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Leadership

You Can Persist Through Tough Times by Reminding Yourself Everything Is Cyclical

Sukhinder Singh Cassidy has had a successful career in tech. Her latest venture makes it easier for corporate boards to bring more women to the table.
You Can Persist Through Tough Times by Reminding Yourself Everything Is Cyclical
Image credit: Courtesy of Sukhinder Singh Cassidy
- Entrepreneur Staff
Staff Writer. Covers media, tech, startups, culture and workplace trends.
11 min read

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In this series, Open Every DoorEntrepreneur staff writer Nina Zipkin shares her conversations with leaders about understanding what you have to offer, navigating the obstacles that will block your path, identifying opportunity and creating it for yourself and for others.

At the rate we’re going, women would achieve parity on corporate boards in more than 35 years, according to a recent study. As recently as last year, Fortune 500 boards were 79.8 percent male. But tech industry veteran Sukhinder Singh Cassidy wants to see a solution sooner.

In 2015, Cassidy launched theBoardList with the mission of creating a platform that would connect women leaders with board opportunities in the tech industry. With the support of 900 CEOs, senior executives and venture capitalists, to date, more than 1,400 senior women leaders have been nominated by their peers through theBoardlist to serve on private boards in the U.S., Europe and Canada.

Cassidy got her start at Amazon, co-founded financial services startup Yodlee and spent several years at Google overseeing the company’s Asia Pacific and Latin America operations. She then served as CEO of shopping platform Polyvore and founded another company, an ecommerce startup called Joyus. She is currently a board director at Ericsson and TripAdvisor.

With just a glance at Cassidy’s resume, it’s clear that she has had a successful career in Silicon Valley, but it wasn’t always smooth sailing. She has seen what is lost when there is not a diversity of voices at the table.

“I think there is a moment in time right now, where everybody recognizes the severity of the problem of gender parity -- not just inside of tech but outside it as well," Cassidy says. "For the first time in my lifetime, I'm seeing a number of different platforms and approaches that use technology to solve the problem. There are platforms around talent, around boards, around entrepreneurship, in seed funding for women [that] can accelerate the rate of change. That's an exciting thing to witness and be a part of.”

Entrepreneur spoke with Cassidy for more insights about the courage to know when to call it quits and why in business and in life, you need to keep in mind that everything is cyclical.

Related: Want to Achieve Big Goals? The First Step Is to Get Comfortable With Failure.

Why did you want to start theBoardlist?

The genesis of starting theBoardlist was frustration with the lack of solutions with regard to the problem of women in tech and gender parity. Several VCs had come to me and asked for my thoughts on how to help on diversity and tech. I had been brainstorming with one of them and come up with the idea of putting a woman on every series B board and beyond. I'd had that conversation as early as 2014 and I was fairly frustrated that it was a great idea and nothing happened with it. So a year later, I started theBoardlist and built it myself.

One of the biggest positives of theBoardlist is it invites men and women leaders to participate. It's not a shaming product. It says look, if you want to help, you can simply do so by nominating a great woman you know for a board. Here's something you can do in five to 10 minutes. It has resonated deeply with men and women business leaders -- no one says no to participating in theBoardlist.

Related: You Need to Meet Your Challenges With Pathological Optimism at Every Turn

What are some of the challenges theBoardlist has faced in getting up and running?

The number one biggest challenge we still face is that most early stage founders don't prioritize putting an independent on their board, because they're just too busy. Even though it could really help them grow the company. The second obstacle -- and I think we're seeing the result of that today in situations like Uber -- is historically, private companies don't value corporate governance. It seems like overhead.

We only ever see the negative side of corporate governance, when something goes deeply wrong and [then the question is] why didn't the board know? Or shouldn't the board have been more involved?

But as a culture, I think we have long valued innovation and creativity, which is awesome. But with entrepreneurs, we tend to place less emphasis on management and governance and best practices. When it doesn’t work out, that’s when everyone talks about corporate governance. We don’t really embrace it as an opportunity. [For founders], instead of thinking about all the downsides of the board, think about it as an opportunity, way before a crisis [hits].

Related: Why Entrepreneurs Should Question Everything and Everyone, Even the Experts

In 2016, Fortune 500 company boards were 79.8 percent male. What innovation do we miss out on when just one type of person is shaping these conversations and the directions of these companies?

Even before we talk about adding a woman, let's just talk about adding diversity of thought. There is a cost of missing diversity. One of the first risks of missing diversity in your board is missing key trends, digital being the most disruptive of them all. You have no perspective outside of financial investors on what's going on in the world and outside of your own four walls.

When you add the lens of gender, two additional things become clear. Number one, you're missing the voice of your customer. It's very fair to say that one of the big risks of missing diversity is not having a voice of the customer in the room, which is shocking. Women make most of the buying decisions in B2C companies. But we can also argue that many B2B to be companies also target women as a potential customer.

