9The Siren Song of Certainty

George had set himself up for a fall. He was the newly promoted chief strategy officer for a $4 billion global financial technology company. A brilliant analyst, his well‐earned reputation as the smartest person at the table had powered him up the corporate ladder. But having reached the C‐suite, George now felt pressure to justify his position. He knew that the CEO, Jack, admired self‐confidence and strong conviction in his leaders, and George made a point of displaying those qualities to remain in Jack's good graces.

As part of an ambitious strategy to reach $7 billion in revenue in two years, George placed nine‐figure bets on acquisitions in 2019. He expected one key addition, based in Shanghai, to open a $3 billion–plus market for the company's products. Based on what had worked in the firm's previous expansion in South Korea, he was certain of how the newly acquired firm should approach the major financial institutions in China.

The first six months didn't go as planned. The newly acquired operation struggled to gain traction, and its leaders were reluctant to enact some of George's recommendations. George attributed the difficulty to the competence of those local leaders, not to the strategy he had assuredly pushed. He raised his concerns and strongly encouraged the executive who oversaw Asia to replace members of the team. When Jack questioned George on these matters, George insisted that his analysis and strategic approach were correct, ...

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