Overview

The Planning skill helps you create structured, phased plans for work that spans 5+ items. It guides you through decomposition, checkpoint placement, dependency mapping, agent assignment, and orchestration design.

Invoke with /plan.

Step 1: Understand the Scope

Before decomposing, understand what you're building:

1. •Read the requirements - Gather all input: user request, linked issues, design docs, existing code
2. •Identify the category type - Is this a PROJ (new feature), BUG (fix), or IMP (improvement)?
3. •Estimate total effort - Rough hours for the entire body of work
4. •Identify boundaries - What's in scope vs out of scope?

Scope Signals

If total effort is under ~4h (2-3 items), a flat list of ITEMs with dependencies is sufficient — skip checkpoints.

Step 2: Decompose into Items

Break the work into atomic ITEMs following the Task Granularity Guidelines:

• •Each ITEM takes 1-2 hours
• •Each ITEM has self-contained testing
• •Each ITEM is assigned to exactly one agent
• •Each ITEM touches at most 3-4 files

Decomposition Strategies

• •Bottom-up: Start from the lowest dependency (data model, types) and build upward
• •Top-down: Start from the user-facing outcome and work backward to what's needed
• •Vertical slices: Each item delivers a thin, testable slice through the stack

Naming Convention

Use descriptive titles that make the work clear at a glance:

** ITEM Define search index data types            ;; Good: specific
** ITEM Set up search                              ;; Bad: too vague
** ITEM Implement search index, query API, and UI  ;; Bad: too large

Step 3: Identify Phases

Group items into phases by finding natural boundaries. Look for these patterns:

Phase Boundary Signals

Phase Sizing

• •2-5 ITEMs per phase is the sweet spot
• •Fewer than 2 ITEMs doesn't justify a checkpoint
• •More than 5 ITEMs suggests a missing intermediate boundary

Typical Phase Patterns

Backend → Frontend

Phase 1: Data types, Rust modules, Tauri commands
Phase 2: Svelte components, stores, UI integration
Phase 3: E2E tests, polish, edge cases

Infrastructure → Features → Polish

Phase 1: Scaffolding, configuration, base types
Phase 2: Core feature implementation
Phase 3: Error handling, performance, documentation

Step 4: Create Checkpoints

Place a ** CHECKPOINT heading between each phase group. Each checkpoint defines what must be true before proceeding.

Checkpoint Heading Format

** CHECKPOINT Descriptive phase boundary name
:PROPERTIES:
:CUSTOM_ID: CHK-NNN-MM-slug
:CRITERIA: Single sentence defining done for this phase
:VERIFY: Shell command(s) that confirm the checkpoint
:REVIEW_BY: agent-name(s) who should review
:END:

*** Gate Conditions
- [ ] Specific verifiable condition 1
- [ ] Specific verifiable condition 2
- [ ] Specific verifiable condition 3

Property Reference

Naming Convention

CHK-NNN-MM-slug where:

• •NNN is the parent category number (e.g. 007 for PROJ-007)
• •MM is the sequential checkpoint number within that category (01, 02, …)
• •slug is a short kebab-case description

Writing Good Gate Conditions

Gate conditions should be:

• •Verifiable — can be checked by running a command or inspecting output
• •Specific — "cargo test passes for search module" not "tests pass"
• •Complete — cover the meaningful outputs of the phase, not just compilation

;; Good gate conditions:
- [ ] cargo test passes for search module
- [ ] Tauri command returns results for test corpus
- [ ] No clippy warnings in new code

;; Bad gate conditions:
- [ ] Code looks good
- [ ] Everything works
- [ ] Tests pass

Step 5: Map Dependencies

Wire DEPENDS properties between ITEMs to encode execution order.

Rules

1. •ITEM-to-ITEM only — Dependencies point to ITEM IDs, never to CHK-* IDs
2. •Items after a checkpoint depend on items before it — The last item(s) of phase N should be in the DEPENDS of the first item(s) of phase N+1
3. •Minimize transitive dependencies — If A→B→C, item C only needs DEPENDS: B (not both A and B)
4. •Cross-category dependencies use the PROJ-NNN:ITEM-XXX syntax

Dependency Diagram

For a 2-phase project:

Phase 1:  ITEM-070 ──→ ITEM-071
                              │
          ── CHECKPOINT ──────┤
                              │
Phase 2:  ITEM-072 (DEPENDS: ITEM-071) ──→ ITEM-073

Step 6: Assign Agents

Match each ITEM to the agent best suited for the work. Consult the Agent Registry for available agents and their expertise.

Assignment Guidelines

Checkpoint Handoffs

Note where agent responsibility changes at checkpoint boundaries. This is a natural review point:

• •The outgoing agent's work should be reviewed at the checkpoint
• •The incoming agent reads the checkpoint's gate conditions to understand the starting state

Step 7: Design Orchestration

Define how the plan will be executed, including parallelization and coordination.

