Workflow Planning Skill - Quick Reference

This skill enables structured, systematic development workflows. The assistant should apply these patterns when users need to break down complex projects, create implementation plans, or execute multi-step development tasks with clear checkpoints.

Inspired by: Obra Superpowers patterns for structured agent workflows.

Quick Reference

/brainstorm

/write-plan

/execute-plan

/checkpoint

/summarize

When to Use This Skill

The assistant should invoke this skill when a user requests:

• Break down a complex feature into steps
• Create an implementation plan
• Brainstorm approaches to a problem
• Execute a multi-step development task
• Track progress on a project
• Review and adjust mid-implementation

The Three-Phase Workflow

Phase 1: Brainstorm

Purpose: Explore the problem space and generate potential solutions.

/brainstorm [topic or problem]

OUTPUT:
1. Problem Understanding
   - What are we solving?
   - Who is affected?
   - What are the constraints?

2. Potential Approaches (3-5)
   - Approach A: [description, pros, cons]
   - Approach B: [description, pros, cons]
   - Approach C: [description, pros, cons]

3. Questions to Resolve
   - [List of unknowns needing clarification]

4. Recommended Approach
   - [Selected approach with justification]

Phase 2: Write Plan

Purpose: Create a detailed, actionable implementation plan.

/write-plan [feature or task]

OUTPUT:
## Implementation Plan: [Feature Name]

### Goal
[Single sentence describing the outcome]

### Success Criteria
- [ ] Criterion 1
- [ ] Criterion 2
- [ ] Criterion 3

### Steps (with estimates)

#### Step 1: [Name] (~Xh)
- What: [specific actions]
- Files: [files to modify/create]
- Dependencies: [what must exist first]
- Verification: [how to confirm done]

#### Step 2: [Name] (~Xh)
...

### Risks & Mitigations
| Risk | Likelihood | Impact | Mitigation |
|------|-----------|--------|------------|
| Risk 1 | Medium | High | Plan B if... |

### Open Questions
- [Questions to resolve before starting]

Phase 3: Execute Plan

Purpose: Implement the plan systematically with checkpoints.

/execute-plan [plan reference]

EXECUTION PATTERN:
1. Load the plan
2. For each step:
   a. Announce: "Starting Step X: [name]"
   b. Execute actions
   c. Verify completion
   d. Report: "Step X complete. [brief summary]"
3. After completion:
   a. Run all verification criteria
   b. Report final status

Structured Patterns

Hypothesis-Driven Development

PATTERN: Test assumptions before committing

Before implementing:
1. State hypothesis: "If we [action], then [expected outcome]"
2. Define experiment: "To test this, we will [minimal test]"
3. Execute experiment
4. Evaluate: "Hypothesis confirmed/rejected because [evidence]"
5. Proceed or pivot based on result

Incremental Implementation

PATTERN: Build in verifiable increments

For complex features:
1. Identify smallest testable unit
2. Implement and verify
3. Expand scope incrementally
4. Verify at each expansion
5. Integrate and verify whole

Example:
Feature: User authentication
- Increment 1: Basic login form (no backend)
- Increment 2: API endpoint (hardcoded response)
- Increment 3: Database integration
- Increment 4: Session management
- Increment 5: Password reset flow

Progress Tracking

PATTERN: Maintain visible progress

After each action:
[X] Step 1: Create database schema
[X] Step 2: Implement API endpoints
[IN PROGRESS] Step 3: Add frontend form
[ ] Step 4: Write tests
[ ] Step 5: Deploy to staging

Current: Step 3 of 5 (60% complete)
Blockers: None
Next: Complete form validation

Work in Progress (WIP) Limits

PATTERN: Limit concurrent work to improve flow

WIP limits restrict maximum items in each workflow stage.
Benefits: Makes blockers visible, reduces context switching,
often increases throughput.

