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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Most strategic plans look like extended budgets—but they lack one key ingredient: real choice.
In this insightful segment, Jay Holstine challenges CEOs to stop thinking like accountants and start leading like strategists. Drawing from Roger Martin’s Strategy Choice Cascade, Jay walks through five critical questions every CEO must answer to build a meaningful 2026 strategic plan—one that defines how you’ll win, not just what you’ll spend.
You’ll learn how to turn planning meetings into decision-making forums, identify your unique edge, and commit to bold choices that shape the future of your organization.
Key Takeaways:
The real difference between a plan and a strategy
How to apply the 5 questions from the Strategy Choice Cascade
Why great strategy is about saying no
Practical steps to align your leadership team before year-end
📌 For CEOs and executive teams ready to lead decisively in 2026.
📌 About Jay Holstine
Jay is a Vistage Chair and CEO coach based in Dallas–Fort Worth. Through his peer groups and executive coaching, he helps business leaders sharpen strategy, scale with purpose, and build resilient organizations.
📧 Learn more: jayholstine.com
9 episodes
