Validate Plan with Critical Questions

VerifiedSafe

Interviews the user with critical questions to validate assumptions, confirm decisions, and surface potential issues in an implementation plan before coding begins. Reads plan files, extracts topics like architecture or risks, and presents concrete questions with options to help the user refine their plan.

Sby Skills Guide Bot
DevelopmentIntermediate
806/2/2026
Claude Code
#plan-validation#critical-questions#assumptions-check#risk-analysis#planning

Recommended for

Our review

This skill interviews the user with critical questions to validate assumptions and surface issues in an implementation plan before coding begins.

Strengths

  • Reduces risk by uncovering flaws early
  • Encourages deep thinking on architectural decisions
  • Documents answers directly in the plan for traceability
  • Adapts question count based on configuration

Limitations

  • Does not modify phase files, only the main plan
  • Relies on quality of automatically generated questions
  • May delay start if too many questions are asked
When to use it

Use this skill after drafting a detailed implementation plan and before starting coding, to solidify decisions and identify hidden risks.

When not to use it

Avoid this skill for very simple or well-understood tasks, or when the plan has already been validated by human review and time is critical.

Security analysis

Safe
Quality score90/100

This skill only uses safe tools (Read, Glob, Grep, TaskCreate, AskUserQuestion) to read plan files and interview the user, with no destructive or exfiltrating actions.

No concerns found

Examples

Validate current plan
Validate the current plan with critical questions about assumptions and risks.
Interview on plan decisions
Interview me on the plan decisions and tradeoffs before we start coding.
Check plan for issues
Run plan validation to surface potential issues and confirm our approach.

name: plan-validate version: 1.0.0 description: '[Planning] Validate plan with critical questions interview' allowed-tools: Read, Glob, Grep, TaskCreate, AskUserQuestion

[IMPORTANT] Use TaskCreate to break ALL work into small tasks BEFORE starting — including tasks for each file read. This prevents context loss from long files. For simple tasks, AI MUST ask user whether to skip.

Prerequisites: MUST READ .claude/skills/shared/understand-code-first-protocol.md before executing.

External Memory: For complex or lengthy work (research, analysis, scan, review), write intermediate findings and final results to a report file in plans/reports/ — prevents context loss and serves as deliverable.

Evidence Gate: MANDATORY IMPORTANT MUST — every claim, finding, and recommendation requires file:line proof or traced evidence with confidence percentage (>80% to act, <80% must verify first).

Quick Summary

Goal: Interview the user with critical questions to validate assumptions and surface issues in a plan before coding begins.

Workflow:

  1. Read Plan — Parse plan.md and phase files for decisions, assumptions, risks
  2. Extract Topics — Scan for architecture, assumptions, tradeoffs, risks, scope keywords
  3. Generate Questions — Formulate concrete questions with 2-4 options each
  4. Interview User — Present questions using configured count range
  5. Document Answers — Add Validation Summary section to plan.md

Key Rules:

  • Only ask about genuine decision points; don't manufacture artificial choices
  • Prioritize questions that could change implementation significantly
  • Do NOT modify phase files; just document what needs updating

Be skeptical. Apply critical thinking, sequential thinking. Every claim needs traced proof, confidence percentages (Idea should be more than 80%).

Your mission

Interview the user with critical questions to validate assumptions, confirm decisions, and surface potential issues in an implementation plan before coding begins.

Plan Resolution

  1. If $ARGUMENTS provided -> Use that path
  2. Else check ## Plan Context section -> Use active plan path
  3. If no plan found -> Ask user to specify path or run /plan-hard first

Configuration (from injected context)

Check ## Plan Context section for validation settings:

  • mode - Controls auto/prompt/off behavior
  • questions - Range like 3-8 (min-max)

These values are automatically injected from user config. Use them as constraints.