The risk is high and it is accelerating because most businesses are changing at an accelerated rate -- either with regard to who their customer is or who their next generation customer is. And at a minimum [they are] changing with technology trends.

Related: The Surest Way to Build Your Confidence Is by Not Fearing Change

Can you talk about a moment in your career that you had to advocate for yourself? How did you approach it?

The first time I was up for promotion to president [at Google], I didn't get it. And part of the reason I didn't get it was because of my philosophy, which is if you just put your head down and if you're really great at your job, that's enough. One of my key lessons was, that holds you pretty well up until the junior and midpoint of your career. And at some point you learn that if you're not heads up and attuned to the agenda of other people around you, their perceptions of you and their understanding of what you do, it can become a barrier to your career. And in the case of me moving to president, it was clear that although I was good at my job, there were some people on the executive staff who weren't aware of what I was doing or had questions [about my approach].

When I found out I didn't make president, I actually spent the next several months really embracing the people I knew had questions about my business. I went out of my way to create relationships with them and to give them visibility into what I was doing. The next time I came up for president, their concerns had been satisfied. And I got the promotion. But that didn't just naturally happen. You realize at a certain point in your career, if you want to keep progressing you do need to become attuned to everyone around you much more proactively and learn to embrace these different stakeholders -- whether or not they actually influence your day-to-day job or not.

Related: You Must Ask Yourself This Question Before You Pitch Your Idea

What was a mistake you made and how did you move forward from it?

When you look back on your biggest mistakes, they're often hiring mistakes and firing mistakes. Nobody says, gosh my mistake was hiring the right person. Most often people say almost all of the things I regret are people decisions. When I look back, it was often the case where it wasn't a competency [issue], but a culture fit. And I let that situation stand too long. I'd say over the years I've tried to make those decisions quicker. Because there is never a good outcome when you wait too long.

I think if you are any kind of empathetic leader, your first thought is well maybe this will work out. So I would just say the other challenge -- and it's an ongoing one -- is to have the courage when something's not working to call it sooner. I think that does take a lot of courage, particularly when you're attached to the person or the outcome.

Related: After a Decade in Business, This Founder Became CEO. Here is How She Tackles New Challenges With Conviction.

Over the course of your career, how have you grown and changed as a leader?

I would generally call myself an impatient person and that probably hasn't changed. But what has changed is early in my career, I fundamentally felt like I could orchestrate any outcome, like I was in control of my destiny, 100 percent [of the time].

I really feel like over the course of the past 20 years I've actually learned that the leadership mantra I should be following -- and I try my best to follow it -- is in fact you're not in control of the outcome. You're only in control of the input.

How has understanding that about yourself changed the way you view success and failure?

I put six years into Joyus. I can't tell you the number of times we had to make magic happen for the company to continue. Joyus is going through a sale process right now. I would say in my wildest dreams I didn't expect that outcome. I thought I'd be able to take it all the way through sheer will.

And the converse was, I started theBoardlist as a side project, never anticipating or thinking about how fast it would grow and how much traction it would have. We sit here today and Joyus won't be an independent company, which is everything I was sure it would be.

But theBoardlist was a side project that we're now pursuing seed funding for. I just never thought it would get there. I thought of it as a completely not-for-profit idea and [it] turns out that it is both economically viable and a great mission-driven company. Those two outcomes are totally reversed. I would never expected that.

In the case theBoardlist, I didn't put any expectations on it and it surpassed them all. You control so much and ultimately feel like you know you have ultimate control over the output. [But that] is a perspective that leads you to get personally attached to every outcome, including your ego and your sense of self -- as opposed to feeling like you just are doing the best you can. Sometimes it doesn't work out, but sometimes it does. And you're going to survive in either case.

Related: Why You Have the Wrong Idea About Who Is a Great Mentor

What do you say to yourself during tough moments?

I say persist, just hang on. The other thing I say to myself is everything is cyclical. I remember when I graduated, I went through a very tough time. My friends got in great jobs and thrived and it took me almost a year and a half to get my dream job. I was very self-questioning during that period. And then you know, things reversed and I was flying high and other people had tough times.

Nothing good ever lasts indefinitely and you're not nearly as good as you think you are when times are great. So persist, hang on.

What does entrepreneurship mean to you?

Possibility. I don't know if I'm going to start another company. But I have a bunch of ideas in a notebook. I enjoy thinking about the possibility even if I don't enact it. I've got one idea in particular that I think is kind of fun. I've been I've been chatting with my daughter about it because she would be the target customer. I don't know if we'll ever build it. But I feel pretty strongly that if you have an idea, all it takes to make it happen is you starting to iterate. If you [can] imagine it then you can create it.

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