Leadercast’s Sukhinder Singh Cassidy on Choosing Possibility

As one of the most well-respected female tech executives in Silicon Valley, Sukhinder Singh Cassidy is no stranger to risk-taking. With 25 years of experience founding and/or helping scale companies like StubHub, Google, Amazon and theBoardlist, Sukhinder believes leaders must intentionally and repeatedly choose to take risks if they want to grow themselves, their teams and their organizations. Leaders must be in a continuous act of choosing possibility—to seek potential and inspire others to join them as they venture into the unknown. 

“To not take any risks is the riskiest move,” says Sukhinder in an interview regarding her recently-released book, “Choose Possibility: Take Risks and Thrive (Even When You Fail).” The key is to be a calculated risk-taker: someone who may not know all the answers of what is to come but has done their research, anticipated obstacles and set goals. Calculated risk-takers take leaps of faith, but minimize risk as much as they can in achieving the possibilities that lay before them. Some possibilities fail, others succeed, but leaders will never get anywhere without taking some level of risk. 

At Leadercast 2022—The One Thing (happening live May 4 at Fifth Third Arena in Cincinnati, Ohio), Sukhinder will discuss possibility and the skill of calculated risk-taking that is required in great leadership. She shares the stage with nine fellow leaders, each discussing what they believe to be the one thing you need on your leadership journey. 

When we think of the most successful risk-takers in the world, we often focus on the one big and risky choice that led them to where they are now. What we don’t see is the journey of ups and downs, the failures and successes, and the series of little risks leaders take each and every day to reach their goals. Risk-taking is not easy. It is uncomfortable. It fills us with fear and uncertainty. But leaders must get comfortable with taking risks. Not simply the big, career-defining ones—known in Sukhinder’s book as the Myth of the Single Choice, which is the idea that one choice is going to make or break us. It is the little decisions that come our way daily that pave the way for better risk-taking and open the door to greater possibilities.

Do you have risk-taking prowess to discover what is possible? Moreover, are you fostering an environment as a leader where people feel safe to take risks? Are you cultivating a spirit of possibility? Join Sukhinder at Leadercast 2022—The One Thing, to learn about possibility and the skill of risk-taking that it requires. Come learn and grow in your leadership live on May 4 in Cincinnati, Ohio, or virtually at select locations around the globe


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Hayley Panagakis

Hayley Panagakis is a freelance writer, editor and content creator. Connect with her on LinkedIn and visit her website at hayleypanagakis.com to learn more about her services.

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