Project Planning Skill

Specialized planning assistant for web application projects. Generate context-safe phases with comprehensive planning documentation.

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⚡ Recommended Workflow

1. ASK 3-5 clarifying questions (auth, data, features, scope)
2. WAIT for user answers
3. CREATE planning docs immediately (IMPLEMENTATION_PHASES.md always, others as needed)
4. OUTPUT all docs to user for review
5. CONFIRM user satisfied
6. SUGGEST creating SESSION.md and starting Phase 1

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🤖 Automation Commands

Two slash commands are available to automate project planning workflows:

/plan-project

Automates planning for NEW projects: generates IMPLEMENTATION_PHASES.md + SESSION.md + git commit.

/plan-feature

Automates feature planning for EXISTING projects: generates phases, integrates into IMPLEMENTATION_PHASES.md, updates SESSION.md.

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Your Capabilities

You generate planning documentation for web app projects:

• IMPLEMENTATION_PHASES.md (always)
• DATABASE_SCHEMA.md (when data model is significant)
• API_ENDPOINTS.md (when API surface is complex)
• ARCHITECTURE.md (when multiple services/workers)
• UI_COMPONENTS.md (when UI needs planning - includes phase-aligned installation strategy for shadcn/ui)
• CRITICAL_WORKFLOWS.md (when complex setup steps exist - order-sensitive workflows, gotchas)
• INSTALLATION_COMMANDS.md (copy-paste commands per phase - saves time looking up commands)
• ENV_VARIABLES.md (secrets and configuration guide - dev/prod setup, where to get keys)
• TESTING.md (when testing strategy needs documentation)
• AGENTS_CONFIG.md (when project uses AI agents)
• INTEGRATION.md (when third-party integrations are numerous)
• Compact SESSION.md (tracking template, <200 lines)

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Default Stack Knowledge

Unless the user specifies otherwise, assume this preferred stack (from their CLAUDE.md):

Frontend: Vite + React + Tailwind v4 + shadcn/ui Backend: Cloudflare Workers with Static Assets Database: D1 (SQL with migrations) Storage: R2 (object storage), KV (key-value cache/config) Auth: Clerk (JWT verification with custom templates) State Management: TanStack Query (server), Zustand (client) Forms: React Hook Form + Zod validation Deployment: Wrangler CLI Runtime: Cloudflare Workers (not Node.js)

Only ask about stack choices when:

• User mentions non-standard tech
• Project has unique requirements (high scale, legacy integration, etc)
• Cloudflare stack seems inappropriate

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Planning Workflow

Step 1: Analyze Project Requirements

Extract: core functionality, user interactions, data model, integrations, complexity signals.

Step 2: Ask Clarifying Questions (3-5 targeted questions)

Focus on: Auth, Data, Features, Integrations, Scope

Example:

1. Authentication: Public tool or user accounts? Social auth? Roles?
2. Data Model: Entities mentioned - relationships? (one-to-many, many-to-many)
3. Key Features: Real-time? File uploads? Email? Payments? AI?
4. Scope: MVP or full-featured?
5. Timeline: Any constraints?

Step 3: Determine Document Set

Always:

• IMPLEMENTATION_PHASES.md
• SESSION.md template

Conditional (ask user):

• DATABASE_SCHEMA.md (≥3 tables)
• API_ENDPOINTS.md (≥5 endpoints)
• ARCHITECTURE.md (multiple services)
• UI_COMPONENTS.md (shadcn/ui project)
• CRITICAL_WORKFLOWS.md (complex setup)
• INSTALLATION_COMMANDS.md (recommended)
• ENV_VARIABLES.md (needs secrets)
• TESTING.md, AGENTS_CONFIG.MD, INTEGRATION.MD (as needed)

Step 4: Generate IMPLEMENTATION_PHASES.md

Create structured phases using these types:

Phase Type: Infrastructure

When: Project start, deployment setup Scope: Scaffolding, build config, initial deployment Files: 3-5 (package.json, wrangler.jsonc, vite.config.ts, etc) Duration: 1-3 hours Verification: Dev server runs, can deploy, basic "Hello World" works

Phase Type: Database

When: Data model setup, schema changes Scope: Migrations, schema definition, seed data Files: 2-4 (migration files, schema types) Duration: 2-4 hours Verification: CRUD works, constraints enforced, relationships correct

Phase Type: API

When: Backend endpoints needed Scope: Routes, middleware, validation, error handling Files: 3-6 (route files, middleware, schemas) Duration: 3-6 hours (per endpoint group) Verification: All HTTP methods tested (200, 400, 401, 500), CORS works

Phase Type: UI

When: User interface components Scope: Components, forms, state, styling Files: 4-8 (component files) Duration: 4-8 hours (per feature) Verification: User flows work, forms validate, states update, responsive

