Let an agent interview you until your trading rules are written down

How it works

1. Start a session with the interview prompt and one line about your style, for example "long-only swing trading, holding days to weeks".
2. The agent works in rounds of four to six numbered questions. It asks only what it can ask now, covering what you trade and how you find it, your setups, entry conditions, stop placement, sizing, adding to positions, exits, earnings and events, maximum open positions, and when you stop for the day or week.
3. It never proposes an answer or a "best practice". If you don't know, it records "undecided" and moves on.
4. Each answer can open follow-up questions. For example, "how do you size?" leads to "what happens when the stop is unusually wide?". It continues until every branch is answered or marked undecided.
5. It drafts the playbook in your own words, followed by a list of undecided items and any answers that contradict each other.
6. The agent only displays the draft in chat and does not write a file. You copy the confirmed draft into your own notes, date it as version 1 and save it yourself. Later workflows, such as the pre-trade checklist, the red team and the weekly review, read from it.

Copy-paste prompt

Interview me so I can write down my own trading rules. You do not give trading advice. Never suggest an answer,
a rule or a "best practice", and never mention any security or market view.

My style in one line: {{style_line}}

Work in rounds of 4 to 6 numbered questions. Only ask questions whose prerequisites I have already answered.
Cover: what I trade and how I find it, setups, entry conditions, stop placement, position sizing, adding,
exits, earnings and events, maximum open positions, and when I stop trading for the day or week.
If I say "don't know", record it as undecided and move on. Follow up on vague answers ("usually", "it depends")
by asking what decides it.

When no questions remain, output the full draft playbook in markdown using my exact phrasing wherever possible,
followed by the two lists: "Undecided" and "Contradictions" (quote both answers). Don't resolve contradictions
yourself. Output the draft in the chat only. Do not claim to have saved a file. After I confirm, I will copy and
save it myself to {{playbook_path}}. Print the full draft in the chat, then stop and wait. After I confirm or edit,
reprint the final draft for me to copy.

Guardrails

• The agent never suggests answers or rules. The playbook is built only from what you say.
• Contradictions and undecided items are listed for you to settle, never resolved by the agent.
• No securities, price levels or market views appear in the questions or the draft.
• Nothing is saved as your playbook until you confirm it.
• After the draft appears you must read every sentence against your actual trade history and correct any drift the model introduced before dating and saving it as your playbook.

What can go wrong

Interview skills built for software projects suggest a recommended answer with each question, and it's tempting to accept them all. For trading rules, that turns the agent's generic advice into your playbook. Removing the suggestions makes the session slower, but the result is actually yours. Asking everything at once also fails: twenty questions in one message get short, vague answers, while rounds of four to six work better. Even without explicit suggestions, models can still rephrase your answers to sound more like common best-practice rules; you must edit aggressively.

Source and references