OAK Strategic Planning Workflow

This skill provides domain expertise for OAK's planning system - creating implementation plans that align with project constitutions, follow OAK file conventions, and integrate with the oak.plan-* command workflow.

OAK Planning System Overview

Command Workflow

/oak.plan-create  →  /oak.plan-research  →  /oak.plan-tasks  →  /oak.plan-implement
        │                    │                     │                     │
        ↓                    ↓                     ↓                     ↓
   plan.md            research/*.md           tasks.md           Implementation
                                                   │
                                                   ↓
                                          /oak.plan-export
                                          (GitHub/ADO issues)

File Structure

oak/
├── constitution.md          # Project standards (required first)
└── plan/
    └── <plan-name>/
        ├── plan.md          # Main plan document
        ├── .manifest.json   # Plan metadata and state
        ├── tasks.md         # Generated task breakdown
        ├── issue/           # Issue context (if issue-based)
        │   ├── summary.md
        │   └── related/
        └── research/        # Research findings
            ├── <topic>.md
            └── research-manifest.yml

When to Use This Skill

Use when you need to:

• Create a new implementation plan (/oak.plan-create)
• Understand OAK's planning conventions and file formats
• Structure development work following OAK patterns
• Ensure plan alignment with project constitution
• Generate well-defined success criteria

Planning Framework (OAK-Specific)

Phase 1: Context Gathering

Before planning, OAK requires:

Source Material

• Issue tracking details (ADO #123, GitHub #42) - fetched automatically
• Stakeholder requirements via clarifying questions
• Related existing features in codebase

Constitution Requirements (from oak/constitution.md)

• Architecture patterns to follow
• Testing requirements (TDD, coverage %)
• Documentation standards
• Code style guidelines

Technical Landscape

• Existing patterns in codebase (explored via /oak.plan-create)
• Similar implementations to reference
• Integration points

Phase 2: Scope Definition

OAK plans require clear boundaries in these sections:

In Scope (## Scope > ### In Scope)

• Core functionality required
• Must-have features
• Required integrations

Out of Scope (## Scope > ### Out of Scope)

• Future enhancements
• Nice-to-have features
• Separate concerns

Assumptions (document in ## Constraints)

• Technical assumptions
• Resource assumptions
• Dependencies on external factors

Phase 3: Risk Assessment

OAK plans include risks in a structured format:

## Risks & Mitigations

| Risk | Impact | Mitigation |
|------|--------|-----------|
| Integration complexity | High | Prototype early, create fallback |
| Skill gaps | Medium | Pair programming, documentation |
| Dependencies | Medium | Buffer time, parallel workstreams |

Phase 4: Research Topics

Identify unknowns for /oak.plan-research:

## Research Topics

- **[Topic Name]**: [What we need to learn]
  - Questions: [Specific questions to answer]
  - Priority: High/Medium/Low

Phase 5: Success Criteria

Define measurable outcomes:

## Success Criteria

- [ ] [Functional criterion - feature works as specified]
- [ ] [Quality criterion - test coverage, performance]
- [ ] [Process criterion - documentation, review]
- [ ] [Constitution compliance - all MUST rules followed]

OAK Plan Document Structure

This is the expected format for oak/plan/<name>/plan.md:

# Plan: [Title]

## Overview
[1-2 paragraph summary of what will be built]

## Goals
- [Goal 1]
- [Goal 2]

## Success Criteria
- [ ] [Criterion 1]
- [ ] [Criterion 2]

## Scope

### In Scope
- [Item 1]

### Out of Scope
- [Item 1]

## Constraints
- [Constraint 1]

## Research Topics
- [Topic 1]: [Why needed]

## Risks & Mitigations
| Risk | Impact | Mitigation |
|------|--------|-----------|
| [Risk] | High/Med/Low | [Strategy] |

## Constitution Compliance
- Architecture: [How plan aligns]
- Testing: [Test strategy per constitution]
- Documentation: [Doc requirements]

Best Practices for OAK Plans

1. Start with the constitution - Read oak/constitution.md first; let project standards guide the plan
2. Use issue context - If issue-driven, leverage fetched acceptance criteria and related issues
3. Identify research topics - Unknowns become research topics for /oak.plan-research
4. Define done clearly - Success criteria should be verifiable
5. Consider testing early - Note constitution's test requirements (TDD vs test-after)
6. Plan for iteration - OAK supports research → tasks → implement cycle

Integration with OAK Commands

Quick Reference

• Plan location: oak/plan/<name>/plan.md
• Constitution: oak/constitution.md (always read first)
• Branch naming: plan/<name> or <issue-id>/<name>
• Research output: oak/plan/<name>/research/<topic>.md
• Tasks output: oak/plan/<name>/tasks.md