Structured Planning

Structured Planning Skill

Industry-standard planning workflows that guide you through proper specification before implementation - with dynamic question depth based on complexity.

Overview

This skill provides guided, conversational planning for three task types:

Key Behaviors:

• Auto-detects mode from your request (you confirm or override)
• Dynamic depth - questions deepen when your answers indicate complexity
• Full documentation - creates specs that become your source of truth
• Orchestration handoff - planning feeds directly into /orchestration:* commands

When to Use This Skill

Ideal Use Cases

Trigger Phrases

The system auto-detects planning needs from phrases like:

• "I want to build/create/design..."
• "Let's plan out..."
• "I need to add a feature for..."
• "Review/audit/assess my..."
• "Improve/optimize the existing..."

When NOT to Use

Quick Actions

Complete Workflow

┌─────────────────────────────────────────────────────────────────┐
│                   STRUCTURED PLANNING WORKFLOW                   │
├─────────────────────────────────────────────────────────────────┤
│  PHASE 1: MODE DETECTION                                         │
│  └─ System analyzes request                                      │
│     ├─ Suggests: New Design / System Review / Feature            │
│     └─ You confirm or override                                   │
├─────────────────────────────────────────────────────────────────┤
│  PHASE 2: DISCOVERY                                              │
│  └─ Conversational question flow                                 │
│     ├─ Vision & Goals (what, why, for whom)                      │
│     ├─ Scope & Features (must-have, nice-to-have, out-of-scope)  │
│     ├─ Technical Considerations (stack, constraints, integrations)│
│     └─ Dynamic depth: deeper questions when complexity detected  │
├─────────────────────────────────────────────────────────────────┤
│  PHASE 3: SPECIFICATION                                          │
│  └─ Generate documentation                                       │
│     ├─ Draft summary for review                                  │
│     ├─ Iterate based on feedback                                 │
│     └─ Create: .claude/planning/specs/YYYY-MM-DD-{name}.md       │
├─────────────────────────────────────────────────────────────────┤
│  PHASE 4: ORCHESTRATION HANDOFF                                  │
│  └─ Generate execution plan                                      │
│     ├─ Convert spec acceptance criteria to tasks                 │
│     ├─ Create: .claude/orchestration/YYYY-MM-DD-{name}.yaml      │
│     └─ Ready for /orchestration:status, :resume, :commit         │
└─────────────────────────────────────────────────────────────────┘

Components Reference

Commands

Templates

Deterministic Tools

Following the Code Before Prompts pattern, this skill includes TypeScript tools for routine operations.

cd .claude/skills/structured-planning

# Show planning status
npx tsx tools/index.ts status

# Create spec from template
npx tsx tools/index.ts create new "My Project"
npx tsx tools/index.ts create review "System Name"
npx tsx tools/index.ts create feature "Feature Name"

# List existing specs
npx tsx tools/index.ts list

# Validate spec completeness
npx tsx tools/index.ts validate .claude/planning/specs/2026-01-21-my-project.md

# Archive completed spec
npx tsx tools/index.ts archive .claude/planning/specs/2026-01-21-my-project.md

Output Locations

Dynamic Depth System

Questions deepen automatically when your answers indicate complexity:

Complexity Signals

Depth Control

• Default: Auto-calibrates based on your answers
• Quick mode: /plan --depth=minimal skips extended questions
• Thorough mode: /plan --depth=comprehensive asks everything
• Manual: Say "that's enough detail" to move on

Detailed Workflows

New Design Mode

Purpose: Full specification for building something from scratch

Question Categories:

1. Vision: Problem, users, success criteria
2. Scope: Features (must-have, nice-to-have, out-of-scope)
3. Technical: Stack, architecture, integrations
4. Constraints: Timeline, performance, security
5. Risks: What could go wrong, mitigations

Output: Complete design specification with orchestration plan

System Review Mode

Purpose: Assess existing system and create improvement plan

Question Categories:

1. Current State: What exists, what works well
2. Pain Points: Issues, technical debt, friction
3. Desired State: Goals, target architecture
4. Gap Analysis: What needs to change
5. Prioritization: Quick wins vs strategic changes

Output: Review findings document with improvement orchestration

Feature Planning Mode

Purpose: Lighter workflow for adding to existing projects

Question Categories:

1. Feature Scope: What capability, for whom
2. Integration: How it fits with existing code
3. Acceptance: How we know it's done

Output: Feature specification with orchestration tasks

Integration Points

With Orchestration System

Planning creates orchestration automatically:

# Generated orchestration includes:
spec_file: ".claude/planning/specs/2026-01-19-habit-tracker.md"
planning_mode: "new_design"

# Use standard orchestration commands:
/orchestration:status   # See progress
/orchestration:resume   # Continue work
/orchestration:commit   # Link commits to tasks

With Project Lifecycle

For new projects:

1. /plan:new creates specification
2. /new-code-project creates the project
3. Orchestration tracks implementation

With Memory MCP

Planning decisions stored for future reference:

• Decision: {project} Architecture with rationale
• Pattern: {pattern} for reusable patterns

Example Session

User: I want to build a habit tracking application

Claude: I'll help you plan this. Based on your request, I'm suggesting
**New Design** mode for a full planning workflow.

[Confirms mode]

Let me start with some questions about your vision...

**What specific problem are you trying to solve?**
- Who struggles with habits today?
- What makes existing solutions inadequate?

User: People forget to do their habits and lose motivation. Most apps
are too complicated with too many features.

Claude: I notice you mentioned simplicity as important. Let me dig
deeper on the scope...

**What are the absolute must-have features for launch?**

User: Just habit creation, daily check-in, and a streak counter.
Maybe notifications but I'm not sure about that.

Claude: You mentioned uncertainty about notifications. Let me clarify...

**What's your concern about notifications?**
- Technical complexity?
- User experience?
- Platform support?

[Continues with dynamic depth based on answers...]

[After discovery complete:]

Here's your design specification draft:

## Habit Tracker - Design Specification
### Vision: Simple daily habit tracking focused on streaks...

Does this capture your intent? Any adjustments needed?

User: Looks good, let's proceed.

Claude: Created specification at `.claude/planning/specs/2026-01-19-habit-tracker.md`
Created orchestration at `.claude/orchestration/2026-01-19-habit-tracker.yaml`

Run `/orchestration:status` to see your implementation plan.

Troubleshooting

Common Issues

Getting Help

• Review example sessions: .claude/skills/structured-planning/examples/
• Check question bank: .claude/skills/structured-planning/templates/question-bank.yaml

Related Documentation

• Orchestration System - Execution tracking after planning
• PARC Pattern - Quick design review (lighter than full planning)
• Parallel Dev Skill - Autonomous implementation after planning

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