What To Ask

What To Ask Skill

Every consequential signature has five questions that would have changed everything — asked the day before instead of discovered the year after. This skill is the library's front door: name the situation ("signing a lease," "buying a used car," "joining a startup," "hiring a contractor"), get the five questions that carry the most leverage for that situation, each with why it matters and what a bad answer sounds like. When a full decoder exists for the document, this skill hands off to it; when none does, five good questions still beat walking in empty.

What This Skill Produces

• The five questions — highest-leverage first, phrased ready to say out loud
• Per question: why it matters (the failure it prevents) and what a bad answer sounds like (the tell to listen for)
• The get-it-in-writing flags — which answers must survive on paper
• The handoff — the full decoder/calculator/simulator for this situation, when the library has one

Required Inputs

Ask for these if not provided:

• The situation — what's being signed/bought/agreed, with whom, and when (tomorrow changes the advice from "research" to "triage")
• The stakes and the worry — money involved, and the thing they're privately nervous about (the fifth question is usually theirs)
• What's already known — documents in hand get routed to their decoder; verbal-only situations get the questions that force things onto paper

Framework: The Question-Selection Rules

1. Leverage order, not checklist order: the five are chosen by expected-cost-prevented, not thoroughness — the question that voids the deal outranks ten that adjust it. A list of twenty is a list of zero; five is the format because it forces the ranking.
2. Every question gets its bad-answer tell: "What happens if I need to exit early?" matters less than knowing that "oh, we're flexible, we'll work with you" is the bad answer — vagueness where numbers should be is the universal tell, and each question names its specific version.
3. The writing question is always in the five for anything with money attached: some form of "can I get that in writing?" — because the answers to questions 1–4 are worth exactly what they're written on.
4. Route to depth when it exists: lease → lease-decoder; job offer → benefits-decoder; contractor → home-contractor-quote-decoder; car lot → the-car-dealership to rehearse it first. The five questions are the door; the decoder is the room.
5. Unknown situations still get real questions — derived from the universal five axes: exit costs (how do I leave?), change costs (what can they change on me?), the money's full shape (what's the all-in number?), failure modes (what happens when something goes wrong?), and verification (how do I check what you just told me?). Any situation on earth maps onto those.

Output Format

Before you [sign/buy/agree]: [situation]

The Five

1. "[The question, verbatim]" Why: [the failure it prevents] · Bad answer sounds like: "[the tell]" · [📝 get in writing]

[…2–5, same shape…]

If You Only Ask One

[Which, and why it carries the most weight here]

Go Deeper

[The library's full treatment for this situation, linked — or "no decoder yet; the five axes above are the map"]

Quality Checks

• Exactly five questions, leverage-ranked — not a padded checklist
• Every question has a bad-answer tell, specific to it
• The in-writing flag appears wherever money does
• The user's stated private worry became one of the five
• The handoff link appears when the library covers the situation

Anti-Patterns

• Do not exceed five — the ranking discipline is the product; a sixth question weakens the first
• Do not ask questions the user can't act on — every answer must change something
• Do not phrase questions adversarially — the counterpart is a person; the tells do the detecting
• Do not skip the handoff to save face — five questions are the trailer, not the movie
• Do not generate generic questions for a specific situation — "what are the terms?" is what this skill exists to replace