207: The Signs Your Company Has a Strategy Problem...and Doesn't Even Know It | John Hillen

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. 

In this episode, 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 

Timestamps:  

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, The Strategy Dialogue, distills decades of experience into practical lessons for leaders at every level. Find out more at johnhillen.com or connect with John on LinkedIn. 

Resources & Mentions: 

• The Strategy Dialogue by John Hillen 
• John’s website: johnhillen.com 
• John Hillen on LinkedIn 
• Patrick Lencioni, author referenced and blurb contributor 
• StrengthsFinder tool mentioned 
• Clayton Christensen and his work on disruptive innovation 

Podcast Contact Information:  

Website: www.learnit.com 

Email: podcast@learnit.com 

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