Lessons of Risk-Taking from Family Influences

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 communication and clear timelines — plus some of the hidden costs of transitioning poorly. Finally, we made the invitation to consider transitions in the context of your long-term career goals. Key Points Don’t leave before you leave. Putting in maximum effort until you’re gone protects your reputation and the impact you’ve worked to achieve. Beware the cost of lingering. You likely know the right timeframe for your departure — use that to frame your transition. Leave opportunity in your wake. Use remaining time to set the team up for success, provide coaching and mentoring, and make it an easier transition for others. Tie up loose ends before you depart. Leave the team an organization in a place you would want to inherit if you were the new leader coming in. Take small steps, middle steps, and big steps. Avoid fixating on the myth of the single choice. Careers come together with many choices, over time. Resources Mentioned Choose Possibility: Take Risks and Thrive (Even When You Fail)* by Sukhinder Singh Cassidy Related Episodes How to Challenge Directly and Care Personally, with Kim Scott (episode 302) The Way to Make Better Decisions, with Annie Duke (episode 499) Making the Case for Your Promotion, with May Busch (episode 526) Discover More Activate your free membership for full access to the entire library of interviews since 2011, searchable by topic.