Planning With Files
Organize complex projects with persistent markdown files tracking progress and findings
What You Can Do
You can systematically plan and execute complex projects by creating a persistent file-based working memory that survives context resets. Claude maintains three core files (task_plan.md for phases, findings.md for discoveries, progress.md for session logs) that keep your project organized, prevent information loss, and enable automatic recovery after session breaks or /clear commands.
Features
Break projects into phases with clear progress markers (not_started → in_progress → complete)
Capture research discoveries and key information that would otherwise be lost in context
Document test results, errors, and decisions in real time for accountability and learning
Resume complex work seamlessly after context resets or session interruptions
Log failures and mutations to prevent repeating the same mistakes
Record the reasoning behind major choices for future reference
Manage projects requiring 5+ tool calls with clear handoffs between phases
Example Output
Project: API Integration Sprint
task_plan.md output:
## Phase 1: Research & Requirements
- Status: complete
- Endpoints identified: 3 REST, 2 GraphQL
- Auth method: OAuth 2.0
## Phase 2: Schema Design
- Status: in_progress
- Data models drafted
- Validation rules: TBD
findings.md output:
## Key Discoveries
- API rate limit: 100 req/min (discovered during testing)
- Webhook support available (not in docs)
- Pagination required for results >50 items
progress.md output:
## Session 2 (Dec 12)
- ✓ Connected to API sandbox
- ✗ First auth attempt failed (wrong scope)
- ✓ Retry with updated permissions successful
- Test queries executed: 12
What's Included
- SKILL.md instruction file with core principles and critical rules:
- task_plan.md template with phase structure and progress tracking:
- findings.md template for capturing discoveries and research:
- progress.md template for session logs and test results:
- Error tracking checklist to prevent repeating failures:
Who It's For
- Project managers — Coordinate multi-phase initiatives with transparent progress tracking
- Research specialists — Organize findings and prevent information loss across long investigations
- Product managers — Plan feature rollouts with documented decisions and phase management
- Business analysts — Break down complex requirements into actionable, trackable phases
- Operations teams — Manage multi-step processes with persistent session recovery
Best For
- Multi-phase projects requiring 5+ steps or tool calls
- Research tasks involving multiple discoveries to synthesize
- Complex problem-solving requiring iteration and error tracking
- Long-running work that spans multiple sessions
- Projects requiring decision documentation and audit trails
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