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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 leaders grappling with failed initiatives. Ertell, a veteran of retail giants like Tower Records, Borders, Sur La Table, and Nike, dissects why strategies falter at the execution stage and provides a practical framework (the 'Six Cs') to ensure your strategic plans translate into tangible results. He emphasizes moving beyond just ideation to actively creating the conditions for successful implementation, offering actionable advice for leaders to overcome common pitfalls and foster a culture of strategic execution.

Key takeaways

Themes

founder & leadershipdtc strategy

Topics covered

strategic execution frameworksovercoming execution failureco-creation in strategyorganizational alignmentleadership and strategy implementationcapacity planning for new initiatives

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 founder & leadership?
Prioritize co-creation in strategy development to build alignment, buy-in, and commitment across all levels and functions of the organization. This ensures the strategy is workable and deeply understood.
What does this episode say about dtc strategy?
Simplify your strategy for clarity and help employees connect their personal meaning to the overarching vision. This significantly improves retention and engagement with the strategic goals.
What does this episode say about founder & leadership?
Actively manage capacity by creating dedicated space for new strategic initiatives. Avoid simply layering new work on top of existing workloads, which often leads to burnout and failed execution.
What does this episode say about founder & leadership?
Implement the 'Six Cs' framework (Co-creation, Clarity, Capacity, Communication, Coordination, Coaching) to structure your strategic execution process. Each 'C' addresses a critical aspect of moving from planning to successful implementation.
What does this episode say about founder & leadership?
Utilize Ertell's book, 'The Strategy Trap,' as a practical reference guide for identifying and escaping common execution pitfalls. The book's structure allows for targeted solutions to specific 'traps' organizations may encounter, making it a valuable resource for ongoing strategic health checks.

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