Planning Document Generator Skill

Purpose

Generate structured assessment documents from JSON configuration. Converts project planning data into markdown assessment reports with purpose, stakeholder, and scope analysis plus a GO/NO-GO decision framework.

When to Use

• Creating project assessment documents
• Generating planning documentation from structured data
• Building evaluation reports with decision matrices
• Documenting project vision and scope
• Creating stakeholder alignment assessments
• Generating baseline project documentation

Input: JSON Format

The skill expects JSON input with the following structure:

{
  "project_name": "Project Name",
  "date": "2025-11-03",
  "why": {
    "exists": "Why does this project exist?",
    "problem": "What problem does it solve?",
    "vision": "What is the desired outcome?"
  },
  "who": {
    "stakeholders": "List of key stakeholders",
    "decision_makers": "Who decides",
    "executors": "Who does the work",
    "concerns": "Their priorities and concerns"
  },
  "what": {
    "building": "What are we building/changing?",
    "features": "Key features and components",
    "out_of_scope": "What is out of scope",
    "success_criteria": "Definition of success"
  },
  "go_no_go": {
    "purpose_clarity": "✓|⚠|✗",
    "stakeholder_alignment": "✓|⚠|✗",
    "scope_definition": "✓|⚠|✗",
    "resource_availability": "✓|⚠|✗",
    "timeline_feasibility": "✓|⚠|✗",
    "risk_assessment": "✓|⚠|✗",
    "success_metrics": "✓|⚠|✗"
  },
  "decision": "GO|CONDITIONAL|NO-GO",
  "rationale": "Explanation of decision"
}

Template Filling Process

1. Load templates/assessment-template.md
2. Replace all {PLACEHOLDER} values with JSON data
3. Calculate coverage: Count non-empty answers ÷ 17 questions
4. Insert status indicators (✓/⚠/✗) from GO/NO-GO section
5. Generate markdown with formatted decision matrix
6. Validate all sections populated with content (no {ANSWER} remaining)

Coverage Calculation

Total question count: 17

Breakdown:

• WHY section: 3 questions
• WHO section: 4 questions
• WHAT section: 4 questions
• GO/NO-GO section: 7 assessment items
• Other: 1 additional (missing info summary)

Formula:

Coverage = (Number of answered/populated fields ÷ 17) × 100
Percentage = Round to nearest whole number

Output Location

Generated documents save to:

~/docs/planning/{project_slug}/assessment-{date}.md

Example:

~/docs/planning/project-name/assessment-2025-11-03.md

Workflow

JSON Input
    ↓
Load Template
    ↓
Replace Placeholders
    ↓
Calculate Coverage
    ↓
Format Decision Matrix
    ↓
Validate Completeness
    ↓
Write to ~/docs/planning/
    ↓
Markdown Output

Key Features

Status Indicators

• ✓ Green: Ready to proceed
• ⚠ Yellow: Proceed with caution / clarification needed
• ✗ Red: Blocker / do not proceed

Decision Framework

• GO: All indicators green, proceed immediately
• CONDITIONAL GO: Some yellow flags, proceed with mitigation
• NO-GO: Red flags present, do not proceed without resolution

Coverage Tracking

Automatically calculates and displays:

• Number of questions answered (X/17)
• Percentage coverage
• List of missing information

Best Practices

1. Complete All Fields: Aim for 100% coverage (17/17)
2. Be Specific: Use concrete details, not generic placeholders
3. Stakeholder Buy-in: Ensure WHO section reflects actual decision-makers
4. Realistic Assessment: Be honest in GO/NO-GO evaluation
5. Document Decisions: Clear rationale essential for tracking

Example Usage

# Command-line usage
planning-doc-generator \
  --input project-plan.json \
  --output ~/docs/planning/myproject/

# Result
~/docs/planning/myproject/assessment-2025-11-03.md

Integration Points

Input Sources

• Project planning worksheets (converted to JSON)
• Kickoff meeting notes (structured into JSON)
• Requirements documents (parsed to JSON format)
• Stakeholder surveys (aggregated to JSON)

Output Consumers

• Project stakeholders (for review/approval)
• Project managers (for tracking)
• Decision makers (for GO/NO-GO calls)
• Documentation archives (for reference)

Validation Rules

Before writing output file:

• All {PLACEHOLDER} values replaced
• No {ANSWER} tokens remaining
• Project name populated
• Date populated (YYYY-MM-DD format)
• Decision field contains valid value (GO, CONDITIONAL, NO-GO)
• Coverage calculated and accurate

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Version: 1.0.0 Created: 2025-11-03 Scope: Global utility skill