The Sceptic’s Question · 1 of 5
Make AI argue the other side of your trade.
In the first brief we set out five questions to ask AI before any trade. This week, the first one:
What is the strongest argument against this trade?
It sounds like a small change from the question most traders already ask. It isn't.
"What are the risks of this trade?"
Ask that and you'll get a tidy list. Volatility. News risk. The trend could reverse. Slippage. Every item is true, none of them is specific to your trade, and none of them asks anything of you. You read the list, you agree with it, and you place the trade anyway.
A list is easy to dismiss. An opponent isn't.
The word that matters is strongest. It forces the AI to pick one argument, commit to it, and build it properly, the way the trader on the other side of your position would.
Because there is a trader on the other side. Every time you buy, someone is selling to you, and they have reasons. You don't have to agree with them. You do need to know what they are.
A prompt that does the job
"Here is my trade idea: [instrument, direction, entry, stop, and the reason in two or three sentences]. Act as an experienced trader who is taking the opposite position. Give me the single strongest argument for your side. Make it specific to this setup, not generic market risk. Then tell me what evidence would prove you right."
Three things make it work:
- It gives the AI your actual reasoning, so it has something real to push against.
- It assigns a side. AI coaches lean towards agreeing with you unless you tell them not to.
- It asks what would prove the other side right, which turns an argument into something you can watch for.
What to do with the answer
Read it as if it came from someone you respect. Then sort it into one of three piles:
- You can answer it with evidence. Good. Write the answer down. You've just made your thesis stronger.
- You can't answer it, but it's unlikely. Fine, but now it belongs in your plan. Where does your stop sit if this argument turns out to be right?
- You can't answer it, and it's plausible. That's the trade telling you something. Reduce size, wait, or pass.
The point isn't to talk yourself out of every trade. Most of the time you'll still take it.
But you'll take it knowing exactly what you're betting against, and that's a very different position from hoping nothing goes wrong.
Next week: what assumptions am I making?