Grilling — Agent Skill by Matt Pocock

From the author

Grill the user relentlessly about a plan, decision, or idea. Use when the user wants to stress-test their thinking, or uses any 'grill' trigger phrases.

— the description by Matt Pocock

AutoGineer summary

Written by AutoGineer from the skill’s own files, not by the author

The grilling skill transforms the agent into a relentless interviewer designed to stress-test plans, ideas, or decisions. It operates by constructing a design tree where every decision branches into subsequent dependencies. The agent manages this process in rounds, identifying the current frontier of questions that can be answered immediately. It provides recommended answers for each question, phrased so that a 'yes' confirms the recommendation, and it proactively delegates fact-finding tasks to sub-agents to minimize user burden. The process continues iteratively until the entire tree is explored and a shared understanding is reached.

What it does

Maps user ideas or plans into a structured design tree of decisions.
Identifies the current frontier of questions that are ready to be answered.
Provides recommended answers for each question to streamline the decision-making process.
Uses sub-agents to fetch necessary facts from the environment instead of asking the user.
Iteratively updates the tree based on user input to uncover new dependencies.
Ensures all branches are explored before confirming a shared understanding.

When to use it

When you need to stress-test a complex plan or decision.
When you want to identify hidden assumptions in your reasoning.
When you need a structured, step-by-step breakdown of a project's requirements.
When you want to ensure no aspect of a decision has been overlooked.

Advantages

Forces rigorous examination of every decision point.
Reduces user effort by providing recommended answers and automating fact-finding.
Prevents oversight by mapping out all downstream dependencies.
Maintains a clear, logical progression through complex topics.

Usage examples

“Grill me on my plan to migrate our database to a new cloud provider.”: The agent begins by mapping out the migration plan, asking the first round of questions regarding current infrastructure and constraints, providing recommendations for each.
“I have an idea for a new marketing campaign, grill me on it.”: The agent initiates a structured interview, breaking the campaign down into target audience, budget, and channel decisions, asking questions round-by-round.

Install

Download the skill as a ZIP:
https://mp-staging.autogineer.com/agent-skills/mattpocock/grilling/download
Unzip it into the cross-client skills folder of your project:
```
mkdir -p .agents/skills && unzip grilling.zip -d .agents/skills
```

Documentation by Matt Pocock

Interview the user relentlessly until you reach a shared understanding. Map this as a design tree: every decision branches into the decisions that hang off it.

Work the tree in rounds. The frontier is every decision whose prerequisites are already settled: the questions you can ask now without guessing at answers you haven't heard yet. Ask the whole frontier in one round: number each question and give your recommended answer. Then wait for the user's answers before the next round.

Format a round like so:

❓ **Q1** - **<question title>**: <question body, might be multiple paragraphs, including multiple choices>

➡️ <your recommended answer>

---

❓ **Q2** - **<question title>**: <question body, might be multiple paragraphs, including multiple choices>

➡️ <your recommended answer>

Word each question so "yes" accepts your recommended answer.

Each round the user answers reshapes the tree: settled decisions push the frontier outward and unblock questions that depended on them. Recompute the frontier and ask the next round. A question whose answer depends on another question still open in this round belongs to a later round, not this one.

Finding facts is your job, never the user's. When a frontier question needs a fact from the environment (filesystem, tools, etc.), dispatch a sub-agent with a fresh context window to find it; don't ask the user for anything you could look up yourself. Don't block on it: a running exploration is an unsettled prerequisite, so only the questions downstream of it wait for the sub-agent to report; ask the rest of the frontier now. The decisions are the user's: put each to them and wait.

The session is done when the frontier is empty: every branch of the design tree visited, nothing left silently assumed. Do not act on it until the user confirms you have reached a shared understanding.

Files

ATTRIBUTION.mdAdded by AutoGineer858 B
LICENSELicence file added by AutoGineer1.0 KiB
SKILL.md2.0 KiB
agents/openai.yaml113 B

ATTRIBUTION.md

Attribution

This folder is an unmodified copy of the Agent Skill "grilling", distributed by AutoGineer (https://autogineer.com/agent-skills).

Source: https://github.com/mattpocock/skills/tree/4ae2317ddb22b046e26455e4f9c9b3aaaf62212d/skills/productivity/grilling
Commit: 4ae2317ddb22b046e26455e4f9c9b3aaaf62212d
Created by: Matt Pocock (https://github.com/mattpocock)
Publisher: Matt Pocock (https://github.com/mattpocock)
Licence: MIT License (https://github.com/mattpocock/skills/blob/4ae2317ddb22b046e26455e4f9c9b3aaaf62212d/LICENSE)
Licence evidence: repository licence LICENSE
Retrieved: 2026-11-07

The skill's own files are unmodified copies. AutoGineer is not affiliated with or endorsed by the author or the publisher.

Files added by AutoGineer

ATTRIBUTION.md: this file, written by AutoGineer
LICENSE: copied from LICENSE

Requirements and compatibility

Works with: Claude Code, Claude apps, OpenAI Codex, GitHub Copilot, Cursor, Gemini CLI, Kiro, OpenCode, Goose, Amp, Roo Code, JetBrains Junie, Factory Droid, Devin (ex-Windsurf), Mistral Vibe, OpenHands, Letta

“Works with” means the tool reads the open Agent Skills format; a skill written for one tool may use features others lack.

Security

No issues found by our static scan· No issues found

A static scan is not a guarantee. Skills are third-party content: review a skill before you let an agent use it.

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