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grill-me

Challenge plans and designs through rigorous questioning to expose assumptions and risks.

1|Updated Mar 19, 2026
Search Tags:#planning#interview#assumptions#design review#critique#grilling
One-click install
npx skills add https://github.com/ian-pascoe/dotfiles-chezmoi --skill grill-me-ian-pascoe
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: grill-me
Source: https://github.com/ian-pascoe/dotfiles-chezmoi/tree/main/dot_agents/skills/grill-me
Command: npx skills add https://github.com/ian-pascoe/dotfiles-chezmoi --skill grill-me-ian-pascoe

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

It helps you pressure-test a plan or design before you commit to it, so weak assumptions, missing details, and unclear tradeoffs surface early.

Core Features & Use Cases

  • Rigorous critique: Pushes on logic, edge cases, and blind spots with focused follow-up questions.
  • Plan refinement: Helps improve strategy docs, product ideas, system designs, and project proposals.
  • Use case: Use it when you want an honest, demanding review of a draft before sharing it with stakeholders or starting execution.

Quick Start

Ask this skill to run a grilling session on your plan or design and challenge it until the major weaknesses are exposed.

Frequently Asked Questions about grill-me

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I stress test a product strategy before sharing it with stakeholders?▼

To stress test a product strategy, run a probing interview flow that challenges your draft with rigorous questioning. This exposes assumptions, gaps, tradeoffs, and weak reasoning before stakeholder review.

What is a design critique interview and how does it expose assumptions?▼

A design critique interview is a probing flow applying rigorous questioning to a plan. It exposes hidden assumptions, missing details, and unclear tradeoffs by pushing on logic and edge cases.

Can I use a grilling session to review an architecture proposal?▼

Yes, you can use a grilling session to review an architecture proposal. It applies rigorous questioning to high-stakes system designs, challenging logic and blind spots until major weaknesses surface.

What's the best way to challenge a project plan for blind spots?▼

The best way to challenge a project plan for blind spots is through focused follow-up questions targeting logic and edge cases. This demanding review surfaces missing details before execution begins.

When should I avoid using a rigorous questioning critique on my drafts?▼

Avoid using a rigorous questioning critique when your draft is an unstructured idea. This process requires a baseline plan to effectively probe for tradeoffs, risks, and gaps.

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