The Learning Leader Show With Ryan Hawk - 432: Sukhinder Singh Cassidy - How To Take Risks & Thrive (Even When You Fail)

Duration: 59m
Broadcast on: 15 Aug 2021
Audio Format: other

Text LEARNERS to 44222 for more...

Full show notes at www. LearningLeader.com

Twitter/IG: @RyanHawk12 https://twitter.com/RyanHawk12

Sukhinder Singh Cassidy is a leading digital CEO and entrepreneur with more than 25 years of leadership experience founding, scaling, and advising companies including Google, Amazon, StubHub, Yodlee, and more. Most recently, Sukhinder served as the leader of StubHub, the premier global consumer ticketing marketplace for live entertainment, which she and her team sold for $4 billion in February 2020. Earlier in her career, Sukhinder built Google's business throughout Asia Pacific and Latin America.

Notes:

"Nothing will ever be attempted if all possible objections must first be overcome." - Samuel Johnson
- "We think when we do nothing there is no cost." That's not true. There's a cost to standing still.
Proximity to opportunity benefits us even more than planning. Sukhinder moved to Silicon Valley in 1997. She rode the tailwind of the Internet and being at the epicenter of it all.
- Prioritize the WHO before the WHAT.
As a leader, watch what you validate with your words and actions. Reward the behavior that you want. If you want to promote taking risks, then reward the people who do that. "You get what you create and what you allow."
At one point, Sukhinder went to her boss at Google (who worked with Eric Schmidt) and said, "I'm pregnant, I want to keep running international at Google. I need for you to pay for me and my nanny to travel the world business-class. And they said yes." BIG ASK.
- She did the calculus and realized it was a reasonable ask. And they said yes.
Career path - "My career is not linear, it's cyclical. It has ups and downs. I've made 13 different meaningful choices along the way."
The myth that there is a linear relationship between risk and reward. Not all choices have an equal amount of upside and downside...
Sukhinder sas been on the board of Urban Outfitters with Scott Galloway:
- Should you move to a big city? Should you move to your company's headquarters?
  - Being at the center of the action matters... It helps if you can understand the pulse of HQ
How to become a smart risk taker?
- What are our goals, passions, and values?
- What are we great at?
- Look for headwinds and tailwinds - (Join a growing company that has momentum)
  - With that said, Sukhinder went to StubHub and there were significant challenges
- Over-prioritize the WHO over the WHAT
Why did Sukhinder take the StubHub leadership role?
- It was a calculated risk
- She missed running a company of scale
  - They needed entrepreneurial and executive energy
How do you create an environment for people to take risks?
- You want people who are "truth-tellers, truth seekers, and authors"
- Make it safe to take risks -- Reward that behavior.
- Watch what you validate by your words and actions. Understand the magnitude and the weight of your words. People are always watching how the leader responds, who they commend, what they say...
How to go for a job that you aren't qualified for?
- "The next level of learning is going for something you don't know..."
- To be a CEO, you need depth AND breadth. You need to expand your skillset. This is the path to accelerated learning.
How do you know when you should leave a job?
- "I like 3-5 year sprints. Are you having fun? Are you making an impact? If you aren't having fun or making an impact, you'll want to leave."
- Think about: "Who am I doing this with? Are our values aligned?"
Why did Sukhinder want to be a CEO?
- "A little bit of ego"
- "I was built to lead"
- "I enjoy being on the hook"
People who sustain excellence:
- They surround themselves with other great people.
- They don't let their ego get in the way.
- They don't feel threatened by great people.
Career/Life Advice:
- "We tend to assume that everything is zero-sum. It's not. Choice is a multiplier of opportunity and we get to control it. Make a choice and get in motion."

I think you want to create an environment in which people can be truth tellers, truth seekers, and authors. Most people wake up every day wondering if their leaders really want them to speak up, do they really want them to ask questions, do they really want a debate in the conversation, do they really want a new idea to be presented and interrupt the flow of how the organization works, you have to create a construct in which people feel very comfortable doing those things. And I'd say the best way I noted you to do that as a leader is you have to make it safe in little ways. Welcome to The Learning Leaders Show presented by Insight Global. I am your host, Ryan Hawk. Thank you so much for being here. Text learners to 44222 to become part of Mindful Monday. You along with tens of thousands of other learning leaders from all over the world will receive a carefully curated email from me each Monday morning to help you start your week off right. You'll also receive details about how my book Welcome to Management will help you become a more effective leader. Text learners to 44222. Now on tonight's featured leader, a great one. It's Sikinder Singh Cassidy, an executive and entrepreneur with experience building, scaling, and leading businesses for more than 20 years including StubHub, Google, and Amazon. He's also the author of a great book titled Choose Possibility, Take Risk, and Thrive, Even When You Fail. A few of the topics we discuss, the myth that there is a linear relationship between risk and reward. Then why don't we have to be specifically qualified for a job before going for it. She tells some great stories about that one. Then how to build a culture that rewards smart risk taking. Ladies and gentlemen, you're going to love it. It's Sikinder Singh Cassidy. All right, Sikinder, I want to start at a specific moment in your career. And this may surprise you, but I know I've heard you talk about this on a stage before. So there was a time when you were working at Google and you walked into Eric Schmidt's office and you said, quote, "I'm pregnant, but I want to keep running our international business at Google. I need for you to pay for me and my nanny to travel the world business class." And they said, yes. And I love this story because it's a big ask, but you have to know at that point that you've earned it. Can you take us inside that room, what you were thinking, and how you had the guts to make that big ask? Sure. Well, first of all, I want to make sure the story is entirely accurate and sometimes get translated. I actually asked Omid Kortistani, my boss, who also talked to Eric, but Eric was aware. My boss was the chief business officer and obviously I had a lot of exposure Eric Schmidt, our CEO. He was kind of to do the endorsement for my book, but it was Eric and Omid. And Omid, I was who I asked and Eric was definitely aware and supportive. So it's going through my head at that moment. And many of you know this as we have the good fortune to you know, ascend in our careers if we do good work. Well, I've been married a year, I'm 24, I'm 34 years old, 35 years old, and I'm pregnant and I've just been in this job. I, you know, I came to Google to run local and maps and be the first kind of leader there, but I moved over to run international and my territories were from China all the way to Brazil. So we used to call that rest of world. And then I changed the name that Asia Pacific Latin America. So what's going through my mind is like, I don't want to give up this job. I mean, you're into this job, but like my god, like, I don't want to leave a baby at home. What am I going to do? And so you're right. I I could not think of a way to make it work that was good work for my family. And by the way, even then at home, I negotiate with my husband to be like, this woman asked for work, but that means that you have to be okay that we're disappearing for two, two and a half weeks at a time, I'm going to take our daughter with me, which he wasn't particularly happy about, but he supported it if I can get Google to say yes. And, and I went into that room, I would say trepidation, but I went into that room knowing two things. Number one, by the way, this is a huge ask to go in there and be arrogant about it would be a sin. I'm like, nobody needs to say yes to this. But at the same time, doing the calculus that I've been working hard, I think I'm well thought of, I realized that for me to switch out and quit the job is also really painful for Google because I'm just getting going here like we're a year into, you know, building this business. And so that calculus says like, what do I have to lose by asking? And again, I, I definitely give a lot

Transcription truncated.