Your AI may be too polite to save you. Mine was. I’d bring it an idea, and it would respond like a very expensive motivational poster: “Great direction.” “Strong potential.” “Very promising.” Lovely. Also mostly useless. Because what I needed was not validation. I needed resistance. The blind spot. The hidden risk. The banana peel on the product roadmap. So I built a practitioner framework for discovering unknown unknowns with AI. The core problem: AI models have two habits that quietly sabotage serious thinking. They are agreeable. They stay in the nearest conceptual neighborhood. Ask about legal AI, and you get contracts, clauses, redlines, compliance. Useful? Sometimes. Surprising? Rarely. The trick is not to type “be brutally honest.” That mostly gives you the same compliment sandwich with sharper mustard. The trick is to change the structure of the task: -> Make flattery invalid. -> Force disagreement. -> Ban the obvious domain. -> Ask for long-jump analogies. Then break the analogy before trusting it. In the article, I walk through the full framework using a fictional GenAI legal-product company — ClauseVanta — and show how AI can surface insights from depositions, medication adherence, airport security, nuclear control rooms, and even banana monoculture. Yes, bananas. Because sometimes the best product strategy insight is hiding in agriculture, wearing a yellow jacket. The article is about getting less “great idea” from AI… …and more “here is the thing that may quietly kill it.” Which, frankly, is what good thinking has always needed. Read the full article here: [linkedin.com/pulse/your-ai-t…] #AI #ProductStrategy