Using AI to Reach Tail Solutions

Welcome to episode #1021 of Thinking With Mitch Joel (formerly Six Pixels of Separation).

At a time when strategy is often confused with forecasting and certainty is mistaken for rigor, the work of Roger Martininsists on a more demanding discipline: making clear, integrated choices under uncertainty. Named the world's #1 management thinker by Thinkers50 in 2017, Roger is a writer, strategy advisor, and the former Dean at the Rotman School of Management at the University of Toronto, where he served for fifteen years and reshaped how management education engages with real-world complexity. Over decades, he has advised CEOs at companies including Procter & Gamble, Lego, Ford, American Express, Verizon, and Steelcase, helping leaders move beyond abstract ambition toward actionable, coherent strategies. His thinking has long been a personal touchstone for navigating difficult, high-stakes business problems, and he remains my go-to guide when confronting complexity that resists easy answers… a familiarity reinforced by his return here after previous appearances. Before academia, he spent thirteen years at Monitor, serving as co-head of the firm and grounding his thinking in the realities of corporate decision-making. His newly updated book, Playing To Win, Expanded With Bonus HBR Articles - How Strategy Really Works co-authored with A.G. Lafley, remains one of the most influential strategy texts of the modern era, distilling strategy into a set of five integrated choices about where to play and how to win, supported by capabilities and systems that reinforce those decisions. Across thirteen books and more than thirty Harvard Business Review articles, Roger has explored integrative thinking, democratic capitalism, governance and the design of business itself, consistently challenging leaders to resist false tradeoffs and simplistic answers. His work confronts contemporary issues head-on: the misuse of AI as an answer machine rather than a thinking partner, the hollowing out of education into ideological extremes, the erosion of institutional trust and the persistent illusion that the future must resemble the past. Through it all, his argument is steady and clear: strategy fundamentals endure, and superior managerial effectiveness begins with disciplined thinking, principled choice, and the courage to commit. If you're not following his free Substack, you reall should. It's always an honor to spend tie with Roger. Enjoy the conversation…

• Running time: 58:39.
• Hello from beautiful Montreal.
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• Here is my conversation with Roger Martin.
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• Playing To Win, Expanded With Bonus HBR Articles - How Strategy Really Works.
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Chapters:

(00:00) - Introduction to Roger Martin. (02:53) - The Evolution of AI in Strategy. (06:05) - AI as a Thought Partner vs. Answer Provider. (09:02) - The Role of Diversity in Decision Making. (11:49) - The Impact of Education on Polarization. (15:15) - The Misapplication of Science in Society. (18:09) - Navigating Truth in Business. (21:08) - The Experimentation Mindset in Business. (31:55) - The Flaws in Business Education. (34:37) - Philosophical Perspectives on Decision Making. (40:21) - The Impact of Macro Factors on Business. (49:20) - The Shift in Global Economic Power. (55:23) - Skepticism Towards Economic Predictions. (58:01) - Trust in the Health Profession.