grill-me

Interrogate plans and designs to expose weak assumptions and unclear decisions.

345|9|Updated Jun 19, 2026
One-click install
npx skills add https://github.com/dmmulroy/skills --skill grill-me-dmmulroy
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: grill-me
Source: https://github.com/dmmulroy/skills/tree/main/grill-me
Command: npx skills add https://github.com/dmmulroy/skills --skill grill-me-dmmulroy

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This Skill helps you pressure-test a plan or design before you commit to it, exposing weak assumptions, missing details, and unclear decisions early.

Core Features & Use Cases

  • Relentless Interviewing: Pushes a proposal with sharp follow-up questions until the reasoning is specific and defensible.
  • Plan Clarification: Surfaces gaps in scope, sequencing, dependencies, and tradeoffs for work like product ideas, technical designs, and implementation plans.
  • Use Case: When you have a draft architecture or roadmap and want to find the hidden risks before sharing it with a team, this Skill helps tighten it up.

Quick Start

Use the grill-me skill to challenge my current plan until the assumptions, risks, and next steps are clear.

Frequently Asked Questions about grill-me

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

FAQPage Schema
How do I pressure-test a technical design to expose weak assumptions before implementation?

To pressure-test a technical design, you interrogate the plan through a relentless question loop until reasoning is specific, exposing weak assumptions, missing details, and unclear decisions before execution.

What is the best way to find hidden risks in a draft architecture or product roadmap?

Finding hidden risks in a draft architecture involves applying sharp follow-up questions to surface gaps in scope, sequencing, dependencies, and tradeoffs, ensuring the roadmap is defensible before team presentation.

Can I use relentless questioning to clarify scope and dependencies for a software refactor plan?

Yes, you can use relentless questioning to clarify scope and dependencies for a software refactor plan by pushing the proposal with evidence-backed clarification until all risks and next actions are explicitly resolved.

How do I validate implementation proposals through a design critique interview?

Validating implementation proposals through a design critique interview requires demanding evidence-backed clarification for each decision, pushing the proposal until vague reasoning becomes specific and defensible.

When do I need to use a questioning loop to review an architecture plan?

You need a questioning loop to review an architecture plan when you have a draft design requiring pressure-testing to tighten it up, ensuring hidden risks are found and assumptions are clear before committing to execution.