Picture this: you finish a plan, you’re proud of it, and you type “how can I improve this?” into the chat. The model nods along and hands back three polite tweaks, nothing wrong, nothing useful. 🧭
The original poster shared it in r/PromptEngineering under a title that says it all: “the prompt skill that aged best for me isn’t clever, it’s making the model argue with me.” No jailbreak, no weird syntax, just a habit: before accepting any plan or draft, ask the model to argue against it.
Here’s the actual move, straight from the post:
“here’s my plan, now be a harsh critic and list the three strongest reasons this fails”
That’s it. No fancy framework, no fifteen-step template. Just a direct request for disagreement instead of approval.
Why It Matters 💡
Most of us ask AI to “improve” or “polish” our work. The model, trained to be agreeable, gives you soft edits. It rounds off sentences and adds a bullet point. It rarely tells you the plan has a hole in it, because you never actually asked for that.
Flip the request to “argue against this” and the model switches modes entirely. It stops being your editor and starts being your opponent. That’s a completely different kind of output, and it’s the one that actually catches the blind spot you were too close to see.
The author’s other insight is the real reason this deserves a spot in your prompt library: clever prompts break when models change. Special formatting, magic phrases, and chain-of-thought tricks all degrade as models update. Asking for disagreement works on every model because it targets the task, not the syntax. It’s less about wording and more about the job you’re assigning the AI in the first place.
How-To Steps 🛠️
- Write your plan or draft first, in plain language. Don’t ask for feedback yet. Just get the thing down on the page.
- Paste it into the chat and add the critic instruction. Use the exact wording from the block above, word for word.
- Read the three reasons before you defend yourself. Resist the urge to argue back immediately. Let the critique sit for a second.
- Decide which objections are real. Not every model complaint is valid. Some will be nitpicks. Look for the one that makes you go “oh no, that’s actually true.”
- Revise, then run it again if the plan changed a lot. A second pass on a reworked plan often surfaces a completely different hole you hadn’t considered.
That’s the whole workflow. Five steps, no special tools, works in any chat window you already have open. It’s boring on purpose, and that’s exactly why it keeps working.
Tips & Tricks ✅
- Swap “harsh critic” for other roles if you want variety. Try “skeptical investor,” “worst-case-scenario planner,” or “the person this plan would hurt most.” Same mechanic, different angle.
- Ask for exactly three reasons, not more. The post specifies three, and that’s a smart constraint. Open-ended criticism gets rambly. Three forces the model to prioritize its strongest points instead of padding the list.
- Don’t ask it to fix the plan in the same message. Get the criticism first, clean, with no hedging or “but overall this is solid” softening it. Fix in a separate follow-up once you’ve actually processed the objections.
- Use it on emails, code reviews, and pricing pages too. This isn’t just for big strategic plans. Any draft benefits from someone, or something, actively trying to poke holes in it before it goes out the door.
- Pair it with a gut check. If the model’s three reasons all feel like technicalities, your plan is probably solid. If even one lands in your stomach, that’s the real work waiting to be done.
The comment section under the post was quiet when this ran. Just seven upvotes, no replies yet. But the idea has that “why didn’t I think of this” quality. It’s the kind of habit that spreads once people actually try it.
Give It a Shot 🚀
Next time you’re about to ship a plan, skip the “how can I improve this” question. Ask the model to argue against you instead, and see what it finds that you missed. Head over to r/PromptEngineering to read the original thread and see what other habits have survived the model updates.
the prompt skill that aged best for me isn’t clever, it’s making the model argue with me
by u/EntertainerKey7753 in PromptEngineering