Winning with AI
A Conversation with Charlene Li
My friend and longtime collaborator Charlene Li has just published a really important book called "Winning with AI: The 90-Day Blueprint for Success (co-authored with Dr. Katia Walsh), and I couldn’t resist asking her a few questions. I think you’ll find her answers as energizing as I did. This is a very important topic for our rapidly changing times!
SBK: Your book makes a counterintuitive claim: That organizations don’t need an AI strategy; they need AI to serve their existing strategy. But if AI is as transformative as everyone says, doesn’t it reshape strategy itself? How do you hold those two ideas together?
CL: It’s a real tension, and I hold it by thinking about what never changes. The mission of an organization — why it exists, who it serves, what value it creates — that doesn’t change because of AI. What AI changes is your ability to execute on that mission faster, at greater scale, with more precision than was ever possible before. So when I talk to CEOs, I’m not asking them to rethink their purpose. I’m asking them to look at their top strategic priorities and ask: where is AI the accelerant? That reframing alone changes everything about how they approach implementation.
SBK: I’m fascinated by your concept of the “superhuman” — people who combine AI’s cognitive infrastructure with what’s irreducibly human: empathy, intuition, judgment, wisdom. Maslow would have recognized this. But developing those capacities takes time and inner work. How do you reconcile that with your argument that speed is the new competitive moat?
CL: What I’ve seen in the research — and in practice with leaders across industries — is that speed and wisdom aren’t actually in conflict. They’re in conflict only when leaders treat AI as a decision-maker rather than a thinking partner. The leaders who move fastest with the best outcomes are the ones who use AI to compress information-gathering so that their human judgment — which is irreplaceable — can operate on better inputs, faster. Jeff Maggioncalda at Coursera called this “cognitive bootstrapping”: he’d form his own perspective first, then use AI to pressure-test it, surface blind spots, and accelerate the vetting process. The judgment is still entirely his. The speed comes from how he gets there.
SBK: The human capacity for self-reflection — noticing patterns in yourself, choosing to change based on what matters to you — is something you can’t automate. And yet the AI conversation often centers on productivity and efficiency. Is there a deeper argument in your book about what’s at stake for human identity when we hand over cognitive tasks?
CL: Yes, and it’s the part I care most deeply about. There’s a real risk that organizations use AI purely to drive efficiency — which is fine as far as it goes — and miss the more profound opportunity: AI offloading routine cognitive work could free humans to be more human. More empathetic. More reflective. More creative. More purposeful. I call the people who realize that potential “superhumans” — not because they’re superhuman in some sci-fi sense, but because they’re finally able to express the full depth of what makes us human, which we couldn’t access when rote tasks cognitively depleted us. But it doesn’t happen automatically. Leaders have to choose to design for it. That’s the leadership question that’s most underasked right now.
SBK: What’s the one question you wish every leader reading your book would sit with before they start implementing?
CL: “What are you trying to accomplish — and for whom?” Not “what can AI do?” Not “what are our competitors doing?” Just: what is this organization actually here to do, and who does winning serve? Leaders who start there end up making much better decisions about where to deploy AI and how to measure success. The ones who start with the technology almost always get lost.
Charlene Li and Dr. Katia Walsh’s Winning with AI: The 90-Day Blueprint for Success is available now at winningwithaibook.com.