Playing it safe is often the riskiest career move. Sukhinder Singh Cassidy—current CEO of Xero, former president of StubHub, and founder of theBoardlist—shares why growth comes from taking calculated risks and building a personal “risk muscle” over time. Drawing on her leadership across Google, Amazon, and multiple startups, she explains how to evaluate opportunities not just by stability, but by learning velocity, scope, and long-term upside. Cassidy also challenges leaders to rethink how they hire and develop talent, emphasizing potential over pedigree and encouraging teams to step outside rigid career paths. For organizations facing constant change, her perspective reframes risk-taking as a discipline—not a gamble. Listen to explore how intentional risk can accelerate both individual careers and organizational performance.
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