Right with Retail Veteran Kevin Ertell (Encore)

4 snips
Aug 7, 2026
Kevin Ertell, retail operator and founder of Mistere Advisory, draws on leadership roles at Tower Records, Borders, Sur La Table, and Nike to explore why smart strategies stall. He examines JCPenney’s transformation missteps, the dangers of untested assumptions, and how communication gaps derail teams. Ertell introduces his Six Cs of Execution, plus practical ways to prioritize, co-create, and define problems before pursuing solutions.
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INSIGHT

Execution Matters More Than Strategy Theory

  • Execution failures usually reflect weak implementation rather than bad strategy.
  • Kevin Ertell interviewed over 60 operators to make his framework practical and operator-led.
INSIGHT

Communication Does Not Guarantee Understanding

  • Leaders often mistake hearing agreement for genuine understanding.
  • Teams fill communication gaps with their own interpretations while executives assume everyone understood the strategy.
ANECDOTE

JCPenney Learned Coupons Were Part Of The Product

  • JCPenney eliminated coupons through its Fair and Square strategy without testing customer response.
  • Customers valued the thrill of finding deals, while the company failed to account for differences between JCPenney and Apple.
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