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

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

From Lead the Team (Top 2% of Podcasts) by Ben Fanning

July 5, 2026 · 44 min · Episode 453

About this episode

Olivia Nottebohm discusses the importance of speed and adaptability in leadership during technological shifts.

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…

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