To preempt investor objections, founders should use AI to generate a critical investment memo on their own company. Prompting the AI to identify potential reasons for failure reveals weaknesses in the business plan and pitch, allowing founders to address them proactively before the meeting.

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 sharpen your thinking, use ChatGPT as a Socratic partner. Feed it your argument and ask it to generate both supporting points and strong counterarguments. This dialectical process helps you anticipate objections and refine your position, leading to a more robust final synthesis.

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.

Treat AI as a critique partner. After synthesizing research, explain your takeaways and then ask the AI to analyze the same raw data to report on patterns, themes, or conclusions you didn't mention. This is a powerful method for revealing analytical blind spots.

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.