Three Lessons From Chatting About Strategy With ChatGPT
Can ChatGPT Help You Think Strategically? One Leader Put It to the Test — Here’s What Happened
“AI may not replace strategic thinkers, but it can challenge how we think — and that might be its greatest value.”
In a world where artificial intelligence is increasingly embedded in our day-to-day work, the question isn’t just what AI can do, but how it can help us think better. In this timely and provocative article from MIT Sloan Management Review, strategist and business leader Ben Shields shares his firsthand experience of engaging ChatGPT in a live conversation about strategy — and the three surprising lessons it taught him about the future of thinking, leadership, and competitive advantage.
This isn’t about AI writing reports or replacing consultants. It’s about how conversational AI can be a sounding board, a challenger, and even a thought partner when used the right way.
Three Key Lessons for Strategic Thinkers
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AI Makes You Slow Down and Clarify Your Thinking
Interacting with ChatGPT forces you to articulate assumptions clearly and structure your ideas more deliberately. It doesn’t replace strategic rigor — it sharpens it. -
AI Can Act as a Provocative Thought Partner
While it doesn’t replace human insight, ChatGPT can surface fresh perspectives, analogies, and provocative questions that help leaders escape their own echo chambers. -
Using AI for Strategy Requires the Right Framing
ChatGPT is not a crystal ball. It’s a tool that reflects the quality of the prompts it receives. When you guide it well, it can be remarkably insightful — but it won’t do the heavy lifting for you.
Why This Experiment Matters
This article goes far beyond theory. It’s a real-world demonstration of how AI is becoming part of the strategic conversation, not just the execution layer. In today’s high-stakes business environment, leaders need agility, clarity, and the ability to challenge assumptions in real time. AI, when used thoughtfully, can support that process.
It also raises important questions for modern strategists:
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What does it mean to collaborate with a machine?
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How can AI improve — rather than dilute — the human elements of judgment and creativity?
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Where should leaders draw the line between human intuition and algorithmic insight?
The Bottom Line: Strategy in the Age of AI Isn’t Solitary Work Anymore
As Ben Shields explains, AI doesn’t have to give you the answers to be useful — sometimes it helps simply by asking better questions. For business owners, executives, consultants, and strategists alike, this article is a compelling look at how to co-create smarter strategy by leveraging technology as a partner in thinking.
It’s not about replacing your strategic brain — it’s about upgrading it.
