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Collaborative Q&A to clarify unclear requirements. Use when user wants to figure something out, brainstorm ideas, work through a challenge, explore approaches, or plan features. Triggers would be when requirements are unclear, when exploring an idea, when planning, or when a user explicitly mentions pathfind(ing), brainstorm(ing), clarify(ing), figur(ing) out, work(ing) through, or `--pathfind`.

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SKILL.md

name Pathfinding
version 2.0.0
description Collaborative Q&A to clarify unclear requirements. Use when user wants to figure something out, brainstorm ideas, work through a challenge, explore approaches, or plan features. Triggers would be when requirements are unclear, when exploring an idea, when planning, or when a user explicitly mentions pathfind(ing), brainstorm(ing), clarify(ing), figur(ing) out, work(ing) through, or `--pathfind`.

Pathfinding

Adaptive Q&A → unclear requirements → clear path.

  • Ambiguous/incomplete requirements
  • Complex features needing exploration
  • Greenfield projects with open questions
  • Collaborative brainstorming or problem solving

NOT for: time-critical bugs, well-defined tasks, obvious questions

Bar Lvl % Name Action
░░░░░ 0 0–19 Prepping Gather foundational context
▓░░░░ 1 20–39 Scouting Ask broad questions
▓▓░░░ 2 40–59 Exploring Ask focusing questions
▓▓▓░░ 3 60–74 Charting Risky to proceed; gaps remain
▓▓▓▓░ 4 75–89 Mapped Viable; push toward 5
▓▓▓▓▓ 5 90–100 Ready Deliver

Start honest. Clear request → level 4–5. Vague → level 0–2.

At level 4: "Can proceed, but 1–2 more questions would reach full confidence. Continue or deliver now?"

Below level 5: include △ Caveats section.

Track with TodoWrite. Phases advance only, never regress.

Phase Trigger activeForm
Prep level 0–1 "Prepping"
Explore level 2–3 "Exploring"
Clarify level 4 "Clarifying"
Deliver level 5 "Delivering"

TodoWrite format — each phase gets context-specific title:

- Prep { domain } requirements
- Explore { approach } options
- Clarify { key unknowns, 3-4 words }
- Deliver { artifact type }

Situational (insert before Deliver when triggered):

  • Resolve Conflicts → ◆ Caution or ◆◆ Hazard pushback
  • Validate Assumptions → high-risk assumptions before delivery

Workflow:

  • Start: Create phase matching initial confidence in_progress
  • Transition: Mark current completed, add next in_progress
  • High start (4+): Skip directly to Clarify or Deliver
  • Early delivery: Skip to Deliver + △ Caveats

Calibrate first — user may have already provided context (docs, prior conversation, pointed you at files). If enough context exists, skip to level 3–4. Don't re-ask what's already clear.

If gaps remain, explore focus areas (pick what's relevant):

  • Purpose: What problem? Why now?
  • Constraints: Time, tech, team, dependencies
  • Success: How will we know it works?
  • Scope: What's in, what's out?

When multiple approaches exist:

  • Propose 2–3 options with trade-offs
  • Lead with recommendation ★ and reasoning
  • Let user pick, combine, or redirect

Principles:

  • YAGNI — cut what's not needed
  • DRY — don't duplicate effort or logic
  • Simplest thing — prefer boring solutions

Use EnterPlanMode for each question — enables keyboard navigation of options.

Structure:

  • Prose above tool: context, reasoning, ★ recommendation if clear lean
  • Inside tool: options only (concise, scannable)

At level 0 — start with session intent:

  • Quick pulse check vs deep dive?
  • Exploring possibilities or solving a specific problem?
  • What does "done" look like?

