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 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.
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