home / skills / dmmulroy / .dotfiles / overseer-plan
This skill converts Markdown planning documents into Overseer tasks and milestones, producing a structured, trackable hierarchy from plans to actionable work.
npx playbooks add skill dmmulroy/.dotfiles --skill overseer-planReview the files below or copy the command above to add this skill to your agents.
---
name: overseer-plan
description: Convert markdown planning documents to Overseer tasks via MCP codemode. Use when converting plans, specs, or design docs to trackable task hierarchies.
license: MIT
metadata:
author: dmmulroy
version: "1.0.0"
---
# Converting Markdown Documents to Overseer Tasks
Use `/overseer-plan` to convert any markdown planning document into trackable Overseer tasks.
## When to Use
- After completing a plan in plan mode
- Converting specs/design docs to implementation tasks
- Creating tasks from roadmap or milestone documents
## Usage
```
/overseer-plan <markdown-file-path>
/overseer-plan <file> --priority 3 # Set priority (1-5)
/overseer-plan <file> --parent <task-id> # Create as child of existing task
```
## What It Does
1. Reads markdown file
2. Extracts title from first `#` heading (strips "Plan: " prefix)
3. Creates Overseer milestone (or child task if `--parent` provided)
4. Analyzes structure for child task breakdown
5. Creates child tasks (depth 1) or subtasks (depth 2) when appropriate
6. Returns task ID and breakdown summary
## Hierarchy Levels
| Depth | Name | Example |
|-------|------|---------|
| 0 | **Milestone** | "Add user authentication system" |
| 1 | **Task** | "Implement JWT middleware" |
| 2 | **Subtask** | "Add token verification function" |
## Breakdown Decision
**Create subtasks when:**
- 3-7 clearly separable work items
- Implementation across multiple files/components
- Clear sequential dependencies
**Keep single milestone when:**
- 1-2 steps only
- Work items tightly coupled
- Plan is exploratory/investigative
## Task Quality Criteria
Every task must be:
- **Atomic**: Single committable unit of work
- **Validated**: Has tests OR explicit acceptance criteria in context ("Done when: ...")
- **Clear**: Technical, specific, imperative verb
Every milestone must:
- **Demoable**: Produces runnable/testable increment
- **Builds on prior**: Can depend on previous milestone's output
## Review Workflow
1. Analyze document → propose breakdown
2. **Invoke Oracle** to review breakdown and suggest improvements
3. Incorporate feedback
4. Create in Overseer (persists to SQLite via MCP)
## After Creating
```javascript
await tasks.get("<id>"); // TaskWithContext (full context + learnings)
await tasks.list({ parentId: "<id>" }); // Task[] (children without context chain)
await tasks.start("<id>"); // Task (VCS required - creates bookmark, records start commit)
await tasks.complete("<id>", { result: "...", learnings: [...] }); // Task (VCS required - commits, bubbles learnings)
```
**VCS Required**: `start` and `complete` require jj or git (fail with `NotARepository` if none found). CRUD operations work without VCS.
**Note**: Priority must be 1-5. Blockers cannot be ancestors or descendants.
## When NOT to Use
- Document incomplete or exploratory
- Content not actionable
- No meaningful planning content
---
## Reading Order
| Task | File |
|------|------|
| Understanding API | @file references/api.md |
| Agent implementation | @file references/implementation.md |
| See examples | @file references/examples.md |
## In This Reference
| File | Purpose |
|------|---------|
| `references/api.md` | Overseer MCP codemode API types/methods |
| `references/implementation.md` | Step-by-step execution instructions for agent |
| `references/examples.md` | Complete worked examples |
This skill converts Markdown planning documents into tracked Overseer tasks using MCP codemode. It reads a plan or spec, extracts the top-level title as a milestone, analyzes heading structure to produce tasks and subtasks, and persists them into Overseer. The output includes created task IDs and a concise breakdown summary for review and iteration.
The skill parses the Markdown file, uses the first H1 (stripping a "Plan: " prefix if present) as the milestone title, and inspects headings and lists to derive child tasks (depth 1) and subtasks (depth 2). It enforces task quality rules (atomic, validated, clear), applies priority and optional parent linking, and calls the Overseer MCP codemode to create records in SQLite. After creation it returns IDs and supports later operations like get, list, start, and complete.
What does the command look like?
/overseer-plan <markdown-file-path> with optional flags like --priority <1-5> and --parent <task-id>.
When will the skill create subtasks instead of tasks?
Subtasks are created for depth-2 items or when 3–7 separable work items, multiple components, or clear sequential dependencies are detected.
Do start and complete work without a VCS?
CRUD operations work without a VCS, but start and complete require a git or jj repository and will fail with NotARepository if none is found.