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Red-team my trade thesis (pre-mortem + risk map)

Before you put on or upsize a position — or send desk color to a client — force a structured pre-mortem so you are not just reading your own book back to yourself.

The prompt — copy and run it

Act as the sharpest bear on the other side of my trade. I will give you the thesis, the instrument, the entry, the sizing, and my time horizon. Do this:

1) Restate my thesis in one sentence and name the 3 assumptions it silently depends on.
2) Pre-mortem: it is my horizon-end and the trade lost money. Give the 5 most likely reasons, ranked, and the earliest observable signal that each is starting to happen.
3) Map the risks: what's idiosyncratic vs factor/macro, what's crowded, what's the liquidity/gap risk, and what event dates fall inside my horizon.
4) Tell me what price/data would FALSIFY the thesis (my exit), and what would make me want to add.
5) Give a one-line 'the market is offering me this trade because ___' — i.e. what edge or risk premium am I actually being paid for.

Be concrete, no hedging language. Do NOT tell me to buy or sell — pressure-test only. Here is the setup:
[THESIS, INSTRUMENT, ENTRY, SIZE, HORIZON]

Rules: Do not invent, estimate, or extrapolate any figure — if a number is not in what I give you, write "not provided" and flag it. Mark every claim I should verify externally before relying on it. Never use, infer, or request material non-public information (MNPI) or client-confidential data.

How to use this prompt

  1. Copy the full prompt above with the Copy button.
  2. Fill in your inputs. Replace each bracketed placeholder with your specifics: [THESIS, INSTRUMENT, ENTRY, SIZE, HORIZON]
  3. Paste into ChatGPT, Claude, or Gemini and run. Read the reality guardrail below before you act on the output.

Why this prompt works

A structured pre-mortem + falsification level is how disciplined desks avoid marrying a position. The 'why is the market offering me this' line surfaces whether you're paid for edge or just taking hidden risk. It explicitly refuses to give directional advice.

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Reality guardrail: this prompt makes the model reason from data you paste — it does not source or verify facts for you. Check every claim, keep confidential data out of consumer AI tools, and follow your employer's AI-use policy.

Frequently asked

When should I use this prompt?

Before you put on or upsize a position — or send desk color to a client — force a structured pre-mortem so you are not just reading your own book back to yourself.

Why does this prompt work?

A structured pre-mortem + falsification level is how disciplined desks avoid marrying a position. The 'why is the market offering me this' line surfaces whether you're paid for edge or just taking hidden risk. It explicitly refuses to give directional advice.

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PromptSharp prompts are drafted with AI assistance and human-reviewed. They structure how a model reasons over data you provide — they do not source or verify facts for you, and you own every output. Nothing here is financial, legal, tax, or investment advice. Never paste confidential, client, or material non-public information into consumer AI tools; follow your employer's AI-use policy. © 2026 PromptSharp.