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EP335 - Kevin Ertell The Strategy Trap

The Jason & Scot Show · with Kevin Ertell · February 3, 2026 · 56 min

Summary

This episode with Kevin Ertell, author of 'The Strategy Trap,' is a must-listen for ecommerce operators. It dissects why even brilliant strategies often fail due to poor execution and offers a practical framework to avoid common pitfalls. Learn how to translate vision into tangible results by focusing on co-creation, clarity, and capacity, then driving execution through effective communication, coordination, and coaching.

Key takeaways

Themes

leadership & managementorganizational developmentstrategic execution

Topics covered

6 cs frameworkco-creation in strategycoaching for executioncommunication in executioncoordination in executionecommerce leadershipexecution failureorganizational capacityretail strategystrategic claritystrategy trap book

Episode description

EP335 - Kevin Ertell The Strategy Trap http://jasonandscot.com In this electrifying episode of the Jason & Scot Show, recorded on Friday, October 10th, 2025, hosts Jason "Retailgeek" Goldberg and Scot\t Wingo welcome a very special guest and longtime friend, Kevin Ertell. With over 30 years of combined history, the duo dives into Kevin's impressive career trajectory, his extensive experiences in retail and strategy execution, and the valuable insights behind his newly released book, "The Strategy Trap: Why Companies Fail at Execution and How to Get It Right." Kevin's impressive background spans from starting at Tower Records to holding senior positions at iconic companies like Borders, Nike, and Sur La Table. He discusses his evolution in the retail space, the intricacies of establishing the first TowerRecords.com site, and his current role advising various businesses, including helping the Minnesota Timberwolves with their ticketing operations. As he unveils his book, listeners learn about the core theme: effective execution is the linchpin of successful strategy. Kevin breaks down the key concepts of his book, structured around the "six C's" that are critical for avoiding common pitfalls in strategic execution—co-creation, clarity, capacity, communication, coordination, and coaching. He emphasizes the importance of bringing teams together in the co-creation phase to ensure buy-in and alignment on the strategy, a central pillar in fostering commitment across the organization. The conversation touches on the significance of clarity in communication and the necessity of creating a space for people to provide feedback and understand their roles. Throughout the episode, Scot and Jason explore Kevin's practical stra

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Frequently asked about this episode

What does this episode say about leadership & management?
Implement the '6 Cs' framework (Co-creation, Clarity, Capacity, Communication, Coordination, Coaching) to improve strategic execution and avoid common traps.
What does this episode say about organizational development?
Prioritize co-creation in strategy development to foster alignment, buy-in, validation, and commitment across all levels and functions of your organization.
What does this episode say about strategic execution?
Ensure strategic clarity by simplifying your message and helping team members connect their personal meaning to the vision, leading to better retention and understanding.
What does this episode say about leadership & management?
Actively manage capacity, recognizing that new strategies require dedicated space and resources; avoid simply piling new initiatives on existing workloads.
What does this episode say about leadership & management?
Leverage the book as a reference tool; its structure, with a 'C-word' and associated 'trap' for each concept, allows for quick problem-solving when execution issues arise.

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