#110—Sukhinder Singh Cassidy: Embracing Risk, Agility, and Resilience for Success

Feb 9, 2024

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Sukhinder Sing Cassidy is the leader of the growth and performance of Xero globally. With more than 25 years’ experience in Silicon Valley as a CEO, digital leader and board member, she has experienced building and scaling global companies including Google, Amazon, Yodlee, Joyus and StubHub. She currently serves on the board of publicly traded fintech, Upstart with previous experience serving on the boards of Ericsson, Trip Advisor, Urban Outfitters, Stitchfix and J.Crew.

Working across such a diverse, prominent portfolio of companies has given Sukhinder a unique counter-perspective on how leaders and business owners look at risk and reward. Her book, Choose Possibility: Take Risks and Thrive (Even When You Fail) sheds light and dives deep into what she’s learned in her extensive career as a leader in tech, where risk-taking and volatility is the norm.

In this discussion, we journey through the art of risk-taking and decision-making, with its intricate interplay of creating a portfolio of bets, understanding variability, and fostering an environment that embraces ambiguity and iteration.

In this episode, she shares:

The interrelation between possibility and decision-making, and how it’s too-often wrapped up in the “myth of the single choice,” as she calls it
How taking a big risk often starts with building and evaluating a portfolio of small possibilities—and how you build this
How, as a leader, you shouldn't force people to give you false precision—which often results in failures, plus three more mistakes leaders make that inhibit risk-taking and the exploring of possibilities
How the best risk-takers aren’t successful from an absence of fear, but rather, by learning to master what Sukhinder calls “the universal risk equation.”

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Episode Timeline:

00:00—Highlight from today's episode
1:14—Introducing Sukhinder + the topic of today’s episode
3:06—If you really know me, you know that...
4:10—What's your definition of strategy?
5:26—Why did you name your book, Choose Possibility?
6:53—What is the "risk of the single myth"?
10:18—What advice do you have for someone that realizes they're falling into the trap of narrowing on too few ideas?
12:00—How do you know if you have too few or too many ideas?
15:18—What are the first steps someone should take in pursuing new ideas?
16:48—How should leaders create a risk-taking environment?
19:36—Could you talk to us about the psychological impact of taking small bets?
21:59—What is "the universal risk equation"?
25:09—What can a company do at zero to maintain agility as they grow?

27:55—How can people follow you and continue learning from you?

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Additional Resources:

choosepossibility.com book
LinkedIn: https://www.linkedin.com/in/sukhinders
Twitter: https://twitter.com/sukhindersingh

Thank you to our guests, thank you to our executive producer, Karina Reyes, our editor, Zach Ness, and the rest of the team. If you like what you heard, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff. Thank you for listening.

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