Why Leaders Keep Falling into the Trap

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.