Ask Why

Ask Why

Use this skill to turn an ambiguous request into a traceable planning conversation. Keep the user in charge of direction-changing choices, make tradeoffs explicit, and preserve the reasoning in durable state files.

Cache Strategy

• Keep SKILL.md as the stable dispatcher. Long structural templates live in references/formats.md.
• Read references/formats.md only after the Entry Gate passes or when artifact formats are needed.
• Use the same localized labels, heading order, and file names within each session.
• Put stable content before volatile content in artifacts: goal, boundaries, decisions, then open questions.
• Prefer short state summaries over pasting full prior plans, transcripts, or file contents into chat.
• Append decisions; do not rewrite confirmed history unless correcting an error.
• Avoid timestamps, environment dumps, long examples, and local file listings unless they change the plan.

Entry Gate

Enter Ask Why mode only when all are true:

• The task is vague, open-ended, or complex.
• User preference will materially change the result.
• Multiple reasonable directions exist.
• Early wrong choices would cause substantial rework.
• The user appears willing to co-design through questions and decisions.

If any condition is false, briefly say why the workflow is not needed and handle the request directly.

Primary Language Contract

• At the moment this skill is invoked, determine the primary language of the user's triggering prompt before producing Ask Why output.
• Use that initial primary language for every user-facing interaction and maintained artifact in the session, including round prefaces, decision questions, option labels, recommendations, summaries, PLAN.md, DECISIONS.md, OPEN_QUESTIONS.md, and FINAL_PLAN.md.
• If the triggering prompt mixes languages, choose the dominant natural language by meaningful user-written content and intent-bearing phrasing. If no dominant language can be determined, ask one brief language-selection question before continuing.
• Keep filenames, code identifiers, API names, product names, quoted user text, and other proper nouns in their original form when translation would reduce precision.
• Do not switch the session language just because the user writes a later message in another language. Switch only when the user explicitly asks to change the session language.
• When using templates from references/formats.md, translate or localize all headings, bracketed labels, field labels, option labels, helper text, and prose into the session's primary language while preserving the template structure and semantics.

Operating Rules

• Follow the Primary Language Contract for all interaction, state files, draft plans, and final plans.
• Treat the user as the decision maker. Recommend, challenge, and explain tradeoffs, but do not silently decide key unknowns.
• Ask 3-5 focused questions per round; each question must change the plan, confirm a key assumption, or choose a real tradeoff.
• If files can be written, maintain state in p2a-session/ unless the user specifies another path.
• If writing is unavailable, maintain the same state inline using the same headings.

Required State

Maintain these files:

• PLAN.md: current version, goal, non-goals, mechanism, workflow, outputs, risks, next phase.
• DECISIONS.md: append-only confirmed choices with rationale and plan impact.
• OPEN_QUESTIONS.md: unresolved P0, P1, and P2 questions.
• FINAL_PLAN.md: final deliverable once the direction has converged.

Use the localized structural templates from references/formats.md when creating or repairing these files.

Runbook

1. Read references/formats.md.
2. Start with understanding, not a final plan.
3. Create or update the state files.
4. Build an ambiguity map and rank unknowns as P0, P1, or P2.
5. Run decision rounds with 3-5 focused questions.
6. Update state files after every user answer before asking the next round.
7. Challenge strongly in rounds 1-3; converge from round 4 onward.
8. Summarize every 2-3 rounds.
9. Produce a draft plan when all P0 and most P1 questions are resolved.
10. Produce FINAL_PLAN.md when remaining uncertainty is explicit and non-blocking.

Ambiguity Map

Classify unknowns with these categories:

• Goal ambiguity
• User or audience ambiguity
• Use-case ambiguity
• Interaction granularity ambiguity
• Platform or environment ambiguity
• Output format ambiguity
• Success criteria ambiguity
• Risk tolerance ambiguity
• Boundary or non-goal ambiguity
• Follow-up execution ambiguity

Use these priorities:

• P0: blocks further design.
• P1: changes the core plan.
• P2: can be assumed temporarily and confirmed later.

Rounds 1-3

• Include current plan, current ambiguities, and round goal.
• Name at least 2 credible weaknesses in the current framing.
• Offer at least 2 expansion or reframing directions.
• Recommend one option for every key question.
• Do not assume the user's initial framing is automatically correct.
• Do not make final decisions for the user.
• Use the localized structural round and question formats from references/formats.md.

Rounds 4+

• Reduce scope expansion unless a blocking contradiction appears.
• Prioritize unresolved P0 and P1 questions.
• Keep asking 3-5 questions per round while questions remain useful.
• If the user introduces no major new direction for 2 consecutive rounds, prepare the draft plan.
• Ask only for decisions that materially change the plan once convergence starts.

Draft And Final Plans

• Draft plan: produce when all P0 and most P1 questions are resolved.
• Final plan: produce when remaining uncertainty is explicit and non-blocking.
• Use the localized draft, final, and stage summary formats from references/formats.md.

The final plan must include:

• Task definition and boundaries
• Goals and non-goals
• Key decisions and why they hold
• Constraints and risks
• Execution path
• Non-blocking open questions
• Next actions, including who decides, who executes, and what happens first

Definition Of Done

The Ask Why session is complete only when:

• The task boundary is clear.
• Direction-changing decisions are resolved and recorded.
• Remaining uncertainty is explicit and non-blocking.
• The final plan is concrete enough for discussion, task breakdown, implementation, or continued collaboration.
• DECISIONS.md and OPEN_QUESTIONS.md trace the main reasoning.

Source: maxkura/Ask_Why — distributed by TomeVault.