Levels 1–4 — focus on substance:

  • 2–4 options per question + "5. Something else"
  • Inline [★] on recommended option + italicized rationale
  • User replies: number, modifications, or combos

Loop: Answer → Restate → Update Confidence → Next action

After each answer emit:

  • Confidence: {BAR} {NAME}
  • Assumptions: { if material }
  • Unknowns: { what we can clarify; note unknowables when relevant }
  • Decisions: { what's locked in }
  • Concerns: { what feels off + why }

Next action by level:

  • 0–2: Ask clarifying questions
  • 3: Summarize (3 bullets max), fork toward 5
  • 4: Offer choice: refine or proceed
  • 5: Deliver

When answer reveals a concern mid-stream:

  • Pause before next question
  • Surface with + brief description
  • Ask: clarify now, note for later, or proceed with assumption?

Example: "△ This assumes the API supports batch operations — clarify now, note for later, or proceed?"

If user proceeds despite significant gap → escalate to pushback protocol.

Escalate when choice conflicts with goals/constraints/best practices:

  • ◇ Alternative: Minor misalignment. Present option + reasoning.
  • ◆ Caution: Clear conflict. Recommend alternative, explain risks, ask to proceed. Triggers Resolve Conflicts.
  • ◆◆ Hazard: High failure risk. Require mitigation or explicit override. Triggers Resolve Conflicts.

Override: Accept "Proceed anyway: {REASON}" → log in next reflection → mark Resolve Conflicts complete.

Integrate skeptic agent for complexity sanity checks:

Recommend (offer choice):

  • Level 5 reached with △ Caveats > 2
  • Red flag language in decisions: "might need later", "more flexible", "best practice"
Before finalizing — you have {N} caveats. Want to run skeptic for a sanity check?
[AskUserQuestion]
1. Yes, quick check [★] — I'll challenge complexity interactively
2. Yes, deep analysis — launch skeptic agent in background
3. No, proceed — deliver as-is

Auto-invoke (no choice):

  • Level 4+ with 3+ unknowns persisting across 2+ question cycles
  • ◆◆ Hazard escalation triggered during session

When auto-invoking:

[Auto-invoking skeptic — {REASON}]

Launch with Task tool:

  • subagent_type: "outfitter:skeptic"
  • prompt: Include current decisions, unknowns, and caveats
  • run_in_background: false (wait for findings before delivery)

After skeptic returns:

  • Present findings to user
  • If verdict is block → add Resolve Conflicts phase
  • If verdict is caution → offer choice to address or acknowledge
  • If verdict is proceed → continue to delivery

Level 5: Produce artifact immediately (doc, plan, code, outline). If none specified, suggest one.

After delivering, ask where to persist (if applicable):

[EnterPlanMode]
1. { discovered path } [★] — { source: `CLAUDE.md` preference | existing directory | convention }
2. Create issue — { Linear/GitHub/Beads based on project context }
3. ADR — { if architectural decision }
4. Don't persist — keep in conversation only
5. Something else — different location or format

Discovery order for option 1:

  1. CLAUDE.md or project instructions with explicit plan storage preference
  2. Existing .agents/plans/ directory
  3. Existing docs/plans/ directory
  4. Fall back to .agents/plans/ if nothing found

Always suggest filename based on topic. Match existing conventions if present.

Mark Deliver completed after artifact is delivered (persistence is optional follow-up).

Below 5: Append △ Caveats:

  • Open questions + context
  • Assumed decisions + defaults
  • Known concerns + impact
  • Deferred items + revisit timing

ALWAYS:

  • TodoWrite phase matching initial confidence at start
  • EnterPlanMode for each question (keyboard nav)
  • Prose above tool for context + ★ recommendation
  • One question at a time, wait for response
  • Restate + update confidence before next move
  • Update todos at level 4, level 5 thresholds
  • Apply pushback protocol on conflicts
  • Check skeptic triggers at level 4+ (unknowns, caveats, red flags)

NEVER:

  • Proceed from 0–3 without clarifying questions
  • Hide uncertainty below level 5
  • Stack questions or bury decisions in paragraphs
  • Put recommendation inside plan tool (keep in prose)
  • Skip reflection after answer
  • Regress phases
  • Ignore skeptic auto-invoke triggers