Tech CEO Sukhinder Singh Cassidy: ‘Study Failure To Decrease It’

Failure is daunting—which is why Sukhinder Singh Cassidy studies it. The CEO of global accounting software company Xero knows if she can understand a plan’s possible downsides, she can create value for her team. She can actually diminish worry and increase involvement. Because when the fear of missing out is greater than the fear of failure, she says, people move.

All sides of an idea matter, Sukhinder says on this week’s episode of Corporate Competitor Podcast, which is why she directs her team to “pre-mortem” any potential failures. That way if anything goes wrong, everyone will be prepared.

“Most failures are not catastrophic,” says Sukhinder. “You can think through what you would do if these failures came to pass.”

Of course, fortune favors the prepared. But it also favors those teams with excellent chemistry. Sukhinder has learned this over the years, too. She knows that the people she works with matter more than any given role. 

The idea crystalized early in her career while working at Merrill Lynch. She wanted to be in the media and entertainment side of the company, she says, but she was placed in a different role. That changed everything for her.

Henry Michaels, the leader she worked for in the financial institutions department, ended up investing in her and accelerating her growth exponentially. The insight showed Sukhinder that the right person can turn an unglamorous assignment into a defining opportunity.

“The magical combination is finding somebody whose values you share,” she says. “[Hopefully] I look at them and I’m like, man, that person has a few things I can learn, too!”

Sukhinder talks about all this and more on the podcast, including:

• Find your purpose. Sukhinder rejects the idea that vocation, purpose and livelihood live in separate buckets. For her, they can all come together in one happy collective.

• Model imperfection. The CEO believes one of the biggest barriers to risk taking is the idea that leaders should always appear polished, certain. So, Sukhinder incorporates mistakes in how she plans the future. “I would rather model imperfection than model perfection,” she says.

• Small is powerful. Sometimes grand gestures win the day. Other times, it’s all about the small moments. Sukhinder remembers telling people about hiking the Great Wall of China while nearly six months pregnant. To her, it was a small travel detail. To others, it’s become mythology.