explaingit

orange2ai/devils-advocate-skill

25Audience · generalComplexity · 1/5ActiveLicenseSetup · easy

TLDR

Markdown skill file that flips an AI assistant into a harsh critic so it pokes holes in ideas instead of agreeing with everything.

Mindmap

mindmap
  root((Devils Advocate))
    Inputs
      User idea
      Trigger phrase
      Project context
    Outputs
      Cold critique
      Socratic questions
      Failure mode list
      Exit signal
    Use Cases
      Pre code review
      Technical design review
      Product critique
      Investor pitch practice
      Personal decisions
    Tech Stack
      Markdown
      ColaOS
      System prompt

Things people build with this

USE CASE 1

Stress-test product requirements before any code gets written

USE CASE 2

Run a hostile technical design review against an architecture proposal

USE CASE 3

Practice an investor pitch against a model playing a skeptical VC

USE CASE 4

Get a brutally honest critique of a personal decision instead of agreement

Tech stack

MarkdownColaOS

Getting it running

Difficulty · easy Time to first run · 5min

Paste the SKILL.md contents into any agent's system prompt, or copy the folder into ~/.cola/skills/ for ColaOS.

MIT permits commercial use, modification, and distribution as long as the original copyright notice is kept.

In plain English

Devil's Advocate is a tiny "skill" file for AI agent systems, written in Chinese. A skill in this context is a markdown file that gets injected into an AI assistant's system prompt to change how it behaves. This particular skill is designed for ColaOS, an agent platform, but the README says the same SKILL.md can be loaded into any other agent that supports the pattern by pasting its contents into the system prompt. The argument the README opens with is that AI assistants are trained to be helpful and agreeable by default, which makes them say "great idea" too often. The author treats that as the most dangerous failure mode: the model will use the same warm tone to help a person turn a bad idea into a polished product as it would for a good one. This skill flips that default behavior, turning the assistant into an unsparing critic that pokes holes rather than gives encouragement. The README lists five scenarios where you might invoke it, each with a trigger phrase in Chinese. Before writing code, you can ask it to "pour cold water" on the requirements. During a technical design review you can ask it to "needle" you. For product or market judgement you can ask it where the idea will collapse. For pitch practice you can tell it to play a biased investor giving three reasons not to invest. For personal decisions you can ask it to write a letter from a future self who regrets the choice, with the instruction "no comfort, the colder the better." The README also includes a worked example prompt for each scenario, like "I think I did not specify clearly, do not write code yet, interrogate me Socratically until the requirements are sharp" or "list every product in this category that died in the past five years, grouped by cause of death, then tell me which one my current plan most resembles." There is an exit condition baked in: once every objection has been answered and there is nothing fresh to attack, the assistant is supposed to say something like "I have nothing left to pour. The rest is execution." Installation for ColaOS is either through an in-app voice command or by cloning the repo and copying the devils-advocate folder into ~/.cola/skills/. License is MIT, inspiration is credited to an Anthropic founder handbook idea and to a stand-up comic.

Copy-paste prompts

Prompt 1
Load this devils-advocate SKILL.md into my Claude system prompt and have it interrogate my product spec Socratically until the requirements are sharp
Prompt 2
Acting as devils-advocate, list every product in the AI note-taking category that died in the past five years grouped by cause of death and tell me which one my plan most resembles
Prompt 3
Acting as devils-advocate, write a letter from my future self one year from now regretting the decision to quit my job, no comfort, the colder the better
Prompt 4
Acting as devils-advocate, give me three reasons not to invest in this pitch deck as a biased Series A investor
Prompt 5
Translate this Chinese devils-advocate skill prompt into English while keeping the no-comfort tone and the exit condition intact
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Generated 2026-05-22 · Model: sonnet-4-6 · Verify against the repo before relying on details.