Sukhinder Singh Cassidy is a prominent tech executive and entrepreneur, known for her leadership at StubHub and her work at Google and Amazon. In the conversation, she shares valuable insights on navigating job transitions effectively. Cassidy emphasizes the importance of proactive communication and leaving a positive legacy, urging listeners to stay fully engaged until their departure. She also discusses how family influences shape risk-taking in career choices and highlights the necessity of balancing personal goals with organizational needs during these changes.
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volunteer_activism ADVICE
Don't Leave Before You Leave
Stay fully engaged in your current role until your departure, even if you're excited about the next opportunity.
This protects your reputation and ensures lasting impact.
volunteer_activism ADVICE
Beware Lingering
Define a clear timeframe for your transition, balancing thoroughness and efficiency.
Avoid lingering too long, as it diminishes impact and wastes time.
question_answer ANECDOTE
A Bad Transition Example
Sukhinder Singh Cassidy recounts a negative experience with an assistant who left abruptly.
The assistant left a large amount of unfinished work, causing significant inconvenience.
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In 'Choose Possibility', Sukhinder Singh Cassidy offers a fresh perspective on risk-taking, drawing from her own experiences of navigating successes and setbacks in her career. The book challenges traditional risk aversion by advocating for proactive engagement with risks to unlock possibilities and build resilience. It provides actionable advice on career development, networking, and achieving work-life balance.
Radical Candor
Be a Kick-ass Boss Without Losing Your Humanity
Kim Scott
Radical Candor by Kim Scott offers a practical approach to management by emphasizing the importance of caring personally and challenging directly. The book argues that effective managers must find a balance between being empathetic and providing clear, honest feedback. Scott draws from her experiences at Google and Apple to provide actionable lessons on building strong relationships, giving feedback, and creating a collaborative work environment. The book introduces the concept of 'radical candor' as the sweet spot between obnoxious aggression and ruinous empathy, and provides tools and strategies for managers to implement this approach in their daily work[1][2][5].
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)
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