Skill · Think
Devil's advocate
Have an AI argue hard against your plan, belief or decision, so you hear the strongest objections before reality delivers them.
The skill#
Act as a sharp, fair devil's advocate.
My idea or decision: [DESCRIBE YOUR IDEA OR DECISION]
Why I believe it: [YOUR REASONS]
1. Argue the strongest possible case against it, as a smart critic would.
2. Attack my reasons one by one: which are weak, unproven or wishful?
3. Point out what I may be ignoring because I want this to be true.
4. Describe one realistic scenario in which this goes badly.
5. Say what evidence would change your mind, and what would change mine.
Do not soften the criticism, and do not invent facts about my situation. End with the one question I most need to answer honestly.How to use it#
- Copy the skill and describe your idea and why you believe in it.
- Read the objections without arguing back; note the ones that sting.
- Answer the final question honestly, or test it, before you commit.
Example#
Describe a plan to quit your job and launch a newsletter. You get the case against it: thin evidence of demand, an optimistic revenue assumption, and a realistic failure scenario, ending with "How many paying readers do you have today?"
Quick and strict versions#
Use the quick version for everyday checks and the strict version when the result matters.
Give me the three strongest objections to this idea, as a smart critic would put them. Be direct.
Idea: [DESCRIBE YOUR IDEA]Act as a red team assigned to find why this will fail.
Plan: [DESCRIBE YOUR PLAN]
Goal: [WHAT SUCCESS LOOKS LIKE]
Constraints: [BUDGET, TIME, PEOPLE]
1. List every assumption the plan depends on and rate how likely each is to be false.
2. For the three riskiest assumptions, describe how they break and what happens next.
3. Identify the cheapest test that would prove or disprove each one.
4. Name competitors, incentives or people who might work against it.
5. Argue for the best alternative plan.
Be specific, not generic. Return: Assumption table | Failure stories | Tests | Best alternativeUse it as an agent skill#
Save this as SKILL.md in a folder named after the skill, and agents that support skills (Claude, Claude Code and other skill-aware agents) can load it automatically when the task fits.
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name: devils-advocate
description: Use when the user wants their idea, plan, belief or decision challenged, stress-tested or argued against.
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# Devil's advocate
Fill each [BRACKETED] field from the conversation. If one is missing, ask the user for it before starting.
Act as a sharp, fair devil's advocate.
My idea or decision: [DESCRIBE YOUR IDEA OR DECISION]
Why I believe it: [YOUR REASONS]
1. Argue the strongest possible case against it, as a smart critic would.
2. Attack my reasons one by one: which are weak, unproven or wishful?
3. Point out what I may be ignoring because I want this to be true.
4. Describe one realistic scenario in which this goes badly.
5. Say what evidence would change your mind, and what would change mine.
Do not soften the criticism, and do not invent facts about my situation. End with the one question I most need to answer honestly.
Frequently asked questions
Won't the AI just agree with me?
AI models tend to be agreeable. This skill explicitly assigns it the critic's role and asks it not to soften, which works well in practice.
Is this the same as a pre-mortem?
Close. Devil's advocate argues against the idea itself; a pre-mortem assumes it already failed and works out why.
What should I do with the objections?
Pick the one or two that would sink the plan if true, and find a cheap way to test them.