Jim Olson has spent his career helping businesses navigate moments of intense pressure from corporate crises to deeply personal challenges, running comms at United Airlines and Starbucks. In this episode, the author of Tailwind shares the lessons he’s learned from leadership, resilience, and facing adversity head-on.
Drawing inspiration from Captain Sully’s Hudson River landing, Jim explains why the best crisis leaders follow the same process: aviate, navigate, communicate. We discuss where crisis management often goes wrong, what leaders can learn from failures like United Airlines, and why “black box thinking” matters in both business and marketing.
Jim also opens up about his own cancer diagnosis and the mindset that helped him through it.
00:00 - Start 01:11 - Lessons from Captain Sully’s Hudson River landing 06:11 - The black box thinking approach to marketing 07:30 - Other crises Jim has had to deal with in his career 09:18 - When crisis management goes wrong - United Airlines 13:11 - Managing merging two cultures 15:27 - The situation when Jim’s CEO had a heart attack 18:00 - Jim’s cancer diagnosis 23:30 - The power of positive mentality 28:30 - Don’t ask yourself what if, ask yourself why not 31:34 - The power of a fourth space 34:05 - Crisis doesn’t build character, it reveals it 37:02 - Leadership lessons from Howard Schultz 38:58 - Jim’s advice for those people facing a crisis
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