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Big Bet Leadership-Play Chess Not Checkers

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.

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BBL-Hyper

Step inside the strategic mindset of today’s most effective leaders with this free chapter of Big Bet Leadership. In Chapter 2: Play Chess, Not Checkers, authors John Rossman and Kevin McCaffrey challenge leaders to abandon short-term, reactive thinking and instead master the art of seeing multiple moves ahead.

Using vivid, real-world examples—from Bill Gates and Steve Jobs to Amazon’s flywheel and Microsoft’s modern reinvention—this chapter reveals how transformative leaders don’t just build products, they design ecosystems. You’ll learn why the biggest breakthroughs rarely come from isolated genius, and how leveraging other people’s outcomes, reverse engineering success, and systems thinking can dramatically de-risk bold strategic bets.

This free chapter of Big Bet Leadership introduces practical frameworks like competitive benchmarking, outcome-driven thinking, and flywheel strategy design—tools that help leaders navigate complexity, avoid cognitive traps, and accelerate innovation without reckless risk. Whether you’re leading digital transformation, setting high-stakes strategy, or looking to build a “learn-it-all” culture, this chapter offers clear insights you can apply immediately.

If you want to move beyond incremental improvements and start making smarter, more confident Big Bets, this free chapter is your next move.

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