Xero CEO Sukhinder Singh Cassidy Says: When FOMO Fear of Failure, You Move

Sukhinder Singh Cassidy, CEO of Xero, reveals that her leadership philosophy was forged not in boardrooms but on tennis courts and in the high-pressure world of business development. She argues that the most powerful career decisions aren’t driven by titles or industries, but by the 'who'—the people you work with. Her core insight? When your fear of missing out (FOMO) exceeds your fear of failure, you take action. To shrink that fear, she advocates for 'pre-morteming' failure: systematically listing every possible downside of a decision so it loses its power. This mindset, honed through personal experience and tested in brutal moments like laying off 800 employees at Xero, led to a profitable turnaround. She also champions storytelling not as grand narratives, but as simple, repeatable moments—like hiking the Great Wall of China while pregnant—that build trust and culture. Her leadership is defined by radical transparency, imperfection, and the belief that 'winning ugly'—doing the hard, unglamorous work—is the only sustainable path to success.