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Planning with Files (Kiro)

Keeps persistent markdown plans on disk so an agent can track multi-step work across long sessions

Source Download skill
Repository
OthmanAdi/planning-with-files
Stars
27,822
Licence
MIT
Files
11 files

What it does

It teaches the agent to write its plan, findings and progress into markdown files in your project (under .kiro/plan/) instead of relying only on its chat memory. Each turn it re-reads the plan so it stays on track through long or multi-step tasks, and it can check that the plan's phase markers are formatted correctly. It also sets up a small steering file so the Kiro editor keeps those planning files in view.

Great for

  • Developers running long coding or research tasks with an AI agent that need 5 or more tool calls
  • People who lose track when an agent's chat context grows long or gets reset
  • Teams that want a visible, editable plan file in the repository for review

Skip it if

  • Quick one-off questions or small edits, where the planning overhead adds noise
  • Users outside the Kiro or SKILL.md ecosystem who expect the bootstrap scripts to work without a POSIX shell or PowerShell and Python 3 installed
  • Sensitive projects where the plan files might capture confidential details, since they are plain text written into the workspace and may be committed to version control

Try asking

  • “Plan the migration of this project from REST to GraphQL, and track each phase in the plan file”
  • “Research three competing database options and record findings as you go”
  • “Set up planning files for this workspace, then continue the refactor across several sessions”
  • “Check whether my task plan file is formatted correctly before we start the implementation”
Step-by-step guide: how to use Planning with Files (Kiro)Install, first run, examples, tips and FAQs

Install in 3 steps

  1. 1

    Download the skill

    The ZIP contains the 11 original files, the MIT licence and an attribution note.

    planning-with-files.zip
  2. 2

    Add it to your agent

    Claude Code (all projects)

    mkdir -p ~/.claude/skills && unzip planning-with-files.zip -d ~/.claude/skills/

    Claude Code / Agent SDK (this project only)

    mkdir -p .claude/skills && unzip planning-with-files.zip -d .claude/skills/

    Claude apps (web/desktop): Settings → Capabilities → Skills → Upload skill, and choose the ZIP.

  3. 3

    Ask for the task

    No special command needed — the agent reads the skill's description and loads it when your request matches. Try one of the prompts above.

Get better results

  • Run the bootstrap script once per workspace, then let the agent fill in the generated task_plan.md rather than replacing its phase format
  • Review the .kiro/plan/ files and decide whether to add them to .gitignore if they contain sensitive notes
  • Use the validation step after editing phase structure so the format check passes before substantive work

What's inside

  • assets/scripts/bootstrap.sh
  • assets/scripts/check-complete.sh
  • assets/scripts/session-catchup.py
  • assets/templates/findings.md
  • assets/templates/planning-context.md
  • assets/templates/progress.md
  • assets/templates/task_plan.md
  • references/manus-principles.md
  • references/planning-rules.md
  • references/planning-templates.md
  • SKILL.md

Redistributed unmodified from OthmanAdi/planning-with-files under the MIT licence. The assessment was drafted with AI from the skill's files on 2026-10-29. Skills can instruct your agent to run code — read SKILL.md and any scripts before installing.