Michael Lewis specializes in narratives about quirky individuals who zig when everyone else zags. In “Moneyball,” he tracked the astonishing success of Billy Beane, the general manager who turned the Oakland A’s from underdogs into championship contenders by relying on statistics rather than acquiring star players. His 2010 book “The Big Short” dissected how a handful of renegades foresaw the collapse of the housing market, while everyone else was pouring money into subprime mortgages.

Both books were best sellers that were adapted into major feature films. But they raised a nagging question that Mr. Lewis never fully confronted: Why do most people, from sports managers to bankers, so often overlook the data and make colossal errors based on gut instinct? Why aren’t people as data driven as Billy Beane?

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In his coming book, “The Undoing Project: A Friendship That Changed Our Minds,” which W.W. Norton & Company will release this December, Mr. Lewis finally tackles that question.