Someone on r/PromptEngineering turned a simple brainstorming trick into an installable skill, and the way it got there is the interesting part.
u/wtfzambo had a draft architecture for a project and couldn’t think of any alternatives. Normal move: ask ChatGPT what it thinks and get a cheerful “ABSOLUTELY!” back. Useless when you want to find holes.
The twist: they changed the job, not the model. They told the AI to “play devil’s advocate and tear my idea apart.” It went so well that they packaged the whole thing as a skill, so the same process runs every time without retyping the prompt. The repo is github.com/wtfzambo/devils-advocate.
The unexpected bit is that the win isn’t a clever prompt. It’s turning a one-off prompt that worked into something repeatable. Most of us find a good prompt, use it once, and lose it in chat history.
Here’s the mini-workflow:
- 🧱 Write your draft idea, plan, or architecture in plain words.
- 🎭 Tell the AI to play devil’s advocate and tear it apart. Don’t ask “what do you think?”
- 🔍 Read the objections and sort them: real risks, or noise.
- 🔁 When it works for you, save the pattern as a skill so you can run it again next time.
Pro tips from the thread:
- Give it enough context first. One commenter said they tried this on a design doc and it caught three failure modes they’d missed. But without context, it just nitpicks edge cases that will never happen.
- Give it a concrete job instead of a vague role. Another commenter likes prompts like “list the 3 most likely ways this design fails in 6 months, ranked by probability.” A job with a ranking beats “be critical.”
The post only has 4 upvotes, so this is a small drop. But it’s a cheap thing to try. Pick something you’re about to commit to, run it through the devil’s advocate treatment, and see what survives. I’d rather hear the ugly objections from an AI today than from production in six months!
Grab the skill, try it on your next plan, and tell the author how it went. 🚀
Frequently Asked Questions
Q: How much context should I give before asking for devil’s advocate feedback?
Give the model enough background first, including your constraints, your goals, and what you have already tried. One commenter found that without that context, the model just nitpicks edge cases that will never happen. Once it knows the stakes, its objections get much more useful.
Q: Is a vague ‘play devil’s advocate’ prompt enough, or should I give it a specific job?
Some users get better results from a concrete task than from a role. Ask for the three most likely ways your design fails in six months, ranked by probability, and for each one, what you would notice first. That last part turns vague worries into warning signs you can actually watch for.
Q: What if the alternative you rejected was the better choice?
Ask the model to argue for the best option you dropped, as if it had to defend it to your team. This often surfaces the tradeoff you skipped past. If the alternative still loses after that, you can explain why in one sentence and trust the decision more.
Pro tip: ask AI to play devil’s advocate when brainstorming.
by u/wtfzambo in PromptEngineering