EP335 - Kevin Ertell The Strategy Trap

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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 strategies and actionable advice for leaders looking to strengthen their execution capabilities. Kevin offers insights on leveraging constraints creatively, encouraging listeners to view limitations as opportunities for innovation, much like how companies like Costco manage to maintain low prices while driving efficiency.

As the discussion unfolds, the trio delves into the nuanced nature of workplace culture, highlighting the benefits of psychological safety, the impact of social incentives, and the importance of regular communication channels to keep everyone aligned within the execution framework.

Moreover, they touch on fascinating concepts such as pre-mortems, a proactive method of anticipating potential failures before launching a project, differentiating it from the traditional post-mortem analysis. This mindset shift encourages teams to address concerns upfront, minimizing the likelihood of catastrophic missteps in execution.

As the episode wraps up, Kevin shares his hopes for the book's impact, inviting listeners to access "The Strategy Trap" at their local bookstores or online. He emphasizes the vital interplay between strategy and execution, urging leaders to recognize that a well-crafted strategy is only as strong as its execution plan.

Join us for this enlightening discussion filled with practical lessons, captivating anecdotes, and a wealth of insights from an industry veteran. Tune in, and let's embrace better execution practices for a thriving business landscape!

Episode 335 of the Jason & Scot Show was recorded on Friday, October 10th, 2025

Join your hosts Jason "Retailgeek" Goldberg, Chief Commerce Strategy Officer at Publicis, and Scot Wingo, CEO of ReFiBuy and Co-Founder of ChannelAdvisor as they discuss the latest news and trends in the world of e-commerce and digital shopper marketing.