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FranklinCovey On Leadership

Sukhinder Singh Cassidy: Stop Playing It Safe With Your Career

FranklinCovey On Leadership

FranklinCovey

Business, Management

4.6 • 215 Ratings

🗓️ 17 March 2026

⏱️ 39 minutes

🧾️ Download transcript

Summary

Playing it safe is often the riskiest career move. Sukhinder Singh Cassidy—current CEO of Xero, former president of StubHub, and founder of theBoardlist—shares why growth comes from taking calculated risks and building a personal “risk muscle” over time. Drawing on her leadership across Google, Amazon, and multiple startups, she explains how to evaluate opportunities not just by stability, but by learning velocity, scope, and long-term upside. Cassidy also challenges leaders to rethink how they hire and develop talent, emphasizing potential over pedigree and encouraging teams to step outside rigid career paths. For organizations facing constant change, her perspective reframes risk-taking as a discipline—not a gamble. Listen to explore how intentional risk can accelerate both individual careers and organizational performance. FranklinCovey’s world-class learning solutions—delivered Live-Online, On Demand, or Live In-Person—are designed to build exceptional leadership skills and enrich your culture at every level of your organization. To learn more, email us at info@franklincovey.com, visit franklincovey.com, or call us at: 1-888-868-1776

Transcript

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0:00.0

I think that your job as a CEO is to be a realistic optimist.

0:05.7

It's like it's not to be, I think it is true, like people want to, people want clarity.

0:13.8

Even though people say they like ambiguity, lots of people don't like lots of uncertainty.

0:18.8

So they're looking for, it's like all of it. And it's,

0:22.2

and it's sometimes hard. They're looking for authenticity, transparency, yet a reason to believe,

0:27.3

right? Clarity. If the future is very uncertain, what is certain? Does that make sense? Certainty

0:33.6

with that uncertainty. So I think it's a CEO. I think your job is to sort of take all of that and say,

0:39.9

okay, well, how can I acknowledge what's ambiguous, yet give people clarity on the things that

0:45.4

need to be true for us to be successful and a path or confidence that you can get there, even

0:52.1

if the path is hard.

0:57.6

Hello. confidence that you can get there, even if the path is hard. Hello and welcome to Franklin Covey on leadership. I'm your host, Will Hodling.

1:02.3

Today's guest is Sue Kenderson Cassidy, the CEO of Zero, a global platform that helps

1:07.6

small businesses and their advisors run accounting and increasingly payroll and payments in the cloud.

1:13.5

So Kenderson Kasky is at a fascinating career. Before Zero, she co-founded the FinTech Pioneer Yodley. She helped scale Google internationally and later led teams at companies like Stubh, where she served as CEO.

1:26.3

She's also an entrepreneur and author of Choose Possibility,

1:29.9

where she explores how leaders build the habit of taking smart risks when the path isn't obvious.

1:35.8

In today's conversation, we'll discuss the business she's building at zero,

1:39.7

her leadership lessons across her diverse and varied career,

1:43.6

and we'll also dive into her personal experience as a mother and Canadian and a global company.

1:48.1

Sue Kinder, welcome to Frank and Covey on Leadership.

1:50.3

Thank you for having me.

1:52.2

Wonderful. I'm very excited for today's conversation.

...

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