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Release Date: Aug 26

When was the last time you worked ON your business, not just IN it? In this eye-opening episode, host Damon Lembi welcomes Dr. John Hillen—former U.S. Assistant Secretary of State, multi-time CEO, board chairman, and award-winning strategy professor—to break down what strategic thinking actually means for today’s leaders. Drawing from his hot new book, The Strategy Dialogue, John argues that strategy isn’t just for Fortune 500 boardrooms; it’s a muscle every leader can—and must—develop, regardless of company size. From unearthing the difference between “strategic planning” and “strategic thinking” to practical ways to shift your mindset, this episode is packed with actionable frameworks, real-world case studies, and wisdom to help you stop reacting and start leading.

If you’ve ever felt too busy to look beyond your to-do list, you’ll learn why only 4% of leaders naturally think strategically—and how to join them. Plus: stories from the Berlin Wall, lessons from the rise of Netflix, the fall of Blockbuster, and what grocery stores can teach you about your true strengths. Whether you’re an entrepreneur, executive, or aspiring strategist, this episode will change the way you see your business, your role, and your future.

What You’ll Learn:

• What separates strategic leaders from busy taskmasters (and why ownership of strategy can’t be delegated)
• Why “strategic thinking” is not the same as “strategic planning,” and how to make it a daily habit
• The 4% mindset: How truly strategic leaders map the ecosystem, spot patterns, and connect the dots long-term
• Real-life case studies: Why Netflix disrupted Blockbuster, and how Trader Joe’s and Whole Foods each leverage hidden strengths
• How to identify your company’s core competency (hint: ask your customers, not your marketing team)
• Tools and frameworks—from SWOT and “TOES” to actionable, Socratic dialogues—for thinking and leading strategically in any environment

In This Episode:

• 00:00 – The “strategic muscle”: why leaders must work ON the business
• 00:30 – Damon introduces John Hillen & today’s episode
• 01:26 – Why strategy is the heart of leadership
• 02:49 – Common excuses leaders use to avoid strategic thinking
• 04:51 – Only 4% of executives think strategically (and what the other 96% do instead)
• 07:36 – John’s background: Berlin Wall, Desert Storm, and the roots of strategic thinking
• 12:14 – How global experience shapes perspective and context
• 14:24 – Why John wrote The Strategy Dialogue & teaching strategy through dialogue
• 19:14 – Strategic thinking vs. strategic planning: Key differences
• 23:36 – Using “scenario planning” and creativity in traditionally rigid industries
• 24:51 – The essential mindset shift: think forward, ask better questions
• 26:26 – Why companies like Blockbuster and Kodak get disrupted
• 30:28 – Netflix’s three business model pivots: lessons in strategic agility
• 32:35 – How to get honest about your true strengths—ask your customers
• 35:49 – Whole Foods vs. Trader Joe’s: Different strengths, different strategies
• 37:21 – Beyond SWOT: the TOES framework for action-oriented strategy
• 44:40 – Can AI help with strategic thinking? The human judgment difference
• 47:00 – Why “how you think” is more important than “what you decide”
• 51:24 – How often should you revisit your strategy?
• 58:40 – Strategy, clarity, transparency, and public policy examples
• 1:00:10 – John’s final advice: Work on your business, not just in it

About Dr. John Hillen:

Dr. John Hillen is an award-winning strategy professor, best-selling author, and sought-after business leader with a career spanning the military, government, academia, and boardrooms. A former U.S. Assistant Secretary of State and CEO of multiple companies, John has taught leadership and strategy at Duke, George Mason, and other top universities. His latest book, , distills decades of experience into practical lessons for leaders at every level.

Resources Referenced:

• John’s website:
• , author referenced and blurb contributor
• tool mentioned
• and his work on disruptive innovation

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