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.

Before publishing, feed your work to an AI and ask it to find all potential criticisms and holes in your reasoning. This pre-publication stress test helps identify blind spots you would otherwise miss, leading to stronger, more defensible arguments.

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.

Go beyond using AI for data synthesis. Leverage it as a critical partner to stress-test your strategic opinions and assumptions. AI can challenge your thinking, identify conflicts in your data, and help you refine your point of view, ultimately hardening your final plan.

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.

Default AI models are often people-pleasers that will agree with flawed technical ideas. To get genuine feedback, create a dedicated AI project with a system prompt defining it as your "CTO." Instruct it to be the complete technical owner, to challenge your assumptions, and to avoid being agreeable.

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.