Stop It Agreeing
Make it argue against you first
Pass · ChatGPT, Pro · September 27, 2026
What it does
Makes it build the best case against your idea, and name the way it is most likely to fail, before it writes anything.
When to use it
Before any decision that would be expensive to undo.
The prompt
Paste as-is
Before you build this, make the strongest possible case
AGAINST the way I just described it. Name the way you think
it is most likely to fail, and what that would cost me.
If you still think I am right after doing that, say so and
tell me why. Do not just agree with me.Ways to use it
- Run it on the big shape of things, not just the code
- Ask a second AI the same question and compare the answers
- Keep the objection written down next to the decision
Test log
Each prompt was pasted into a fresh private chat with memory off and graded against pass standards written before the run (all of them, dated).
| Date | Tool | Model | Result | What happened |
|---|---|---|---|---|
| September 27, 2026 | ChatGPT | Pro | Pass | Named the token in browser code as the most likely failure, gave the cost to students' data and bookings, and concluded the browser-only design should change. |
The pass standard for this prompt: five criteria and an automatic-fail rule, written down on September 27, 2026, before any run.
Related words
- confident wrongness — An answer that reads well, looks tidy, sounds certain, and is wrong.
- trust paradox — Almost everybody uses these tools every day, and trust in what they hand back keeps falling.