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 planning
The Strategy Trap: what it is and how to avoid it
The Six Cs framework: Co‑creation, Clarity, Capacity, Communication, Coordination, Coaching
Why co‑creation is essential for execution success
The “tree stump theory” and how blind spots derail execution
Why leaders must “slow down to speed up”
How culture, incentives, and communication shape execution
Real‑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
Kevin Ertell, https://www.linkedin.com/in/kevinertell/
Author, The Strategy Trap: Why Companies Fail at Execution and How to Get It Right. https://a.co/d/04AqxywE
Founder & CEO, Mistere Advisory. https://www.mistereadvisory.com

Kevin Ertell is a veteran executive and trusted advisor with more than 30 years of experience leading transformations at brands like Nike, Tower Records, and Sur La Table. As founder and CEO of Mistere Advisory, he helps companies of all sizes bring clarity, alignment, and action to their strategies. Known for his straight talk, practical insight, and ability to cut through complexity, Kevin draws on deep experience across leadership, operations, and digital growth to help teams turn ideas into results. When he’s not helping companies get unstuck, he’s likely playing bass, cooking for family, or following Cleveland sports with stubborn optimism.

Chapters

(00:00) Preview Teaser

(01:22) Show Intro

(04:21) Welcome Kevin Ertell to the Retail Transformers Podcast

(07:54) The Strategy Trap: An Introduction

(10:15) Common Pitfalls in Strategy Execution

(11:53) Techniques for Successful Execution

(14:58) The Six Cs Framework

(24:13) The Importance of Co-Creation, Clarity, and Capacity

(25:29) Showtime: Communication, Coordination, and Coaching

(26:31) Coaching as a Leadership Tool

(27:30) Real-World Example: Borders Rewards Program

(30:56) Key Decisions Before Strategy Kickoff

(32:41) Slowing Down to Speed Up

(37:23) The Role of Company Culture

(39:03) AI in Strategy Execution

(41:41) Conclusion and Final Thoughts

(44:08) Show Close

Meet Your Hosts
Helping you stay sharp, be bold, and transform retail:

Ricardo Belmar is an NRF Top Retail Voice for 2025 and a RETHINK Retail Top Retail Expert from 2021 – 2026. Thinkers 360 has named him a Top 10 Thought Leader in Retail, a Top 25 Thought Leader in AGI and Careers, a Top 50 Thought Leader in Agentic AIand Management, and a Top 100 Thought Leader in Digital Transformation and Transformation. Thinkers 360 also named him a Top Digital Voice for 2024 and 2025. He is an advisory council member at George Mason University’s Center for Retail Transformationand the Retail Cloud Alliance. He was most recently the partner marketing leader for retail & consumer goods in the Americas at Microsoft.

Casey Golden, is the North America Leader for Retail & Consumer Goods at CI&T, and CEO of Luxlock. She is a RETHINK Retail Top Retail Expert from 2023 - 2026, and Retail Cloud Alliance advisory council member. After a career on the fashion and supply chain technology side of the business, Casey is obsessed with the customer relationship between the brand and the consumer and is slaying franken-stacks and building retail tech!

Episode Music

Includes music provided by imunobeats.com, featuring Tropikool, from the album Future Beats 2, plus Virtual Apology and New Styles, from the album Shimmer Pop, written by Heston Mimms, published by Imuno.