When Sukhinder Singh Cassidy, HBA ’92, returned to Western University this week, she had a simple message for new graduates: don't strive for perfection.
“The world doesn't need you to be perfect,” she said. “It needs you to be consistently imperfect to have the impact you're capable of having.”
The global technology leader, entrepreneur, and CEO of Xero addressed Faculty of Social Science graduates on June 11 after receiving an honorary Doctor of Laws degree. The honour recognizes a 30-year career that has taken her from Wall Street to Silicon Valley, where she has held leadership roles at Google, Amazon, and StubHub, founded multiple companies, and advocated for greater gender equity in technology and venture capital.
In her citation, Ivey Acting Dean Nicole Haggerty described Singh Cassidy as an extraordinary Ivey alum, a globally respected technology leader, and a passionate champion for gender equity and economic empowerment. Among other accomplishments, Singh Cassidy was the inaugural recipient of the Ivey Alumni Achievement Award in 2019, and more recently established the Ivey Women Investing in Leadership Case Competition, which supports the development of 50 new teaching cases focused on women's perspectives in business.
A “C player” with an A-plus career
Despite a resumé many would call exceptional, Singh Cassidy described herself to the graduates as “a C player.” She recalled being the student who once complained to a teacher about receiving a 99 per cent instead of 100, and who worked relentlessly for a perfect report card at Ivey. Then she graduated and, in her words, “hit the real world with a thud.”
Singh Cassidy said it took more than a year, more than 30 interviews, and a string of part-time jobs before she landed her dream offer at Merrill Lynch in New York.
“If life were a school exam, my job search success rate was only 6.6 per cent,” she said. “In academic terms, that's a spectacular and flaming F.”
That experience, she said, changed the way she thought about success.
“An A is not a grade on a single paper. It is the cumulative result of a high volume of high-effort attempts, many of which will fail,” she said.
Singh Cassidy pointed to her own career as evidence. She told graduates that one of the companies she co-founded failed, another had mixed results, and that she was ousted from her first CEO position after only six months. Yet those setbacks did not define her career. Instead, she said they became part of a larger portfolio of experiences that ultimately led to leadership roles at some of the world's most influential companies.
“In school, that's a C. In the real world, those individual As, Bs, Cs, Ds and Fs add up to what most would regard as a pretty successful career,” she said. “In the report card of life, a C is truly an A.”
Singh Cassidy also drew on examples outside of her own career. Elite financial traders, she noted, are right only 55 per cent of the time. Wayne Gretzky's career shooting percentage was 17 per cent. Even Women's National Basketball Association stars convert just 40 to 50 per cent of their shots, with superstars reaching around 60 per cent, she said, noting her involvement with the inaugural Toronto Tempo franchise.
“If these legends were graded by a professor, they'd be on academic probation,” she said. “But in reality, they've succeeded because they understand that cumulative success requires a big denominator of choices made, including choices that will fail a good portion of the time.”
Choosing possibility
Singh Cassidy distilled her philosophy, the subject of her Wall Street Journal bestselling book Choose Possibility: Take Risks and Thrive, into a four-part framework:
1. Pipeline – Don't hunt for one perfect path; pursue multiple possibilities in parallel;
2. Prepare to be lucky – Luck isn't magic; it's where “serendipity meets hard work”;
3. Pre-mortem failure – Before you act, imagine the failure and plan your next move; and,
4. Portfolio thinking – Treat your career as a collection of bets, not a single shot.
Choosing possibility, she said, is why she agreed to an informal conversation with Google when the company had fewer than 1,000 employees. That decision eventually led to her helping launch Google Maps and build Google's business across Asia Pacific and Latin America. It also influenced personal decisions, including saying yes to a blind date with fellow Ivey graduate Simon Cassidy, MBA ’94, whom she has been married to for more than 20 years.
A return to Ivey
Singh Cassidy's visit to Western also included a stop at Ivey the day before, where she led the HBA Class of 2026 Ivey Pledge Ceremony on June 10.
In a LinkedIn post following the event, she reflected on reciting the Pledge alongside graduates – a tradition that did not exist when she was an HBA student. She praised Ivey's commitment to responsible business leadership, noting the Pledge's emphasis on acting honourably, acknowledging mistakes openly, and making positive contributions to society.
“Thank you, Ivey, for making this the standard for your new grads to aspire to,” she wrote.
The following day, she left graduates with one final challenge: to be a C player.
“Take confidence. Know there's not a single golden choice, nor one golden path,” she said. “Go out there, start choosing. Build your portfolio of bets. Take enough shots to matter, both big and small. Put A-plus effort into every one. New grads, keep choosing possibility, and please, please aim for that C.”
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