What a Skydiving Hall of Famer Can Teach Leaders About Turning Risk Into Opportunity

The Future Of Work With Jacob Morgan

In business and in life, the most dangerous risk you can take is avoiding risk altogether. Whether it’s leading a team, making strategic investments, or navigating unpredictable markets, risk is always present, yet most leaders misunderstand how to harness it. In this episode, Jim McCormick, best-selling author (The First Time Manager, The Power of Risk) and founder of the Research Institute of Risk Intelligence, shares lessons from 5,590 skydives, high-stakes political decision-making, and years of advising executives on building “risk intelligent” organizations. He breaks down why people are naturally risk-averse, the two-part “Risk Equation” leaders must master, and how to balance instigators and mitigators for optimal decision-making. You’ll learn how to assess opportunities using ideal, most likely, and worst-case scenarios, implement “Possibility of Success Enhancement Measures” (POSSUMS) to improve outcomes, and set guardrails that encourage innovation without micromanagement. Jim also explores how to measure personal and team Risk Quotients, create cultures that reward constructive risk-taking—even when initiatives fail—and avoid the trap of over-relying on AI for critical decisions.

________________

Start your day with the world’s top leaders by joining thousands of others at Great Leadership on Substack. Just enter your email: ⁠⁠https://greatleadership.substack.com/