Charlene Li joins Federico Ramallo for a special 100th-episode conversation on disruptive leadership, business transformation, and her upcoming book Winning with AI. Charlene shares how she “fell into” being an analyst and author—starting at Forrester in 1999 after stepping back from running businesses to focus on family—then building a career at the front edge of major tech disruptions: the internet, search, social media, and now generative AI.

They unpack why ChatGPT’s interface was a breakthrough that made AI accessible to anyone with a browser, and why adoption often comes down to how people interact with AI—whether through chat, voice, apps, dashboards, or embedded tools like CRMs. Charlene explains that “winning” with AI is not about using shiny tools or chasing ROI in the abstract; it’s about creating or extending competitive advantage based on each organization’s definition of success. Her key message: AI must serve the business strategy, not run alongside it.

Charlene outlines why she chose a 90-day plan: leaders need a clear starting point. The 90-day blueprint helps teams align AI to strategy, build momentum, and create a rolling 18-month roadmap—where strategy is “written in ink,” but plans are “written in pencil” and updated quarterly. She argues that when everyone has access to similar models and tools, speed becomes the moat—not just adopting AI quickly, but adapting the organization quickly.

A major theme is that digital transformation is never about the technology—it’s about people. Charlene compares building trust in AI to onboarding a new hire: train, evaluate, delegate, and add QA (including “AI checking AI”) based on your organization’s tolerance for risk. They also explore AI fluency, identity disruption as roles change, and how leaders can support teams through ongoing transformation without burning people out.

Charlene closes with practical advice: ignore hype by anchoring AI to your biggest goals and problems, learn by doing (and learning publicly), and lean into new ways of working—like “vibe coding”—that may democratize building tools while requiring “Goldilocks governance” to stay safe and fast.

About Charlene Li:

- https://winningwithaibook.com

- https://charleneli.com

About Federico Ramallo ✨👨‍💻🌎

🚀 Software Engineering Manager | 🛠 Founder of DensityLabs.io & PreVetted.ai | 🤝 Connecting 🇺🇸 U.S. teams with top nearshore 🌎 LATAM engineers

- 💼 https://www.linkedin.com/in/framallo/

- 🌐 https://densitylabs.io

- ✅ https://prevetted.ai

🎙 PreVetted Podcast 🎧📡

- 🎯 https://prevetted.ai/podcast

- 🐦 https://x.com/PrevettedPod

- 🔗 https://www.linkedin.com/company/prevetted-podcast

00:00 Introduction to Charlene Li and Her Work

01:30 Journey into Business Transformation and AI

02:54 The Impact of AI on Business Strategy

06:26 Defining Success with AI

10:53 Creating a 90-Day AI Roadmap

13:47 Speed as a Competitive Advantage

15:19 Transforming Organizations with AI

18:04 Connecting AI to Business Strategy

20:05 The Role of CEOs in AI Adoption

22:51 AI as a Collaborative Assistant

25:56 Building Trust in AI Decision-Making

29:36 The Future of Jobs in an AI World

30:52 Fostering AI Fluency in Teams

32:47 Navigating Identity Changes with AI

36:26 The Importance of Continuous Learning

38:05 Avoiding AI Hype and Focusing on Value

41:48 The Future of No-Code and Low-Code Solutions

44:54 Differentiation in an AI-Driven World