297: AI Leadership Strategy: Your 90-Day Blueprint for Winning with AI — with Charlene Li

Apr 21, 2026

Charlene Li, NYT bestselling author and disruption leadership expert who founded Altimeter Group, outlines practical AI leadership. She explains why AI should be tied to business strategy, the 18-month rolling roadmap, why pilots fail, speed as a moat, overcoming perfectionism (especially for women), becoming publicly AI-fluent, culture techniques like “how did you use AI?”, and the superhuman mix of AI plus human judgment.

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INSIGHT

AI Roadmap Serves Strategy Not Replaces It

You don't need a separate AI strategy; you need an AI roadmap that serves your existing business strategy.
Charlene Li describes a company whose seventh strategic objective was explicitly "use AI to accomplish the first six," illustrating AI as an enabler of mission goals.

ADVICE

Create An 18 Month Rolling AI Roadmap

Build an 18-month rolling AI roadmap with six quarterly goals showing how AI will deliver measurable value each quarter.
Write strategy in ink and the roadmap in pencil, review every quarter, revise the next five quarters and add a new one.

INSIGHT

Speed Is The New Competitive Moat

Speed is the new competitive moat in AI adoption; waiting for certainty cedes advantage.
Charlene Li calls out that leaders are waiting on the sidelines and must lay a 90-day foundation to run as fast as they can go.

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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!