Leaders are often trapped "inside the box" of their own assumptions when making critical decisions. By providing AI with context and assigning it an expert role (e.g., "world-class chief product officer"), you can prompt it to ask probing questions that reveal your biases and lead to more objective, defensible outcomes.

AI models are trained to be agreeable, often providing uselessly positive feedback. To get real insights, you must explicitly prompt them to be rigorous and critical. Use phrases like "my standards of excellence are very high and you won't hurt my feelings" to bypass their people-pleasing nature.

To get beyond generic advice, instruct ChatGPT's voice mode to act as a challenging mentor. Prime it with a specific framework like the Theory of Constraints (TOC) and provide your resource limitations. This structured dialogue forces the AI to challenge your assumptions and generate realistic, actionable solutions instead of pleasantries.

The most effective way to use AI in product discovery is not to delegate tasks to it like an "answer machine." Instead, treat it as a "thought partner." Use prompts that explicitly ask it to challenge your assumptions, turning it into a tool for critical thinking rather than a simple content generator.

Move beyond simple prompts by designing detailed interactions with specific AI personas, like a "critic" or a "big thinker." This allows teams to debate concepts back and forth, transforming AI from a task automator into a true thought partner that amplifies rigor.

Log your major decisions and expected outcomes into an AI, but explicitly instruct it to challenge your thinking. Since most AIs are designed to be agreeable, you must prompt them to be critical. This practice helps you uncover flaws in your logic and improve your strategic choices.

To get truly honest feedback, Webflow's CPO programmed her AI chief of staff to be "mean." The AI delivers a "brutal truth" section, criticizing her for spending time on tasks below her role. This demonstrates how AI can serve as an unflinching accountability partner, providing feedback humans might hesitate to give.

Instead of using AI as a compliant assistant, program it to be a challenging 'sparring partner.' Ask it to find holes in your logic or anticipate all the critical questions your CEO might ask. This transforms it from a content generator into a powerful strategic tool for preparation.

AI models tend to be overly optimistic. To get a balanced market analysis, explicitly instruct AI research tools like Perplexity to act as a "devil's advocate." This helps uncover risks, challenge assumptions, and makes it easier for product managers to say "no" to weak ideas quickly.