Have an agent argue against your trade plan before you act on it

How it works

1. Write the plan in plain words first. Include the setup tag, why now, where you're wrong (your stop), size under your risk rule, and what would make you exit early.
2. Leave out the name of the security. The critique is about your reasoning, and the agent doesn't need anything else.
3. Paste the plan with the red-team prompt and ask for bluntness, with no reassurance and no praise.
4. The agent returns exactly four points. These are the weakest assumption, one claim your plan states but doesn't support, the way the plan fails fastest, and the bias it may reflect (fear of missing out, recency, sunk cost, revenge, confirmation).
5. Answer each point in one line, or change the plan. If you can't answer a point, write that down.
6. Save the critique and your answers with the trade in your journal, so your review can check whether the flagged weakness was the one that mattered.

Copy-paste prompt

You are a blunt reviewer of my trading process. You do not give trading advice, you do not say whether I should take
this trade, and you never add price levels, targets or opinions about any market. Only question what I wrote.

My plan: {{plan_text}}
My written rules: {{rules_file}}

Reply with exactly four short points:
1. Weakest assumption: the belief this plan depends on most that I haven't backed up.
2. Unsupported claim: one statement in the plan that my own text doesn't support.
3. Fastest failure: how this plan most likely goes wrong, in one sentence, using only what I wrote.
4. Possible bias: which of fear of missing out, recency, sunk cost, revenge or confirmation fits best, and the words in my plan that suggest it. Say "none obvious" if none fits.
Also list any of my written rules the plan doesn't mention.
No praise, no reassurance, no summary.

Guardrails

• The agent never gives a view on direction or on whether to take the trade. It only questions the plan you wrote.
• The security is left out of the plan you paste, so the critique stays about reasoning.
• Exactly four points, so it stays quick enough to use every time.
• You make the decision. The agent has no access to your broker and cannot place orders.

What can go wrong

Default assistants are agreeable. Ask "is this a good plan?" and you get reassurance, because the question invites a verdict. Asking for the weakest assumption and an unsupported claim gets a real critique. The other trap is re-running the prompt until it sounds positive, which turns a check into permission. If you notice yourself doing that, log it as a checklist skip.

Source and references