Winning With AI With Charlene Li – This Week’s Thinking With Mitch Joel Conversation

Episode #1041 of Thinking With Mitch Joel is now live.

This conversation with Charlene Li gets into one of the biggest gaps inside most organizations right now: everyone knows AI matters, but far fewer leaders know what to actually do about it. The noise is everywhere. New tools… new models… new headlines. New pressure from boards, teams, competitors and customers. But turning all of that into a coherent business response is a very different challenge. Charlene has spent her career helping leaders understand transformative change before it becomes obvious. She is a New York Times bestselling author, advisor to CEOs and boards, and someone many people first came to know through books like Groundswell, Open Leadership and The Disruption Mindset. Her latest book, Winning With AI – The 90-Day Blueprint For Success, co-authored with Dr. Katia Walsh, is not another book about what AI is. It is about what leaders should do next. What makes Charlene’s perspective especially useful is that she does not treat AI as a technology project. In fact, one of the strongest ideas in our conversation is that most organizations do not need an “AI strategy” as much as they need to understand how AI serves the business strategy they already claim to have. That shift matters. Otherwise, AI becomes another pilot, another experiment, another internal sandbox that makes everyone feel busy while very little value gets created.

Charlene pushes hard against that.

She argues that leadership teams need to move beyond scattered experimentation and start building real AI roadmaps tied to value creation and customer impact. Not vague transformation theatre. Not executive cosplay. Real choices. Real ownership. Real momentum. In our conversation, we talk about why AI adoption feels so lumpy inside organizations, why pilots may be the wrong model, why HR needs a seat at the table, and why efficiency is only the first and least imaginative use case. We also get into the human layer of AI: anxiety, identity, reskilling, trust, leadership and the possibility that AI could help create more human-centered organizations if leaders are willing to rethink how work actually gets done. Mostly, this is a conversation about responsibility. AI will not magically transform a company because someone bought the right tool. It changes things when leaders understand the work, the people, the strategy and the value they are trying to create.

Listen to my conversation with Charlene Li here: Winning With AI With Charlene Li – TWMJ #1041.

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