Critically Evaluate Your Plan with a 5-Step AI Prompt Sequence

What you’ll get

You will get a thoroughly evaluated plan, including a strong argument for its success, a detailed list of potential failures, and a “post-mortem” of what could go wrong. Finally, you’ll receive a revised plan and a clear recommendation to proceed or not. This approach works by forcing the AI to consider both the best and worst outcomes, giving you a more balanced perspective than a single prompt.

Tools you need

• ChatGPT (freemium): A popular AI chatbot for generating text and ideas.
• Claude (freemium): Another AI chatbot known for its conversational abilities and longer context windows.
• Gemini (freemium): Google’s AI chatbot, useful for a wide range of text generation tasks.

Steps

1. Make the strongest case for your plan: Open your chosen AI chat tool. Paste your plan into the chat, then use the following prompt. Replace [Your plan goes here] with your actual plan.

   Here is a plan I am considering: [Your plan goes here]. Before any criticism, make the strongest possible case for it. Assume I am right and explain why this is the correct move, including benefits I may not have noticed.

   You should receive a detailed argument supporting your plan, highlighting its potential benefits and why it’s a good idea.

2. Switch sides and list weaknesses: After the AI has made the case for your plan, send this next prompt in the same chat.

   Now switch sides completely. You are a skeptical expert who thinks this plan will fail. List every weakness, wrong assumption and risk, ranked by how likely each is to actually sink it. No softening.

   You will get a critical breakdown of your plan, listing potential flaws, risks, and incorrect assumptions, ordered by their severity.

3. Write a post-mortem of failure: Continue in the same chat. Imagine the plan has already failed and ask the AI to explain why.

   It is one year later and the plan failed. Write the honest post-mortem: what went wrong, in what order, and which early warning sign we ignored.

   The AI will provide a narrative of how the plan failed, detailing the sequence of events and overlooked warnings.

4. Rewrite the plan: Using all the information generated so far in the chat, ask the AI to revise your original plan.

   Using everything above, rewrite the plan. Keep what survived the criticism, fix what did not, and for each change say which weakness it addresses.

   You should receive a new, improved version of your plan, with explanations for each change and how it addresses previously identified weaknesses.

5. Write a decision memo: For the final step, ask the AI to summarize everything into a concise decision memo.

   Write a one page decision memo: the revised plan, the three biggest remaining risks, what would have to be true for it to work, and a clear recommendation, go or no go.

   You will get a summary document that includes the refined plan, key risks, conditions for success, and a final recommendation.

Original source

This structured prompt sequence was shared by Reddit user /u/Ok_Negotiation_2587 on the platform Reddit. The author designed it to overcome the common issue of single prompts only providing one perspective, by forcing the AI to argue both for and against a plan.

Notes & variations

• Common mistake: Do not try to combine these prompts into one long message. The power of this workflow comes from the AI processing each step sequentially, building on its previous responses within the same conversation. Wait for each answer before sending the next prompt.
• Tip for better results: Be as specific and detailed as possible when you first paste your plan in Step 1. The more context the AI has, the better and more relevant its analysis will be.
• Do you even need this?: For very simple, low-stakes decisions, a single prompt asking for pros and cons might be enough. This 5-step sequence is best for important plans or decisions where a thorough, multi-faceted evaluation is critical.