If your organization is running AI pilots that aren't moving the needle, waiting for the right moment to commit, or treating AI as a technology problem for IT to solve — this episode is the reset you need.
Charlene Li, NYT bestselling author and one of the world's leading voices on disruptive leadership, joins Toni for her second appearance on Leading Women in Tech. When she was last on the show in Episode 225 (Run To Disruption), the AI conversation was just beginning to accelerate. Now, with her new book Winning with AI: The 90-Day Blueprint for Success freshly published, Charlene brings a framework that is both more urgent and more practical than anything most organisations are currently working with.
This is a conversation about AI leadership strategy — not as a technology decision, but as a leadership and strategic imperative. And it has particular resonance for women in tech, who face a specific version of this challenge: the deeply conditioned pressure to be certain before acting, and what that costs us when the window for leadership is open right now.
What we cover in this episode:
⏹ Why you don't need an AI strategy — you need an AI roadmap that serves your existing business strategy
⏹ The 95% pilot failure rate, and what to do instead of running pilots
⏹ The 18-month rolling AI roadmap: how to write strategy in ink and your roadmap in pencil
⏹ Speed as the new competitive moat — and what that means for leaders who wait for certainty before acting
⏹ The specific challenge women face: perfectionism, scrutiny, and the risk of sitting out the AI transition
⏹ What AI fluency actually looks like — and why becoming fluent publicly is a leadership act, not a vulnerability
⏹ The "how did you use AI to prepare for this meeting?" technique — and why it changes team culture fast
⏹ The superhuman thesis: what happens when uniquely human skills (empathy, judgment, wisdom, intuition) meet AI capability
⏹ Why the good people have to show up — and why women's voices are non-negotiable in shaping how AI is used
Connect with Charlene — today's guest and sponsor:
⏹ Website: charleneli.com
⏹ LinkedIn: linkedin.com/in/charleneli
⏹ Book: winningwithaibook.com
Mentioned in this episode:
⏹ Episode 225 — Run To Disruption with Charlene Li: tonicollis.com/leading-women-tech/225-run-to-disruption-charlene-li
Connect with Toni:
⏹ tonicollis.com
⏹ tonicollis.com/lets-chat
This episode was sponsored by our guest, Charlene Li. Thank you Charlene for helping to bring Leading Women in Tech to this community!