RECOMMENDED LIMITS:
| Level | Limit | Rationale |
|-------|-------|-----------|
| Individual | 2-3 tasks | Minimize context switching |
| Team (stories) | Team size + 1 | Allow pairing without blocking |
| In Progress column | 3-5 items | Force completion before starting |
| Code Review | 2-3 PRs | Prevent review bottleneck |

SETTING WIP LIMITS:
1. Start with team size + 1
2. Monitor for 2-4 weeks
3. If limits never reached -> lower them
4. If constantly blocked -> investigate bottleneck, don't raise limit
5. Adjust based on actual flow data

WHEN TO VIOLATE (thoughtfully):
- Emergency production fix
- Unblocking another team
- Document the exception and review in retro

Session Management

Starting a Session

Session initialized.
- Project: [name]
- Goal: [today's objective]
- Context loaded: [files, previous decisions]
- Plan status: [steps remaining]

Ready to continue from: [last checkpoint]

Ending a Session

/summarize

OUTPUT:
## Session Summary

### Completed
- [List of completed items]

### In Progress
- [Current state of incomplete work]

### Decisions Made
- [Key decisions with rationale]

### Next Session
- [ ] [First task for next time]
- [ ] [Second task]

### Context to Preserve
[Critical information for continuity]

Decision Framework

When faced with choices:

1. State the decision clearly
2. List options (2-4)
3. For each option:
   - Pros
   - Cons
   - Effort estimate
   - Risk level
4. Recommendation with justification
5. Reversibility assessment

Example:
Decision: How to implement authentication?

| Option | Pros | Cons | Effort | Risk |
|--------|------|------|--------|------|
| JWT | Stateless, scalable | Token management | 2 days | Low |
| Sessions | Simple, secure | Server state | 1 day | Low |
| OAuth only | No passwords | External dependency | 3 days | Medium |

Recommendation: Sessions for MVP, plan JWT migration for scale.

Integration with Other Skills

With Testing Skill

/write-plan with TDD:

Step 1: Write failing test
Step 2: Implement minimal code
Step 3: Verify test passes
Step 4: Refactor
Step 5: Add edge case tests

With Architecture Skill

/brainstorm system design:

1. Requirements clarification
2. Component identification
3. Interface definition
4. Data flow mapping
5. Implementation plan

Definition of Ready / Done (DoR/DoD)

assets/template-dor-dod.md - Checklists for work readiness and completion.

assets/template-work-item-ticket.md - Ticket template with DoR/DoD and testable acceptance criteria.

Key Sections

• Definition of Ready - User story, bug, technical task checklists
• Definition of Done - Feature, bug fix, spike completion criteria
• Acceptance Criteria Templates - Gherkin (Given/When/Then), bullet list, rule-based
• Estimation Guidelines - Story point reference scale (1-21+), slicing strategies
• Planning Levels - Roadmap -> Milestone -> Sprint -> Task hierarchy
• Cross-Functional Coordination - RACI matrix, handoff checklists

Do / Avoid

GOOD: Do

• Check DoR before pulling work into sprint
• Verify DoD before marking complete
• Size stories using reference scale
• Slice large stories (>8 points)
• Document acceptance criteria upfront
• Include risk buffer in estimates
• Coordinate handoffs explicitly

BAD: Avoid

• Starting work without clear acceptance criteria
• Declaring "done" without testing
• Estimating without understanding scope
• Working on stories too big to finish in sprint
• Skipping code review "to save time"
• Deploying without staging verification
• Assuming handoffs happen automatically

Anti-Patterns

Optional: AI/Automation

Note: AI can assist but should not replace human judgment on priorities and acceptance.

• Generate acceptance criteria - Draft from story description (needs review)
• Suggest story slicing - Based on complexity analysis
• Dependency mapping - Identify blocking relationships
• AI-augmented planning - Use LLMs to draft plans, but validate assumptions

AI-Assisted Planning Best Practices

1. Planning first - Create a plan before coding
2. Scope management - Keep tasks small and verifiable
3. Iterative steps - Ship in increments with checkpoints
4. Human oversight - Validate assumptions and outputs (tests, logs, metrics)

Bounded Claims

• AI-generated acceptance criteria need human review
• Story point estimates require team calibration
• Dependency mapping suggestions need validation
• AI impact on delivery stability requires monitoring

Navigation

Resources

• references/planning-templates.md - Plan templates for common scenarios
• references/session-patterns.md - Multi-session project management
• references/flow-metrics.md - DORA metrics, WIP limits, flow optimization
• assets/template-dor-dod.md - DoR/DoD checklists, estimation, cross-functional coordination
• assets/template-work-item-ticket.md - Work item ticket template (DoR/DoD + acceptance criteria)
• data/sources.json - Workflow methodology references

Related Skills

• ../software-architecture-design/SKILL.md - System design planning
• ../docs-ai-prd/SKILL.md - Requirements to plan conversion
• ../qa-testing-strategy/SKILL.md - TDD workflow integration
• ../qa-debugging/SKILL.md - Systematic debugging plans