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addyosmani/planning-and-task-breakdown

addyosmani

planning-and-task-breakdown

Breaks work into ordered tasks. Use when you have a spec or clear requirements and need to break work into implementable tasks. Use when a task feels too large to start, when you need to estimate scope, or when parallel work is possible.

NewUpdated Sep 9, 2026

Planning and Task Breakdown

Overview

Decompose work into small, verifiable tasks with explicit acceptance criteria. Good task breakdown is the difference between an agent that completes work reliably and one that produces a tangled mess. Every task should be small enough to implement, test, and verify in a single focused session.

When to Use

  • You have a spec and need to break it into implementable units
  • A task feels too large or vague to start
  • Work needs to be parallelized across multiple agents or sessions
  • You need to communicate scope to a human
  • The implementation order isn't obvious

When NOT to use: Single-file changes with obvious scope, or when the spec already contains well-defined tasks.

The Planning Process

Step 1: Enter Plan Mode

Before writing any code, operate in read-only mode:

  • Read the spec and relevant codebase sections
  • Identify existing patterns and conventions
  • Map dependencies between components
  • Note risks and unknowns

Do NOT write code during planning. The output is a plan document saved to tasks/plan.md and a task list recorded in the task list target (see Output Files; default tasks/todo.md), not implementation.

Step 2: Identify the Dependency Graph

Map what depends on what:

Database schema
    │
    ├── API models/types
    │       │
    │       ├── API endpoints
    │       │       │
    │       │       └── Frontend API client
    │       │               │
    │       │               └── UI components
    │       │
    │       └── Validation logic
    │
    └── Seed data / migrations

Implementation order follows the dependency graph bottom-up: build foundations first.

Step 3: Slice Vertically

Instead of building all the database, then all the API, then all the UI — build one complete feature path at a time:

Bad (horizontal slicing):

Task 1: Build entire database schema
Task 2: Build all API endpoints
Task 3: Build all UI components
Task 4: Connect everything

Good (vertical slicing):

Task 1: User can create an account (schema + API + UI for registration)
Task 2: User can log in (auth schema + API + UI for login)
Task 3: User can create a task (task schema + API + UI for creation)
Task 4: User can view task list (query + API + UI for list view)

Each vertical slice delivers working, testable functionality.

Step 4: Write Tasks

Each task follows this structure, whether it lands in the markdown task list or as an item in an external tracker (see Output Files):

## Task [N]: [Short descriptive title]

**Description:** One paragraph explaining what this task accomplishes.

**Acceptance criteria:**
- [ ] [Specific, testable condition]
- [ ] [Specific, testable condition]

**Verification:**
- [ ] Tests pass: [the repository's focused-test command]
- [ ] Build succeeds: [the repository's build command]
- [ ] Manual check: [description of what to verify]

**Dependencies:** [Task numbers this depends on, or "None"]

**Files likely touched:**
- `src/path/to/file.ts`
- `tests/path/to/test.ts`

**Estimated scope:** [Small: 1-2 files | Medium: 3-5 files | Large: 5+ files]

Step 5: Order and Checkpoint

Arrange tasks so that:

  1. Dependencies are satisfied (build foundation first)
  2. Each task leaves the system in a working state
  3. Verification checkpoints occur after every 2-3 tasks
  4. High-risk tasks are early (fail fast)

Add explicit checkpoints to the task list target:

## Checkpoint: After Tasks 1-3
- [ ] All tests pass
- [ ] Application builds without errors
- [ ] Core user flow works end-to-end
- [ ] Review with human before proceeding

Task Sizing Guidelines

Size Files Scope Example
XS 1 Single function or config change Add a validation rule
S 1-2 One component or endpoint Add a new API endpoint
M 3-5 One feature slice User registration flow
L 5-8 Multi-component feature Search with filtering and pagination
XL 8+ Too large — break it down further

If a task is L or larger, it should be broken into smaller tasks. An agent performs best on S and M tasks.

