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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 1           # Set priority (0-2, 0=highest)
/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

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

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

In This Reference

Weekly Installs

105

Repository

dmmulroy/overseer

GitHub Stars

222

First Seen

Jan 27, 2026

Security Audits

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Installed on

opencode103

codex77

gemini-cli72

github-copilot70

amp70

kimi-cli66