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.

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.

Don't let performance reviews sit in a folder. Upload your official review and peer feedback into a custom GPT to create a personal improvement coach. You can then reference it when working on new projects, asking it to check for your known blind spots and ensure you're actively addressing the feedback.

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.

By creating a private GPT and uploading all relevant business information, you can build an AI consultant that understands your specific context. This helps clarify priorities, vet new strategies, and maintain focus.

Generative AI models often have a built-in tendency to be overly complimentary and positive. Be aware of this bias when seeking feedback on ideas. Explicitly instruct the AI to be more critical, objective, or even brutal in its analysis to avoid being misled by unearned praise and get more valuable insights.