Sukhinder Singh Cassidy Outthinkers Podcast

Embracing Risk, Agility, and Resilience for Success

Sukhinder Singh Cassidy is the leader of the growth and performance of Xero, a technology company that provides cloud-based accounting software for small businesses. With more than 25 years’ experience in Silicon Valley as a CEO, digital leader and board member, she has experienced building and scaling global companies including Google, Amazon, Yodlee, Joyus and StubHub. She currently serves on the board of publicly traded fintech, Upstart with previous experience serving on the boards of Ericsson, Trip Advisor, Urban Outfitters, Stitchfix and J.Crew.

Working across such a diverse portfolio of prominent companies has given her a unique counter-perspective on how leaders and business owners look at risk and reward. Her book, Choose Possibility: Take Risks and Thrive (Even When You Fail) sheds light on what she’s learned in her extensive career as a leader in tech, where risk-taking and volatility is the norm.

On the Outthinkers Podcast, she discussed the art of risk-taking and decision-making, with its intricate interplay of creating a portfolio of bets, understanding variability, and fostering an environment that embraces ambiguity and iteration.

Listen to the full episode here.

Navigating Risk and Possibility on the Path to Success

We often think of success as resulting from one bold move or idea. But in reality, achieving big goals requires making many incremental choices in the face of uncertainty. As Singh Cassidy lays out in her book, Choose Possibility, recognizing this truth can help leaders become more agile, resilient risk takers.

Choose Small Before Choosing Big

It’s tempting to wait for a single brilliant insight before taking action. But breakthrough moments are rare. More often, progress happens through testing many smaller ideas. As Singh Cassidy explains, “You set a big goal, then all the work begins. You’re just picking your way through smaller choices.”

This iterative approach takes some pressure off the need for perfection. You make a choice based on imperfect information, collect data on what works and doesn’t, then refine. Over time, these micro-experiments build confidence in bigger bets down the line. And repeatedly exercising your choosing muscles develops critical leadership skills.

Cultivate an Agile Mindset

Navigating uncertainty requires agility: the ability to nimbly change course based on new inputs. According to Singh Cassidy, agility and its cousin resilience are the biggest rewards of measured risk taking. While the immediate result of a given risk may succeed or fail, the longer-term payoff is greater adaptability.

Leaders can nurture organizational agility by avoiding asking for “false precision” and giving teams room to iterate. Ask your teams to provide ranges rather than point estimates. And make sure multiple diverse perspectives are represented to stress test ideas. Institutionalizing this mindset takes practice, but the long-term benefits are immense.

Master the Risk Equation

Behind every risk lies a mental tug-of-war between fear of failure and “FOMO”: fear of missing out on potential gains. As Singh Cassidy notes, for action to occur, FOMO must outweigh negative anticipatory emotions brought on by fear of failure.

That’s why clearly visualizing success helps tip the scales toward risk taking. But seasoned leaders also introspect on failure. Mentally simulating plans not panning out defuses some of the scary unknowns. And exploring prospective fallback options generates confidence in your ability to cope.

Taken together, visualized upside and pre-mortem downside shrink perceived risk and provide the courage needed to act decisively.

Portfolio Planning for Organizations

For enterprises, managing risk across a portfolio allows pursuing varied time horizons and potential outcomes. Singh Cassidy cites Google’s 70-20-10 framework:

  • 70% to core business
  • 20% to adjacent innovations
  • 10% to transformational bets

At Outthinker, we also recommend Valize’s SparcHub (, a tool to keep track of ideas, manage your opportunity portfolio, and record learnings.

Leaders shouldn’t expect or demand the same level of predictability from moonshots as sustaining innovations. Planning across this continuum provides the necessary room to experiment.


In the face of uncertainty, progress comes not from awaiting perfect certainty, but from repeatedly choosing among imperfect options. With an agile mindset, pre-mortem mentality, and portfolio approach, organizations can navigate risk with intelligence and flexibility on their way to success.

Listen to the full episode here.

Sukhinder Singh Cassidy quote

More Resources

Are you a chief strategy officer or strategy, innovation, or transformation executive interested in joining one of our networks? Click the button to apply below.

0 0 votes
Event Rating
Notify of
Inline Feedbacks
View all comments
We would love to hear your thoughts.x