When to break a task down further:

  • It would take more than one focused session (roughly 2+ hours of agent work)
  • You cannot describe the acceptance criteria in 3 or fewer bullet points
  • It touches two or more independent subsystems (e.g., auth and billing)
  • You find yourself writing "and" in the task title (a sign it is two tasks)

Output Files

  • Plan document: Save the implementation plan to tasks/plan.md. This is always a markdown file — design decisions, risks, and open questions don't map cleanly onto individual tracker issues.
  • Task list: Record each task in the task list target (defined below).

Create the tasks/ directory if it does not exist.

Never overwrite an incomplete plan. Before writing tasks/plan.md or tasks/todo.md, check whether they already exist and still contain unchecked tasks:

  • Same work being replanned (the user asked to revise or extend this plan) → update the existing files in place.
  • Different work → stop and ask. The unchecked tasks may be mid-build in another session. Do not delete, overwrite, or rename the existing files on your own; present the conflict and let the user decide (finish the old plan first, explicitly discard it, or tell you where the new plan should go).

The same rule applies to an external task list target: never bulk-close or delete another plan's open tracker items to make room for new ones.

Task List Target

The task list target is where tasks and checkpoints are recorded. It is defined once, here; every other reference in this skill defers to it.

  • Default: a checklist-style markdown file at tasks/todo.md. This is the convention the /build command and other downstream tooling expect. Use it unless the project says otherwise.
  • External tracker: if the project's agent rules (CLAUDE.md, AGENTS.md, etc.) or the user designate an issue tracker (e.g. GitHub Issues, Jira, Linear, bd/beads), create one tracker item per task instead of writing tasks/todo.md. Map the Step 4 structure onto the tracker's fields: acceptance criteria and verification steps in the item body, dependencies via the tracker's linking mechanism (bd dep add, "blocked by", etc.). Record Step 5 checkpoints as tracker items too, or as a checklist in the plan document if the tracker has no natural equivalent.

When using an external tracker, note it in tasks/plan.md (e.g. "Tasks tracked in Linear project FOO") so downstream steps and future sessions know where to look, and keep the plan document's Task List section as an ordered index of tracker item IDs or links rather than a duplicate checklist.

Plan Document Template

# Implementation Plan: [Feature/Project Name]

## Overview
[One paragraph summary of what we're building]

## Architecture Decisions
- [Key decision 1 and rationale]
- [Key decision 2 and rationale]

## Task List

### Phase 1: Foundation
- [ ] Task 1: ...
- [ ] Task 2: ...

### Checkpoint: Foundation
- [ ] Tests pass, builds clean

### Phase 2: Core Features
- [ ] Task 3: ...
- [ ] Task 4: ...

### Checkpoint: Core Features
- [ ] End-to-end flow works

### Phase 3: Polish
- [ ] Task 5: ...
- [ ] Task 6: ...

### Checkpoint: Complete
- [ ] All acceptance criteria met
- [ ] Ready for review

## Risks and Mitigations
| Risk | Impact | Mitigation |
|------|--------|------------|
| [Risk] | [High/Med/Low] | [Strategy] |

## Open Questions
- [Question needing human input]

When tasks live in an external tracker, keep the Task List section above as an ordered index of tracker item IDs or links instead of a duplicate checklist.

Parallelization Opportunities

When multiple agents or sessions are available:

  • Safe to parallelize: Independent feature slices, tests for already-implemented features, documentation
  • Must be sequential: Database migrations, shared state changes, dependency chains
  • Needs coordination: Features that share an API contract (define the contract first, then parallelize)

Common Rationalizations

Rationalization Reality
"I'll figure it out as I go" That's how you end up with a tangled mess and rework. 10 minutes of planning saves hours.
"The tasks are obvious" Write them down anyway. Explicit tasks surface hidden dependencies and forgotten edge cases.
"Planning is overhead" Planning is the task. Implementation without a plan is just typing.
"I can hold it all in my head" Context windows are finite. Written plans survive session boundaries and compaction.
"The old tasks/plan.md is stale, I'll just replace it" Unchecked tasks may be mid-build in another session. Overwriting them destroys work state that exists nowhere else. Stop and ask.

