Getting Your Strategy Right With Kevin Ertell

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Mar 8, 2026

Kevin Ertell, founder of Mistere Advisory and author of The Strategy Trap, is a veteran retail and e-commerce operator. He talks about why execution—not ideas—fails. He covers incentives that shape behavior, co-creation and the 70% aligned rule, slowing down to create clarity, testing with frontline teams, and using AI to multiply time and insight.

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ADVICE

Design Incentives Across Three Axes

Do design incentives across financial, social, and convenience axes to align behavior with strategy.
Example: at Sur La Table Kevin gave stores extra payroll hours for nearby online orders to involve and motivate store teams.

INSIGHT

Execution, Not Ideas, Is The Main Failure Mode

Insight: Most strategies fail not because ideas are bad but because execution is poor and conditions for humans to act weren't created.
Kevin interviewed 60+ operators to build practical execution frameworks rather than academic models.

ADVICE

Slow Down To Speed Up

Do slow down to speed up: pause to create clarity and remove barriers before wide implementation.
Kevin warns rushing causes worse slowdowns later; you must clear space and align people first.

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Welcome to episode #1026 of Thinking With Mitch Joel (formerly Six Pixels of Separation).

At a time when strategy has become a kind of corporate theater… carefully crafted presentations, ambitious roadmaps and bold declarations that rarely survive first contact with reality… Kevin Ertell has spent a career focused on the harder question: why execution so often fails. Kevin is the Founder and CEO of Mistere Advisory and a veteran operator whose three decades of experience include leading large-scale retail and e-commerce operations at global brands like Nike, Sur La Table, Borders, and Tower Records. Over the years he has developed a reputation as a straight-talking advisor who helps leaders turn complexity into clarity and ambition into measurable results. His work spans industries including technology, healthcare, retail, consumer goods and manufacturing, where he focuses on helping organizations align teams, simplify priorities and build the operating rhythms required to deliver on their plans. In his new book, The Strategy Trap - Why Companies Fail at Execution and How to Get It Right, Kevin draws on decades of frontline experience to tackle a frustrating reality of modern business: most strategies don't fail on paper… they fail in the real world. Through practical frameworks like his Six Cs of Execution (Co-creation, Clarity, Capacity, Communication, Coordination and Coaching) he argues that strategy and execution must begin in the same room, with teams co-creating the plan and committing to disciplined follow-through. Kevin explores how incentives shape behavior, why organizations must slow down to create clarity before accelerating, and how leadership cultures built around coaching and collaboration can unlock real momentum. Grounded in operational experience rather than theory, his work reframes strategy not as a planning exercise but as a team sport that requires alignment, accountability and relentless focus on execution. Enjoy the conversation…

Running time: 58:44.
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The Strategy Trap - Why Companies Fail at Execution and How to Get It Right.
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Chapters:

(00:00) - Introduction to Kevin Ertell and his Expertise. (02:51) - The Evolution of E-commerce and Digital Strategy. (06:03) - Understanding the Strategy Trap. (08:57) - The Importance of Execution in Strategy. (12:02) - Communication and Team Dynamics in Strategy. (14:47) - Co-Creation and Employee Engagement. (17:55) - The Role of Customers in Strategy. (21:04) - Defining the Strategy Trap and Its Implications. (30:01) - Navigating Change: The Role of Detractors in Strategy. (32:47) - The Rise and Fall of Retail Giants: Lessons from JCPenney. (40:58) - Harnessing AI: Transforming Strategy and Productivity. (49:01) - Coaching Mindset: The Key to Effective Leadership. (53:06) - Anticipating the Future: Understanding Change and Context.