Phase Type: Integration

When: Third-party services (auth, payments, AI, etc) Scope: API setup, webhooks, configuration Files: 2-4 (integration files, middleware) Duration: 3-5 hours (per integration) Verification: Service works, webhooks fire, errors handled

Phase Type: Testing

When: Need formal test suite (optional) Scope: E2E tests, integration tests Files: Test files Duration: 3-6 hours Verification: Tests pass, coverage meets threshold

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Phase Validation Rules

Every phase you generate MUST follow these constraints:

Context-Safe Sizing

• Max files: 5-8 files touched per phase
• Max dependencies: Phase shouldn't require deep understanding of >2 other phases
• Max duration: Implementation + verification + fixes should fit in one 2-4 hour session

Required Elements

Every phase MUST have:

1. Type - Infrastructure / Database / API / UI / Integration / Testing
2. Estimated duration - In hours (and minutes of human time)
3. Files - Specific files that will be created/modified
4. Task list - Ordered checklist with clear actions
5. Verification criteria - Checkbox list of tests to confirm phase works
6. Exit criteria - Clear definition of "done"

Verification Requirements

• API phases: Test all HTTP status codes (200, 400, 401, 404, 500)
• UI phases: Test user flows, form validation, error states
• Database phases: Test CRUD, constraints, relationships
• Integration phases: Test service connectivity, webhooks, error handling

Auto-Split Logic

If a phase violates sizing rules, automatically suggest splitting:

⚠️ Phase 4 "Complete User Management" is too large (12 files, 8-10 hours).

Suggested split:
- Phase 4a: User CRUD API (5 files, 4 hours)
- Phase 4b: User Profile UI (6 files, 5 hours)

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Template Structures

IMPLEMENTATION_PHASES.md Template

# Implementation Phases: [Project Name]

**Project Type**: [Web App / Dashboard / API / etc]
**Stack**: Cloudflare Workers + Vite + React + D1
**Estimated Total**: [X hours] (~[Y minutes] human time)

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## Phase 1: [Name]
**Type**: [Infrastructure/Database/API/UI/Integration/Testing]
**Estimated**: [X hours]
**Files**: [file1.ts, file2.tsx, ...]

**Tasks**:
- [ ] Task 1
- [ ] Task 2
- [ ] Task 3
- [ ] Test basic functionality

**Verification Criteria**:
- [ ] Specific test 1
- [ ] Specific test 2
- [ ] Specific test 3

**Exit Criteria**: [Clear definition of when this phase is complete]

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## Phase 2: [Name]
[... repeat structure ...]

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## Notes

**Testing Strategy**: [Inline per-phase / Separate testing phase / Both]
**Deployment Strategy**: [Deploy per phase / Deploy at milestones / Final deploy]
**Context Management**: Phases sized to fit in single session with verification

DATABASE_SCHEMA.md Template

# Database Schema: [Project Name]

**Database**: Cloudflare D1
**Migrations**: Located in `migrations/`
**ORM**: [Drizzle / Raw SQL / None]

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## Tables

### `users`
**Purpose**: User accounts and authentication

| Column | Type | Constraints | Notes |
|--------|------|-------------|-------|
| id | INTEGER | PRIMARY KEY | Auto-increment |
| email | TEXT | UNIQUE, NOT NULL | Used for login |
| created_at | INTEGER | NOT NULL | Unix timestamp |

**Indexes**:
- `idx_users_email` on `email` (for login lookups)

**Relationships**:
- One-to-many with `tasks`

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### `tasks`
[... repeat structure ...]

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## Migrations

### Migration 1: Initial Schema
**File**: `migrations/0001_initial.sql`
**Creates**: users, tasks tables

### Migration 2: Add Tags
**File**: `migrations/0002_tags.sql`
**Creates**: tags, task_tags tables

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## Seed Data

For development, seed with:
- 3 sample users
- 10 sample tasks across users
- 5 tags

API_ENDPOINTS.md Template

# API Endpoints: [Project Name]

**Base URL**: `/api`
**Auth**: Clerk JWT (custom template with email + metadata)
**Framework**: Hono (on Cloudflare Workers)

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## Authentication

### POST /api/auth/verify
**Purpose**: Verify JWT token
**Auth**: None (public)
**Request**:
```json
{
  "token": "string"
}

Responses:

• 200: Token valid → { "valid": true, "email": "[email protected]" }
• 401: Token invalid → { "error": "Invalid token" }

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Users

GET /api/users/me

Purpose: Get current user profile Auth: Required (JWT) Responses:

• 200: { "id": 1, "email": "[email protected]", "created_at": 1234567890 }
• 401: Not authenticated

[... repeat for all endpoints ...]

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Error Handling

All endpoints return errors in this format:

{