Agent skill

Milestone Planning

by tmdgusya in tmdgusya/engineering-discipline

Decomposes complex, multi-day tasks into optimized milestones (ultraplan).

No licenceAuto-check passedProduct & Project Management

Install Milestone Planning

skills CLI
$ npx skills add tmdgusya/engineering-discipline --skill milestone-planning -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install tmdgusya/engineering-discipline milestone-planning --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/tmdgusya/engineering-discipline.git skills-src && mkdir -p .claude/skills && cp -r skills-src/skills/milestone-planning .claude/skills/milestone-planning && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
milestone-planning
GitHub stars
125
Token cost
~5.5k tokens
SKILL.md length
2,149 words
Files
1
Skills in repo
11
Repo updated
First seen
Licence
None found

At a glance

Decomposes complex, multi-day tasks into optimized milestones (ultraplan).

  • Works in 8 steps: Problem Framing + Broad Exploration → Draft Decomposition (two skeletons, then… → Adversarial Critic Panel → …
  • The user says plan milestones
  • SKILL.md covers Core Principle, Hard Gates, When To Use and When NOT To Use, plus 5 more sections
  • Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md

What it does

Milestone Planning is an agent skill from tmdgusya/engineering-discipline. Decomposes complex, multi-day tasks into optimized milestones (ultraplan). Broad parallel exploration grounds a draft milestone DAG, then independent adversarial critics attack the draft in rounds until no blocking findings remain. Triggers when the user says "plan milestones", "break this into milestones", "ultraplan", or when long-run harness needs milestone generation.

Its SKILL.md is about 5.5k tokens, which your agent loads only when the skill is triggered. It is a single SKILL.md file with no bundled scripts.

It sits in Product & Project Management, covering Project management. The repository describes itself as: SKILL for engineering-discipline.

When your agent uses it

  • The user says plan milestones
  • Break this into milestones
  • Long-run harness needs milestone generation

Example prompts

  • “plan milestones”
  • “break this into milestones”
  • “ultraplan”
  • “/milestone-planning”

Workflow steps

8 steps, taken from the step headings in SKILL.md.

  1. Problem Framing + Broad Exploration
  2. Draft Decomposition (two skeletons, then one draft)
  3. Adversarial Critic Panel
  4. Revision Loop (Critique Until Dry)
  5. 5: Integration Verification Milestone
  6. 6: Independent DAG Validation
  7. User Review and Lock
  8. Save Milestone Artifacts

What it can do on your machine

Read from SKILL.md and the folder at commit 137dead. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    No scripts in the folder and no shell commands in SKILL.md (its code samples are markdown).

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Milestone Planning loads about 5.5k tokens when it runs. Until then it costs about 98 tokens; SKILL.md has 2,149 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~98
When it runs · the whole SKILL.md, loaded when a task matches
~5.5k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

Without a licence we can't republish the file, so here is its outline and opening line. It has 2,149 words (~5,501 tokens).

“Decomposes a complex task into milestones in three moves: explore the codebase broadly in parallel, draft a milestone DAG grounded in what exploration found, then submit the draft to a panel of adversarial critics who attack it in rounds until…”

— opening of SKILL.md by tmdgusya
name
milestone-planning

Read the full SKILL.md on GitHub

Files

Just SKILL.md in skills/milestone-planning of tmdgusya/engineering-discipline.

Open the folder on GitHubat commit 137dead

Compare with similar skills

Milestone Planning next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

Milestone Planning compared with similar skills
SkillStarsUsed inTokensAuto-checkLicenceRepo updated
Milestone Planning this skilltmdgusya/engineering-discipline125—~5.5kAutomated safety check: PassNone
CCPM Project Managementautomazeio/ccpm8.4k—~1.1kAutomated safety check: PassMIT
Uvastral-sh/claude-code-plugins3132 repos~980Automated safety check: PassApache-2.0
Project Managementkunchenguid/firstmate7.8k—~2.1kAutomated safety check: PassMIT
Hivemind Goalsactiveloopai/hivemind1.6k—~1.7kAutomated safety check: NotesApache-2.0
Ichartjswanghetommy/ichartjs352—~4.3kAutomated safety check: PassApache-2.0

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  • Plan Crafting

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  • Review Work

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    Use after run-plan completes to independently verify the implementation.

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  • Run Plan

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Questions about Milestone Planning

What does Milestone Planning do?

Decomposes complex, multi-day tasks into optimized milestones (ultraplan). Milestone Planning is an agent skill from tmdgusya/engineering-discipline. Decomposes complex, multi-day tasks into optimized milestones (ultraplan).

When should I use Milestone Planning?

Milestone Planning fits situations like: the user says plan milestones; break this into milestones; long-run harness needs milestone generation.

How do I install Milestone Planning in Claude Code?

Run `npx skills add tmdgusya/engineering-discipline --skill milestone-planning -a claude-code`. Or copy the skill folder (skills/milestone-planning in tmdgusya/engineering-discipline) into .claude/skills/milestone-planning in your project. Claude Code loads it when a task matches its description.

How do I install Milestone Planning in Codex?

Run `npx skills add tmdgusya/engineering-discipline --skill milestone-planning -a codex`. Or copy the skill folder (skills/milestone-planning in tmdgusya/engineering-discipline) into .agents/skills/milestone-planning in your project. Codex loads it when a task matches its description.

Can I use Milestone Planning in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add tmdgusya/engineering-discipline --skill milestone-planning -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/milestone-planning, .gemini/skills/milestone-planning, .github/skills/milestone-planning and .opencode/skills/milestone-planning in your project.

What does Milestone Planning need to run?

SKILL.md names no scripts, command-line tools or credentials: Milestone Planning is instructions for the agent only.

Does Milestone Planning access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is Milestone Planning safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does Milestone Planning use?

No licence was found for Milestone Planning or its repository. Without one, default copyright applies: ask the author before reusing or redistributing it.

How many tokens does Milestone Planning use?

About 5.5k tokens (SKILL.md is roughly 22k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full.

What are the alternatives to Milestone Planning?

Skills that share tags, products or a category with Milestone Planning: CCPM Project Management (automazeio/ccpm, 8.4k stars), Uv (astral-sh/claude-code-plugins, 313 stars), Project Management (kunchenguid/firstmate, 7.8k stars) and Hivemind Goals (activeloopai/hivemind, 1.6k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Milestone Planning?

tmdgusya (a GitHub user) maintains it in tmdgusya/engineering-discipline, which has 125 GitHub stars. The repository holds 11 skills in this directory. The repository was last updated on July 3, 2026.

Source: tmdgusya/engineering-discipline on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.