Parallelization Strategy

Identify which items can run concurrently:

Sequential (dependency chain):
  ITEM-070 → ITEM-071 → [CHECKPOINT] → ITEM-072

Parallel (independent within phase):
  ITEM-073 ─┐
  ITEM-074 ─┤→ [CHECKPOINT]
  ITEM-075 ─┘

Agent Coordination

For each phase, specify:

1. •Which agents are active
2. •What they're working on in parallel
3. •What synchronization points exist (checkpoints)

Testing at Each Checkpoint

Define the test strategy per phase:

Step 8: Write the Plan File

Assemble the org file in the appropriate directory:

• •Projects: @tasks/projects/PROJ-NNN-name.org
• •Bugfixes: @tasks/bugfixes/BUG-NNN-name.org
• •Improvements: @tasks/improvements/IMP-NNN-name.org

File Structure

#+TITLE: Short Project Title
#+STARTUP: overview

* PROJ-NNN Project Title
:PROPERTIES:
:CUSTOM_ID: PROJ-NNN
:GOAL: Clear outcome statement
:END:

;; Phase 1 items
** ITEM First task
:PROPERTIES:
...
:END:

** ITEM Second task
:PROPERTIES:
...
:END:

** CHECKPOINT Phase 1 complete
:PROPERTIES:
...
:END:

;; Phase 2 items
** ITEM Third task
:PROPERTIES:
...
:END:

** CHECKPOINT Phase 2 complete
:PROPERTIES:
...
:END:

Step 9: Validate

Run validation to confirm the plan file is well-formed:

emacsclient -s sakya -e '(prd-validate-all-cli)'

What to Check

1. •No validation errors — All ITEMs have required properties
2. •No broken dependencies — All DEPENDS targets exist
3. •No circular dependencies — Dependency graph is a DAG
4. •Checkpoints ignored — CHECKPOINT headings produce no errors (they're a convention, not validated entities)

If validation fails, fix the reported issues and re-validate.

Checkpoint Reference

What is a Checkpoint?

A checkpoint is a ** CHECKPOINT heading placed between groups of ITEMs in a category file. It marks a phase boundary with explicit criteria that must be satisfied before proceeding to the next phase.

Checkpoints are a convention, not a validated entity type. The elisp validator silently ignores them because CHECKPOINT is not a TODO keyword and CHK-* IDs don't match the category ID pattern. This means:

• •No elisp changes required
• •No impact on metrics, dashboard, velocity, or burndown
• •They serve as human-readable (and agent-readable) planning structure

Full Property Specification

Important Constraints

• •ITEMs should NOT use DEPENDS to reference CHK-* IDs — dependencies point to ITEMs only
• •Checkpoints don't have a TODO state — they're structural markers, not tasks
• •Gate condition checklists use standard org-mode - [ ] syntax

Worked Example

A project with 2 phases and checkpoints:

* PROJ-007 Search Feature
:PROPERTIES:
:CUSTOM_ID: PROJ-007
:GOAL: Full-text search across manuscripts
:END:

** ITEM Create search index module
:PROPERTIES:
:CUSTOM_ID: ITEM-070-search-index
:AGENT: [[file:agents/rust-architect.org::#core][rust-architect:core]]
:EFFORT: 2h
:PRIORITY: #A
:TEST_PLAN: compile, test-rust
:END:

*** Description
Implement a search index using tantivy. Define the schema, indexing pipeline,
and query interface as a Rust module.

*** Acceptance Criteria
- [ ] Search index builds from document corpus
- [ ] Query returns ranked results
- [ ] Module has unit tests

** ITEM Add indexing Tauri command
:PROPERTIES:
:CUSTOM_ID: ITEM-071-index-command
:AGENT: [[file:agents/rust-architect.org::#core][rust-architect:core]]
:EFFORT: 1h
:PRIORITY: #A
:DEPENDS: ITEM-070-search-index
:TEST_PLAN: compile, test-rust
:END:

*** Description
Expose the search index as Tauri commands: index_documents and search_query.

*** Acceptance Criteria
- [ ] Tauri command indexes documents
- [ ] Tauri command returns search results as JSON
- [ ] Integration test exercises the IPC boundary

** CHECKPOINT Backend search ready
:PROPERTIES:
:CUSTOM_ID: CHK-007-01-backend-ready
:CRITERIA: Search index builds and queries return results via Tauri command
:VERIFY: cargo test --lib search
:REVIEW_BY: rust-architect
:END:

*** Gate Conditions
- [ ] cargo test passes for search module
- [ ] Tauri command returns results for test corpus
- [ ] No clippy warnings

** ITEM Create search UI component
:PROPERTIES:
:CUSTOM_ID: ITEM-072-search-ui
:AGENT: [[file:agents/svelte-developer.org::#core][svelte-developer:core]]
:EFFORT: 2h
:PRIORITY: #A
:DEPENDS: ITEM-071-index-command
:TEST_PLAN: compile, test-svelte, e2e
:END:

*** Description
Build the search interface: input field, results list, and navigation to
matching documents. Calls the search_query Tauri command.

*** Acceptance Criteria
- [ ] Search input triggers query on keypress (debounced)
- [ ] Results display with title and context snippet
- [ ] Clicking a result navigates to the document

** CHECKPOINT Search feature complete
:PROPERTIES:
:CUSTOM_ID: CHK-007-02-feature-complete
:CRITERIA: User can search manuscripts and navigate to results
:VERIFY: bun run test:e2e -- --grep search
:REVIEW_BY: svelte-developer, testing-engineer
:END:

*** Gate Conditions
- [ ] E2E test covers search flow
- [ ] Visual regression passes
- [ ] Performance: <200ms for 1000-document corpus

See Also

• •Process Registry
• •Task Runner - For picking and starting individual tasks
• •Multi-File Changes - For complex cross-file work
• •Agent Registry - Available agents and expertise
• •Reference Guide - Full PRD system documentation
• •Task Granularity Guidelines - Sizing individual ITEMs