Red Flags

  • Starting implementation without a written task list
  • Overwriting a tasks/plan.md or tasks/todo.md that still has unchecked tasks for different work, without asking
  • Writing tasks/todo.md when the project has designated an external tracker (or scattering tasks across both)
  • Tasks that say "implement the feature" without acceptance criteria
  • No verification steps in the plan
  • All tasks are XL-sized
  • No checkpoints between tasks
  • Dependency order isn't considered

Verification

Before starting implementation, confirm:

  • Every task has acceptance criteria
  • Every task has a verification step
  • Task dependencies are identified and ordered correctly
  • Tasks are recorded in the task list target (default tasks/todo.md)
  • No pre-existing incomplete plan was overwritten without explicit user confirmation
  • No task touches more than ~5 files
  • Checkpoints exist between major phases
  • The human has reviewed and approved the plan

See Also

Acceptance criteria are per-task and answer "did we build the right thing?". They sit on top of the project-wide Definition of Done, the standing bar every task clears before it counts as done. See ../../references/definition-of-done.md.

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Overall Score

89/100

Grade

A

Excellent

Grades are signals, not a certification. Always review a skill yourself before use.

Safety

92

Quality

88

Clarity

90

Completeness

85

Summary

This skill teaches agents how to decompose work into small, verifiable tasks with explicit dependencies, acceptance criteria, and verification steps. It guides users through a five-step planning process: read-only analysis, dependency mapping, vertical slicing, task structuring, and checkpoint ordering. Output is a plan document and task list (default `tasks/todo.md` or external tracker) that enables parallelization, scope estimation, and reliable implementation tracking.

Detected Capabilities

file read (spec and codebase)plan document creation (markdown write to tasks/plan.md)task list creation (markdown write to tasks/todo.md or external tracker)dependency analysis

Trigger Keywords

Phrases that agents use to match this skill to user intent.

break down large featureestimate project scopetask planning from specidentify dependenciesparallelize workstructured task listverify implementation plan

Use Cases

  • Breaking a large feature specification into implementable tasks
  • Estimating project scope and work distribution across multiple agents or sessions
  • Identifying dependencies between components before implementation begins
  • Establishing a work plan with clear acceptance criteria and verification checkpoints
  • Parallelizing independent feature slices across concurrent work streams
  • Communicating scope and progress to humans through a structured task list

Quality Notes

  • Excellent structure with clear section hierarchy and logical progression through the planning workflow
  • Comprehensive examples illustrate the difference between poor (horizontal) and good (vertical) task slicing, making the core concept concrete
  • Task sizing guidelines table provides concrete reference points (XS through XL with file counts and scope definitions)
  • Strong emphasis on safety: explicit instruction not to overwrite incomplete plans without user confirmation, protecting work state across sessions
  • Verification checklist at the end provides a concrete sign-off gate before implementation begins
  • Red flags section surfaces common mistakes agents and users make (starting without a plan, overwriting stale tasks, scattering across trackers)
  • Handles both default (tasks/todo.md) and external tracker targets, with clear guidance on when to use each
  • Parallelization section explicitly identifies what can and cannot be parallelized, reducing coordination friction
  • Common rationalizations table directly addresses cognitive biases that lead to skipped planning
  • Open questions and risks sections in template encourage explicit capture of unknowns before implementation
  • Dependency graph example is visual and immediately understandable
  • Step 4 task template is comprehensive but concise — files touched, scope, dependencies, verification all included
Model: claude-haiku-4-5-20251001Analyzed: Sep 9, 2026

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Version History

  1. v1.2

    Content updated

    ✦ AIAdds formal Output Files section requiring tasks to be recorded in task list target (default `tasks/todo.md`, or external tracker) and prohibits overwriting incomplete plans.

    2026-09-09

    LATEST
  2. v1.1

    Content updated

    ✦ AIAdds reference to Definition of Done criteria in See Also section.

    2026-06-28

    View This Version
  3. v1.0

    2026-05-02

    View This VersionInitial version

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