Coaching For Leaders

Sukhinder Singh Cassidy: Choose Possibility Sukhinder Singh Cassidy is a leading technology executive and entrepreneur, board member, and investor with twenty-five years of experience founding and helping to scale companies, including Google, Amazon, and Yodlee. Most recently, she served as president of StubHub, which thrived under her leadership and sold in 2020 right before the pandemic for $4+ billion. She is the founder and chairman of the Boardlist and has been profiled in Fortune, Forbes, The Wall Street Journal, Business Week, and The New York Times, among others. She has been named one of Elle’s Power Women, one of the Most Creative People in Business by Fast Company, and one of the Top 100 People in the Valley by Business Insider. She is the author of Choose Possibility: Take Risks and Thrive (Even When You Fail)*. In this conversation, Sukhinder and I discuss how to handle a transition in a way that works for both you and the organization you’re leaving. We discuss the value of proactive communica