Box COO: If Nothing Feels Broken, You're Moving Too Slowly | Olivia Nottebohm

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.Chapters00:00 – If Nothing Feels Broken, You're Moving Too Slowly02:02 – The Biggest AI Mistake Leaders Are Making03:59 – Why Speed Beats Certainty07:54 – Reinventing Organizations for the AI Era09:16 – Turning AI Anxiety into Optimism14:16 – Why Data Strategy Determines AI Success17:40 – Leading Teams Through High-Pressure Sprints22:22 – The Culture Behind Elite Technology Companies25:07 – Why Great Leaders Embrace Failure30:11 – Turning Vision into Execution33:36 – The Transition from Consultant to Operator36:49 – Why Empathy Makes Leaders More Effective42:51 – Olivia's Final Leadership AdviceBen Fanning interviews world-class executives, founders, and leadership experts to uncover the real-world lessons shaping modern organizations. Topics include AI leadership, executive psychology, high-performance teams, decision-making, organizational transformation, communication, and leadership under pressure.Follow Lead the Team for weekly conversations designed to help you become the leader others want to follow.