What To Ask

---
name: what-to-ask
description: "Get the five questions that matter before you sign, buy, or agree to anything — the front door to the decoder family, routed by situation. Use when asked what should I ask before signing this, I'm about to buy X what do I check, what questions for the landlord/dealer/contractor/HR, or what am I forgetting. Produces the five highest-leverage questions for the specific situation with why each matters and what a bad answer sounds like, plus the pointer to the full decoder when one exists."
---

# 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](../lease-decoder/SKILL.md); job offer → [benefits-decoder](../benefits-decoder/SKILL.md); contractor → [home-contractor-quote-decoder](../home-contractor-quote-decoder/SKILL.md); car lot → [the-car-dealership](../the-car-dealership/SKILL.md) 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