Building a Work Plan

Overview

This skill orchestrates the end-to-end process of converting a design document into an executable work plan. It coordinates branch setup, codebase investigation, milestone-by-milestone planning, and handoff to execution. Think of it as the "conductor" that invokes sub-skills and agents in the right order.

Required Sub-Skills

Load these during execution:

| Skill | Purpose | When Loaded | |-------|---------|-------------| | writing-a-work-plan | Task decomposition patterns, templates | Phase 2 | | writing-code | Engineering principles (via writing-a-work-plan) | Phase 2 |

Entry Point

When the user invokes /build-work-plan:

1. Announce: "I'm using the building-a-work-plan skill to create a work plan from your design document."

2. Get design document path:

   • If user provided a path, use it
   • If not, use AskUserQuestion to request the path
   • Never guess the path

3. Choose review mode (MANDATORY):

   STOP. You MUST get user preference before creating orchestration tasks.

   Use AskUserQuestion with these options:

   • Interactive (Recommended): Plan one milestone, get approval, proceed. Catches errors early.
   • Batch: Plan all milestones, then review all. Faster but riskier.

   Record the user's choice. This determines behavior in Phase 2 and Phase 4.

4. Create orchestration tasks (see Task Tracking section)

5. Proceed through phases

Task Tracking

Create these tasks at the start of each session. Update status as you progress.

◻ #1 Setup: Confirm design doc and optional branch setup
◻ #2 Investigate: Codebase testing patterns
◻ #3 Investigate: Design assumptions verification
◻ #4 Plan: Write milestone tasks (one sub-task per milestone)
◻ #5 Verify: Post-planning codebase check
◻ #6 Review: Code review of plan
◻ #7 Approve: User approval
◻ #8 Write: Save plan to disk
◻ #9 Handoff: Execution instructions

Dependencies:

• #2 blocked by #1
• #3 blocked by #2
• #4 blocked by #3
• #5 blocked by #4
• #6 blocked by #5
• #7 blocked by #6
• #8 blocked by #7
• #9 blocked by #8

Use TaskCreate and TaskUpdate to manage these. Mark each task in_progress when starting, completed when done.

Phases

Phase 0: Setup (Task #1)

Step 1: Confirm design document

Read the design document. Verify it contains:

• [ ] Fleshed-out milestones (job stories, descriptions, AC, demos)
• [ ] Milestone count ≤ 8

If milestones are vague or missing AC, stop and suggest running /start-milestone-review first.

Step 2: Optional branch setup

Ask the user:

Do you need to set up a branch for this work?
- Yes, create a new branch
- No, I'm already on the correct branch

If yes:

1. Determine base branch (main or master)
2. Generate branch name from design doc title (e.g., feat/trackman-scraper)
3. Create and checkout branch: git checkout -b <branch-name>
4. Confirm branch created

Mark Task #1 complete.

Phase 1: Codebase Investigation (Tasks #2, #3)

Task #2: Testing patterns

Dispatch codebase-investigator agent:

Investigate the testing patterns in this codebase:
- How are tests structured? (tests/, test/, colocated?)
- What testing framework is used? (pytest, jest, etc.)
- What mocking patterns exist?
- What fixtures are available?
- Any test utilities or helpers?

Report findings in a structured format.

Document findings. Mark Task #2 complete.

Task #3: Design assumptions (sequential after #2)

Dispatch codebase-investigator agent:

Verify these design assumptions against the current codebase:

Design doc: [path]
Milestones: [list milestone titles]

Check:
- Do files exist where the design expects them?
- Do expected features/dependencies exist?
- Is there drift between design doc and current code?
- What naming conventions should we follow?

Report any mismatches or concerns.

Document findings. Mark Task #3 complete.

Phase 2: Milestone Planning (Task #4)

CHECKPOINT: Verify sub-skill is loaded.

Before processing any milestone, confirm you have loaded writing-a-work-plan skill. If you have not loaded it, STOP and load it now using the Skill tool.

This sub-skill provides:

• Milestone plan header template (Context, Codebase Verification, References)
• Task templates by type (Infrastructure, Functionality, Integration)
• TDD-aligned implementation step patterns

Load sub-skill: Activate writing-a-work-plan skill.

Process each milestone following the writing-a-work-plan Core Pattern:

For each milestone M:

1. Create sub-task: "Plan: Milestone M - [title]"

2. Read milestone from design doc

3. Write complete milestone plan header (see writing-a-work-plan Document Format)

4. Classify each AC (infrastructure, functionality, integration)

5. Create scaffold task if needed

6. Create one task per AC with implementation steps

7. If Interactive mode: Use AskUserQuestion to get approval:

   • Approve: Milestone plan looks good, proceed to next milestone
   • Revise: I have feedback on specific tasks (user provides details via "Other")

   Do not proceed until user approves or revisions are complete.

8. Write milestone to disk immediately after approval (enables session recovery)

9. If Batch mode: Continue to next milestone

10. Mark sub-task complete

Mark Task #4 complete when all milestones are planned.

Phase 3: Post-Planning Verification (Task #5)

Dispatch codebase-investigator agent:

Verify the planned tasks are implementable:

Work plan location: [path]

Check:
- Do target directories exist (or can be created)?
- Are import paths valid?
- Any conflicts with existing code?
- Are test file locations correct?

Report any issues that would block implementation.

If issues found:

• Present to user
• Update tasks to match reality, or
• Flag as known issues in the plan

Mark Task #5 complete.

Phase 4: Code Review (Task #6)

This phase is MANDATORY. Do not skip code review.

