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Aim For Impact With Your Choices, Advises Founder Of TheBoardList Sukhinder Singh Cassidy


Sukhinder Singh Cassidy is a leading technology executive and entrepreneur, board member, and investor with over two decades of experience founding, scaling and advising top tech companies. Joining Amazon in 1998, co-founding Yodlee, then joining Google as President, Asia Pacific and Latin America in 2003, Sukhinder most recently served as president of StubHub, which she led to achieve a $4+ billion sale in 2020. She is also the Founder of theBoardList, which addresses representation gaps in tech industry corporate boards.

Sukhinder is also the author of Choose Possibility: How to Take Risks and Thrive (Even When You Fail). She shares her thoughts on the importance of having a healthy relationship with risk, navigating career curves, and how to position yourself for a board seat in our recent conversation.  This conversation is part of my series of conversations with female tech leaders.

Nancy Wang: You have an impressive career where you’ve started three companies, served as the CEO of two others, helped grow Google, and have served as a board member for brands including TripAdvisor, J. Crew, and StitchFix. You attribute your flourishing career to numerous small and large choices made over decades, rather than to a single large decision. What mental frameworks and values guide your decisions?

Sukhinder Singh Cassidy: People always assume that risk taking is about one mighty choice. When we put that pressure on ourselves, we may or may not make the perfect choice. That pressure often keeps people paralyzed.

In mapping my own career, I have kept choosing to choose, and aiming for impact. I took many risks that did not work out. I was the founder of a company in video commerce 10 years before the current video commerce rage that is going on; we were too early. I was the CEO of a startup that I joined and then left six months later. The compounding benefit of what I learn at each stage unlocks the value of the next choice. 

If you want to choose once, you are betting on luck. When you become a calculated choice maker and risk taker who thinks about the probabilities and aims for impact, you can realize that the result may or may not be what you originally imagined, as long as you’re able to have impact, you increase your agility, resilience and ability to make the next choice and have this sort of outsized career impact that cannot be measured at any single point in time. 

Another thing that has helped me particularly well in making choices in my career is what I call putting the who above the what. Often we’ve been trained to believe that following your passion is the risk to take. To that I say, passions change and interests change, but who you choose to work with has an outsized effect on what you will learn and what you’ll be able to contribute. 

Wang: I recently heard a speaker refer to the M-curve of women’s careers that is almost like the McDonald’s arch. You may see yourself ascending the career ladder, getting bigger and bigger roles and having a larger and larger scope. And suddenly, you might find yourself coming down that arch. How would you apply your framework to navigating M-curves?

Singh Cassidy: People tend to transpose on successful people’s careers a kind of linearity, because they just look at the peaks of someone’s career. I know people do that with me. In my new book, I make a point to show you all of the dips in my career, which are not obvious because nobody from the outside ever tells that story. More of us have M-curves than people acknowledge. 

There’s a difference  between a bad M-curve and a good M-curve. When I think about women specifically, they occur because women may exit their career to go do childcare or caregiving. With COVID, there’s even a bigger risk of that when women disproportionately have been shouldering the caregiving load. With this, I worry about the bias someone may face as they try to reenter the job world. If you’re in this position, before you make the decision that nothing is possible and you must exit, I suggest you go to work and ask for what might be possible. Can you ask for and gain the flexibility that allows you to stay in the world of work right now,  and not have some of the pains that women feel when they completely exit and re-enter? That’s not to say exiting and re-entering is an incorrect choice for your life. It’s just that sometimes when women hit that M-curve, it’s because they’re in some ways having to return to the world of work after taking a hiatus, and they don’t get all the credit that they should for the level of responsibility or title they had when they left, particularly if they left in the middle of their career. The bad kind of M-curve is where we face bias or discrimination in our opportunity set for the choices we make in order to accomplish many of the other things that are important in our lives. Sometimes we bear the repercussions of the risks of our choices unfairly as women. 

The good kind of M-curve is having that growth mindset. I’ve taken steps back in my career. Some may say I’ve taken “title hits” or other things in order to grow or learn to have impact. I left Google and I became a founder and CEO of a 10 person startup. I took a step back in terms of revenues, corporate responsibility, and pay. I’ve switched industries in order to learn. The returns compound over time when you step back and take a career risk to learn something new for more impact.

Wang: You and I are both passionate about tackling gender bias in the tech industry. You address this issue through theBoardList, which you founded to connect women to board opportunities. Many ambitious women have the goal of joining a board of directors, yet the path to these positions is not always clear. What advice would you give to those seeking this type of leadership position? What should someone do to get themselves board ready?

Singh Cassidy: The number one thing I say to people who are looking for boards is to establish that if you want to be in the boardroom, figure out what boardroom you want to be in. Also,  identify where you are a thought leader and on what topic. In what specialization, in what field and in what function, for what stage, for what industry would a CEO turn to you and ask for your thoughts and advice on something?  As a board member, you cannot just advise on how to execute something; you are needed to provide strategic insight to a CEO. This could be in any dimension; you may be an infrastructure specialist, cybersecurity specialist, or a FinTech specialist. You could be great at strategic communication. Any of those things could be your superpowers or value proposition.You also need to identify what type of CEO and for what type of company you want to serve. Nailing down the answers to those questions gives you confidence that you probably are board ready, and helps you identify board fit.

When you’re walking into your first board interview, they’re not looking for another operator to actually run a division. They are looking for someone to give them strategic advice and insight.  When someone asks you “why do you think you should be on this board?” be very clear on what you have to offer specifically. 

This interview has been edited and condensed. 

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