Get a Skeptical AI Perspective on Big Decisions with ChatGPT

What you’ll get

You will receive a detailed, skeptical analysis of a big decision you are considering, highlighting potential risks, fragile assumptions, and blind spots you might have. This approach works by forcing the AI to argue against your decision first, which helps you uncover weaknesses and make a more informed choice.

Tools you need

• ChatGPT (freemium): An AI chatbot that can generate human-like text and analyze information.

Steps

1. Open ChatGPT: Go to chatgpt.com using your web browser on your phone or computer. Log in or sign up if you haven’t already. You should see the chat interface ready for your input.

2. Prepare your decision details: Before you paste the prompt, gather the specific information about your decision. You will need to clearly state:

   • [what I'm planning to do]: The exact decision you are considering.
   • [my reasoning]: Your main reasons for thinking this decision is a good idea.
   • [time, money, reputation, whatever]: What important things are at risk if the decision goes wrong.

3. Paste the skeptical advisor prompt: Copy the entire prompt below and paste it into the message box in ChatGPT. Carefully replace each bracketed section (like [what I'm planning to do]) with your specific details from the previous step.

   You are my most skeptical advisor. I'm about to make a decision and I need you to try to talk me out of it before I commit.
   
   THE DECISION: [what I'm planning to do]
   WHY I THINK IT'S RIGHT: [my reasoning]
   WHAT'S AT STAKE: [time, money, reputation, whatever]
   
   Do this, in order:
   Steelman the OPPOSITE choice - make the strongest case for not doing this, better than I could.
   Name the 3 assumptions I'm relying on that, if wrong, would break the whole plan. Which is the most fragile?
   Tell me what I'm probably not seeing because I already want this to be true (my blind spots here).
   If I do it anyway, what's the single biggest risk, and how would I cut it in half?
   Then - and only then - give me your honest verdict: proceed, adjust, or drop it. Commit to one. Don't be balanced for the sake of it. Push.

   You should see ChatGPT begin to generate a detailed response, following each instruction in the prompt step-by-step, providing a critical analysis of your decision.

Original source

This workflow was shared by Reddit user /u/Ok_Negotiation_2587 on the platform Reddit. They developed this specific prompt to get an unbiased, critical perspective from AI before making important decisions.

Notes & variations

• Free-tier alternatives: You can also use other freemium AI chatbots like Gemini (gemini.google.com) or Claude (claude.ai) for this workflow. The prompt should work similarly across these platforms.
• Common mistake: Not providing enough specific detail in the bracketed sections. The AI’s analysis will only be as good as the information you give it. Be as clear and thorough as possible.
• Tip for better results: Take your time to clearly articulate your decision, your reasoning, and what’s at stake. The more context you provide, the more insightful and helpful the AI’s skeptical feedback will be.