Even for "simple" plans, code review catches:

• Missing tasks for AC
• Vague verification steps that cause confusion during implementation
• Inconsistent commit message formats
• Dependency ordering issues

Dispatch code-reviewer agent over all milestone plan files:

Review these work plan files for quality:

Files: [list of milestone_##.md files]

Check:
- All AC have corresponding tasks
- Tasks include concrete test code where applicable
- Verification steps are explicit
- Commit messages follow conventions
- Dependencies are noted
- No ambiguous or vague steps

Report issues by file and task number.

Handle review results based on review mode (chosen in Entry Point step 3):

• Interactive mode: Present issues to user; let user decide what to fix
• Batch mode: Automatically fix issues; user sees clean plan

Verification: Before marking Task #6 complete, confirm:

• [ ] Code review agent was dispatched
• [ ] All reported issues were addressed (fixed or user-approved as-is)
• [ ] Results were presented to user

Mark Task #6 complete.

Phase 5: User Approval (Task #7)

Present the complete work plan summary:

## Work Plan Summary

**Design doc**: [path]
**Plan location**: [path]
**Milestones**: [count]

| Milestone | Tasks | Type Breakdown |
|-----------|-------|----------------|
| M1: [title] | N tasks | X infra, Y func, Z integ |
| M2: [title] | N tasks | ... |
| ... | ... | ... |

**Total tasks**: [count]

**Codebase verification**: [status]
**Code review**: [status]

Ready to write to disk?

Get explicit approval. Mark Task #7 complete.

Phase 6: Write to Disk (Task #8)

Create directory and files using this EXACT structure:

docs/work-plans/YYYY-MM-DD-<plan-name>/
├── milestone_01.md
├── milestone_02.md
├── ...
└── milestone_NN.md

Concrete example (for a plan named "golf-data-loader" on 2026-01-15):

docs/work-plans/2026-01-15-golf-data-loader/
├── milestone_01.md
├── milestone_02.md
├── milestone_03.md

Naming rules:

• Directory: YYYY-MM-DD-<plan-name> where plan-name is lowercase, hyphenated
• Files: milestone_01.md, milestone_02.md, etc. (zero-padded two digits)
• NOT: m1-*.md, M1_*.md, milestone-1.md, or any other variant

Verification (REQUIRED before marking complete):

ls -la docs/work-plans/YYYY-MM-DD-<plan-name>/

Confirm output shows:

• Directory name matches YYYY-MM-DD-<plan-name> format
• All files are named milestone_##.md

Mark Task #8 complete only after verification passes.

Phase 7: Execution Handoff (Task #9)

Capture absolute paths:

git rev-parse --show-toplevel  # Working root

Present handoff instructions:

## Work Plan Complete

Your work plan is ready at:
`[absolute-path-to-plan-directory]`

### Next Steps

To execute this work plan:

/execute-work-plan [absolute-path-to-plan-directory]

This will:
1. Read milestones just-in-time (one at a time)
2. Dispatch `code-worker` agents for each task
3. Run code review once per milestone
4. Fix all issues before proceeding to next milestone
5. Provide a full implementation report when complete

### To Resume Later

If you need to resume work on this plan in a new session:
1. Run `/clear` to reset context
2. Run `/execute-work-plan [plan-directory-path]`
3. The skill will detect progress and resume from the next incomplete task

### Files Created

[List all milestone_##.md files with paths]

Mark Task #9 complete.

Resumption

If the user returns to continue a work plan:

1. Ask for the plan directory path
2. Read existing milestone files
3. Identify which milestones are complete vs pending
4. Resume from the next pending milestone

Common Mistakes

| Mistake | Why It Fails | Correct Approach | |---------|--------------|------------------| | Guessing design doc path | Wrong file, wasted effort | Always ask if not provided | | Skipping review mode choice | User loses control over workflow | AskUserQuestion at session start | | Skipping codebase investigation | Tasks may not be implementable | Always investigate before planning | | Not tracking orchestration tasks | Lose progress on interruption | Create tasks at session start | | Relative paths in handoff | Paths break across sessions | Always use absolute paths | | Batch planning all milestones | Early mistakes compound | Interactive milestone-by-milestone | | Skipping code review phase | Plan quality issues compound during implementation | Code review is MANDATORY | | Wrong file naming (m1-*.md) | Breaks execution skill expectations | Use milestone_01.md format | | Incomplete milestone headers | Implementers lack context | All header fields are required |

Anti-Rationalizations

• "I know where the design doc is" — Ask anyway. Confirmation prevents errors.
• "Codebase investigation is slow" — It's faster than planning tasks for nonexistent files.
• "Task tracking is overhead" — It's insurance against interruption. Do it.
• "The user knows the paths" — Capture absolute paths explicitly. Context resets.
• "Batch mode is faster" — User loses opportunity to catch early mistakes. Compounding errors cost more than time saved. Ask for their preference.
• "Code review is overkill for a plan" — Plans with issues compound during implementation. A 10-minute review saves hours of debugging.
• "The user will notice the file naming" — They won't until the execution skill fails. Follow the spec exactly.
• "The milestone header is just boilerplate" — It's context for the implementer (human or LLM). Missing context means wrong assumptions.

Summary

1. Announce the skill. User knows what's happening.
2. Create orchestration tasks. Track progress through phases.
3. Investigate before planning. Codebase reality grounds the plan.
4. Interactive milestone review. Approve each before proceeding.
5. Capture absolute paths. Handoff survives context reset.
6. Execution is future work. Plan is the deliverable for now.