Pull up the last big decision you asked AI to help with: a pricing change, a hire, a new feature. Count how many times the model disagreed with itself in that thread. Zero, right? One prompt in, one confident answer out, no argument in the room.
Ok_Negotiation_2587 built a fix for this in r/PromptEngineering: a five step chain that forces the model to argue with itself before you commit to anything.
The core insight the Redditor makes: a single prompt can’t be for and against something at once. Ask for a critique, you get a critique. Ask for a plan, you get a confident plan. You never get the fight, because nothing forced the fight.
So instead of one prompt, run five messages in the same chat, one after another. Each message reacts to the answer before it.
Run The Five-Step Chain 📋
Paste your plan into the first message and swap in your own details for [plan].
Step 1, make the strongest case first:
Here is a plan I am considering: [plan]. 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.
Step 2, flip completely to the skeptic:
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.
Step 3, jump a year ahead and assume it already failed:
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.
Step 4, rebuild with everything on the table:
Using everything above, rewrite the plan. Keep what survived the criticism, fix what did not, and for each change say which weakness it addresses.
Step 5, force a real verdict:
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.
The order matters more than the individual prompts. Step 1 stops the model from anchoring on criticism it hasn’t earned yet, so the case for the plan gets a fair hearing. Step 3 is the one people skip. It’s also the one that actually finds the real problem, because “it already failed” pulls a different answer than “what could go wrong” does.
What Your Results Mean 🧭
If step 2 and step 3 land on the same weak point twice, that’s not a coincidence you can shrug off. That’s the model converging on your plan’s actual failure point from two different angles.
If step 1 comes back thin, short on real benefits, no strong case, that’s a signal too. A plan that can’t get a good defense from a model that’s trying its hardest to defend it probably isn’t ready.
By step 5, the memo is built out of an argument the model already had with itself. That’s the whole point of running five separate messages instead of one prompt asking for “pros and cons.”
Extra Tips 💡
Tell the model upfront what it must not invent. One commenter on the thread flagged why this matters. The critique stage is exactly where a model starts adding plausible sounding risks and numbers that were never in your plan. A quick line at the top of step 2 keeps it honest: “don’t invent facts not in the plan.”
Run this before anything that’s actually hard to reverse. The original poster runs it before pricing changes, hires, and any feature that takes more than a week. It’s already talked them out of two of those calls.
Keep the five messages in one chat, in order, waiting for each answer before sending the next. Running them out of order, or all at once, defeats the purpose. The model needs to see its own step 1 answer before it can argue against it in step 2.
Another commenter pointed out the real unlock isn’t the wording of any single prompt. It’s forcing the switch across separate messages. Asking for pros and cons in one shot just produces a politely balanced answer, not a real fight.
Try It On Your Next Big Call 🚀
Next time you’re staring at a plan you’re not sure about, don’t ask one prompt for a verdict. Run the five steps, let the model fight itself for a few minutes, and see what survives! Drop your own version of the “skeptic” step in the comments. Everyone phrases that one a little differently.
Frequently Asked Questions
Q: How do I prepare my plan before starting this sequence?
Start with whatever you’ve written down, it doesn’t need to be polished. The more specific you are about timeline, budget, and key assumptions, the better the AI can actually critique it. Vague ideas don’t give the model enough concrete ground to work with.
Q: How do I prevent the AI from inventing false risks or numbers?
Call it out when it happens, and tell the model to stick to analyzing what’s actually in your plan, mark unknowns explicitly instead of filling gaps with plausible-sounding details. This matters most in the critique step, where the model tends to add authoritative-sounding risks that might not apply to your situation.
Q: Why are separate messages so important? Can’t I just ask for pros and cons in one prompt?
One prompt usually produces a balanced answer where the model hedges everything. Separate messages force the model to fully commit to each position, especially making the strongest case *before* switching to skepticism, which gives you real disagreement instead of diplomatic hedging.
Q: Do I need to fact-check every risk the AI lists?
Not every one, but verify the ones that feel most likely in your specific situation. Use the AI’s risks as a starting point to find blind spots you might have missed, then apply your own judgment about what actually matters in your context.
Q: Can I shorten this to save time?
You can run fewer steps, but don’t skip step 3 (the post-mortem). That’s where the model finds real failure modes instead of generic risks. The separate-message structure is also critical, that’s what prevents hedging.
The 5 prompt sequence I run before committing to any plan, because one prompt never argues with itself
by u/Ok_Negotiation_2587 in PromptEngineering