Workflow

Step 1: Read Plan Files

Read the plan directory:

  • plan.md - Overview and phases list
  • phase-*.md - All phase files
  • Look for decision points, assumptions, risks, tradeoffs

Step 2: Extract Question Topics

Scan plan content for:

| Category | Keywords to detect | | ---------------- | ------------------------------------------------------------------------------------------------------- | | Architecture | "approach", "pattern", "design", "structure", "database", "API" | | Assumptions | "assume", "expect", "should", "will", "must", "default" | | Tradeoffs | "tradeoff", "vs", "alternative", "option", "choice", "either/or" | | Risks | "risk", "might", "could fail", "dependency", "blocker", "concern" | | Scope | "phase", "MVP", "future", "out of scope", "nice to have" | | New Tech/Lib | "install", "add package", "new dependency", "npm install", "dotnet add", framework names not in project |

Step 3: Generate Questions

For each detected topic, formulate a concrete question:

Question format rules:

  • Each question must have 2-4 concrete options
  • Mark recommended option with "(Recommended)" suffix
  • Include "Other" option is automatic - don't add it
  • Questions should surface implicit decisions

Example questions:

Category: Architecture
Question: "How should the validation results be persisted?"
Options:
1. Save to plan.md frontmatter (Recommended) - Updates existing plan
2. Create validation-answers.md - Separate file for answers
3. Don't persist - Ephemeral validation only
Category: Assumptions
Question: "The plan assumes API rate limiting is not needed. Is this correct?"
Options:
1. Yes, rate limiting not needed for MVP
2. No, add basic rate limiting now (Recommended)
3. Defer to Phase 2

Step 4: Interview User

Use AskUserQuestion tool to present questions.

Rules:

  • Use question count from ## Plan Context -> Validation: mode=X, questions=MIN-MAX
  • Group related questions when possible (max 4 questions per tool call)
  • Focus on: assumptions, risks, tradeoffs, architecture

Step 5: Document Answers

After collecting answers, update the plan:

  1. Add ## Validation Summary section to plan.md:
## Validation Summary

**Validated:** {date}
**Questions asked:** {count}

### Confirmed Decisions

- {decision 1}: {user choice}
- {decision 2}: {user choice}

### Action Items

- [ ] {any changes needed based on answers}
  1. If answers require plan changes, note them but do not modify phase files - just document what needs updating.

Output

After validation completes, provide summary:

  • Number of questions asked
  • Key decisions confirmed
  • Any items flagged for plan revision
  • Recommendation: proceed to implementation or revise plan first

IMPORTANT Task Planning Notes (MUST FOLLOW)

  • Always plan and break work into many small todo tasks using TaskCreate
  • Always add a final review todo task to verify work quality and identify fixes/enhancements
  • MANDATORY FINAL TASKS: After creating all planning todo tasks, ALWAYS add these two final tasks:
    1. Task: "Run /plan-validate" — Trigger /plan-validate skill to interview the user with critical questions and validate plan assumptions
    2. Task: "Run /plan-review" — Trigger /plan-review skill to auto-review plan for validity, correctness, and best practices

Important Notes

IMPORTANT: Only ask questions about genuine decision points - don't manufacture artificial choices. IMPORTANT: If plan is simple with few decisions, it's okay to ask fewer than min questions. IMPORTANT: Prioritize questions that could change implementation significantly. MANDATORY IMPORTANT MUST If plan introduces new tech/packages/libraries, ask user: "Plan uses {lib}. Were alternatives evaluated? Confirm choice or research more?"


Next Steps

MANDATORY IMPORTANT MUST after completing this skill, use AskUserQuestion to recommend:

  • "/cook (Recommended)" — Begin implementation with validated plan
  • "/refine" — If plan needs PBI refinement first
  • "Skip, continue manually" — user decides

Closing Reminders

MANDATORY IMPORTANT MUST break work into small todo tasks using TaskCreate BEFORE starting. MANDATORY IMPORTANT MUST validate decisions with user via AskUserQuestion — never auto-decide. MANDATORY IMPORTANT MUST add a final review todo task to verify work quality.

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