Strategy and Techniques for Change Agents, Strategists and Innovators. A newsletter from the author of “Big Bet Leadership”, “The Amazon Way” and “Think Like Amazon” John Rossman. A substack newsletter with thousands of subscribers.
Play Chess, Not Checkers is a sharp, story-driven chapter that challenges leaders to stop thinking one move at a time—and start shaping the entire board. Drawing on iconic examples from Bill Gates, Steve Jobs, Amazon, and Microsoft’s reinvention under Satya Nadella, this chapter shows how the most successful Big Bets come from imagining multiple moves ahead, leveraging other people’s outcomes, and designing flywheel strategies that reshape ecosystems. Practical, provocative, and deeply relevant, this free chapter reveals how systems thinking, benchmarking, and disciplined learning can de-risk bold decisions and turn ambition into lasting advantage.