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Grilling Plan Stress-Tester

Interviews you in rounds about a plan or idea until every branch of the decision tree is settled

Source Download skill
Repository
mattpocock/skills
Stars
309,658
Licence
MIT
Files
2 files

What it does

Once installed, when you ask the agent to stress-test a plan, decision, or idea, it stops giving quick feedback and instead interviews you. It maps your decisions as a tree, asks the currently answerable questions in numbered batches, and gives a recommended answer to each, then waits for your replies before going deeper. It keeps going until no open questions remain, and it won't act on the plan until you confirm you've reached a shared understanding.

Great for

  • People who want their thinking challenged before committing to a project, product, or major decision
  • Developers planning a feature or architecture who want every assumption surfaced
  • Anyone who tends to skip over edge cases and wants a structured, persistent questioning process

Skip it if

  • Quick answers or simple tasks, since the process is deliberately slow and repetitive (it asks many questions before doing anything)
  • Situations where you want the agent to just make decisions and proceed, because the skill insists decisions belong to you
  • Users who find being questioned repeatedly frustrating or who need a short response

Try asking

  • “Grill me about my plan to launch a paid newsletter before I commit any money”
  • “Stress-test my idea for a mobile app that tracks habits; ask one round of questions at a time”
  • “I want to be grilled on the architecture decision between a monolith and microservices”
Step-by-step guide: how to use Grilling Plan Stress-TesterInstall, first run, examples, tips and FAQs

Install in 3 steps

  1. 1

    Download the skill

    The ZIP contains the 2 original files, the MIT licence and an attribution note.

    grilling.zip
  2. 2

    Add it to your agent

    Claude Code (all projects)

    mkdir -p ~/.claude/skills && unzip grilling.zip -d ~/.claude/skills/

    Claude Code / Agent SDK (this project only)

    mkdir -p .claude/skills && unzip grilling.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

  • Give the agent a short description of your plan up front so the first round of questions has context
  • Answer each numbered question directly; the agent recomputes the tree from your answers, so vague replies slow things down
  • Say when you feel the shared understanding is complete, since the agent will not act until you confirm

What's inside

  • agents/openai.yaml
  • SKILL.md

Redistributed unmodified from mattpocock/skills 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.