An interview with Meg Whitman about the difference between leading a Fortune 500 company and a startup, how to decide what risks are worth taking, what she learned from politics, how to manage during a crisis, and her best career advice.

Welcome to the 86th episode of 5 Questions with Dan Schawbel. As your host, my goal is to curate the best advice from the world’s smartest and most interesting people by asking them just 5 questions.

This episodes guest:

My guest today is the CEO of Quibi, Meg Whitman. Born in Cold Spring Harbor, New York, Meg graduated high school in three years in the top ten of her class. She originally wanted to be a doctor but ended up studying math and science at Princeton University, but later changed paths after spending a summer selling magazine advertisements. Meg went on to obtain her MBA from Harvard Business School and starting her professional career at Proctor & Gamble. From there, she worked as a consultant at Bain & Company eventually becoming a Senior Vice President before leaving to become an executive at Disney, Stride Right, and Hasbro. From 1998 to 2008, Meg was the CEO of eBay growing the company from 30 employees and $4 million in revenue to more than 15,000 employees and $8 million in revenue. Then in 2009 she ran for Governor of California later dropping out in 2010. A year later, Meg went back into the corporate world as the CEO of HP before stepping down in 2017. Then in 2018, she became the CEO of Quibi, a short-form original mobile-only platform. I’ve wanted to speak with Meg for years because of her breadth of experience, both in politics and at different companies, has fascinated me.

The 5 questions I ask in this episode:

1. You’ve been the CEO of two Fortune 500 companies and are now the CEO of a startup. What do you find are the differences, similarities, opportunities, and obstacles between being a CEO at a large versus a small company and how did your prior positions prepare you for this new role?
2. You’re a believer in the importance of risk-taking and while you’ve received a lot of support for Quibi, most startups don’t succeed. How do you decide what risks are worth taking?
3. What did you learn from the experience of running for Governor of California that helped you become a better business leader and what did you learn from your business career that made you a better politician?
4. The workplace has changed so much since you started your career and is currently going through another transformation amidst the Covid-19 pandemic. What should leaders do to effectively manage their workforce during this crisis and how do you think the workplace will be transformed in the aftermath?
5. What is your best piece of career advice?

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