Episode
Box COO: If Nothing Feels Broken, You're Moving Too Slowly | Olivia Nottebohm
- Published
- Jul 5, 2026
- Duration seconds
- 2610
- Processing state
not_requested- Canonical source
- http://www.benfanning.com/theceosessions/olivia-nottebohm-box
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Summary
AI is changing leadership faster than most executives can lead their team. In this episode of Lead the Team , Ben Fanning sits down with Olivia Nottebohm, COO of Box , to discuss why the companies that win technology shifts aren't the ones with the perfect strategy—they're the ones willing to move before they have all the answers. After helping scale Google Cloud, Dropbox, Notion, and now Box, Olivia shares the leadership frameworks she's used to navigate some of the biggest technology shifts of the last two decades. You'll learn: How to make faster decisions without having all the information. How to turn AI anxiety into optimism across your organization. What separates the companies that win technology shifts from the ones that get left behind. Why speed beats certainty during periods of massive change. How elite leaders build teams that thrive under pressure. Whether you're a CEO, executive, founder, or ambitious professional navigating leadership in the AI era, this episode will challenge the way you think about decision-making, organizational transformation, and leading through uncertainty. Chapters 00:00 – If Nothing Feels Broken, You're Moving Too Slowly 02:02 – The Biggest AI Mistake Leaders Are Making 03:59 – Why Speed Beats Certainty 07:54 – Reinventing Organizations for the AI Era 09:16 – Turning AI Anxiety into Optimism 14:16 – Why Data Strategy Determines AI Success 17:40 – Leading Teams Through High-Pressure Sprints 22:22 – The Culture Behind Elite Technology Companies 25:07 – Why Great Leaders Embrace Failure 30:11 – Turning Vision into Execution 33:36 – The Transition from Consultant to Operator 36:49 – Why Empathy Makes Leaders More Effective 42:51 – Olivia's Final Leadership Advice Ben Fanning interviews world-class executives, founders, and leadershi…