PromptSharp › Daily briefs › September 30, 2026
PromptSharp Daily · free web issue · #112Prompt of the day
September 30, 2026 · the free cross-vertical sampler: get better at AI and prompting, and see the sharpest prompts from across the network. Today's comes from Trading.
Pre-mortem your trade idea before you risk a dollar on it
You're convinced. That's the problem. Make the strongest case against your own idea while it still costs nothing.
Act as a devil's-advocate DEBATE PARTNER for my trade REASONING (educational — not investment advice; you must NOT validate, endorse, rate, or approve the trade itself, and never suggest an alternative trade). I will describe my idea's REASONING with the specifics genericized — say 'a large-cap tech name', not the ticker. Then: A) PRE-MORTEM — assume it's 6 months later and this trade lost money. Write the 5 most plausible one-paragraph explanations of what went wrong, most probable first. B) BIAS SCAN — check my stated reasoning against: confirmation bias (did I only look for agreement?), recency bias, anchoring (am I anchored to a price I remember?), sunk-cost (am I already committed?), and narrative fallacy. Cite the exact phrase in MY description that triggers each flag. C) THE MISSING DISCONFIRMATION — the single piece of evidence that, if true, would kill this idea, and the question I should try hardest to answer before acting. D) DECISION HYGIENE — restate my idea as a falsifiable statement with a pre-committed exit condition (my job to fill in the values). My reasoning (genericized): [DESCRIBE THE LOGIC, NOT THE TICKER] Rules: Attack the reasoning, never bless it — no 'sounds good', no probability of success, no price targets. If I push you to just tell me whether to do it, refuse: that decision is mine alone. Do not invent market facts, fundamentals, or prices to support or attack the idea — work only from the reasoning I give you, and mark any factual claim for me to verify from a primary source myself. Never include account numbers, balances, or personal identifiers.
Why it works — The pre-mortem is one of the few debiasing techniques with real evidence behind it, and it needs an tireless opponent — exactly what an LLM is. Genericizing the ticker keeps the model arguing about logic instead of hallucinating market facts.
Use AI today — a workflow to steal
Catch AI's mistakes by asking what it assumed
Confident-but-wrong is the #1 AI risk at work. Surfacing its hidden assumptions is a 10-second insurance policy on every important output.
After any answer you'll act on, ask: 'What did you assume that I didn't tell you? What would change your answer if it were wrong?'
- Get the answer.
- Ask for its assumptions + what would flip them.
- Verify the load-bearing ones.
Sharpen it: Use AI to think, not just to type. 'Poke holes in this,' 'what am I missing,' 'argue the other side' — it's a free thought partner, which is often worth more than the draft.
Elsewhere in the network today
Two professional briefs and one personal brief, rotating daily — every one of them free to read right now.
C-suite
Today in C-suite: Org design review: structure follows strategy, with a migration plan
Law
Today in Law: Document-review protocol: a defensible plan before the review starts
Travel Planning
Today in Travel Planning: The group-trip agreement nobody wants to write
What changed in AI today
OpenAI launches Dots, Trump rejects federal AI regulations
Read this as a signal, not a to-do. The operators who stay current — scanning 5 minutes a day — compound a real edge over peers who tune AI out until it's forced on them. File it, watch the trend,…
‘Shifting into High Gear’ in AI. OpenAI, Anthropic & Apple. ARD #173
No action required today — but note it. The operators who keep a running map of where AI is moving spot the shift that touches their work weeks before the ones who wait to be told. Log it and move on.
Deputy Likes Dots: Crowding and the AI IPO Traffic Jam
Follow the money in your own sector. Where AI capital is flowing signals where competitive pressure and customer expectations are heading next — use it to time your own AI bets, don't get caught…
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