For business leaders, especially at relatively small companies, the idea of applying gen AI to strategic planning is mouthwatering. This article explores the potential and limits of AI in helping such companies chart their strategies. Through the lens of two disguised case studies the authors show how gen AI can help companies identify some challenges and opportunities that managers missed, overcoming the human biases, but by the same token missed some possibilities rooted in the company’s specific capabilities. And although gen AI was less able to imagine possible future scenarios because its forecasts were entirely rooted in historical data, clever promoting enabled it to surface issues and questions that human managers ignored. The authors conclude that knowing gen AI’s weaknesses allows managers to take advantage of its strengths. The key is to view gen AI as a tool that augments, rather than replaces, your strategic thinking and decision-making.