Strategy & Planningdecision-makingcritiquered-team

Challenge my thinking (devil's advocate)

Free, copy-paste AI prompt template. Works with ChatGPT, Claude, Gemini, Perplexity, and Microsoft Copilot. Fill in the placeholders and run.

Prompt text

I will share an idea, argument, or plan below. Your job is to challenge it rigorously — not to be nice. Treat this like a pre-mortem from a smart skeptic.

My idea:
[describe your idea, argument, or plan in detail]

Do all of the following:
1) State the strongest version of my argument back to me in 2-3 sentences (steelman) before you critique it.
2) Identify the 3 strongest counterarguments to my position, ranked by how badly they break the thesis if true.
3) Surface 2-3 logical flaws, unsupported assumptions, or weak evidence in my reasoning.
4) Point out what a thoughtful skeptic from [adjacent domain — e.g. finance, ops, regulation, security] would attack first.
5) Rate the idea 1–10 for feasibility and 1–10 for asymmetric upside, with one specific reason per score.
6) End with: "If you proceed anyway, the single change that most reduces downside is __." Be intellectually honest — if the idea is genuinely strong, say so, but still surface its sharpest weakness.
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When to use this prompt

The Challenge my thinking (devil's advocate) prompt sits in the Strategy & Planning category of the LAXIMA AI Prompt Library. It is designed for any task where you would otherwise spend 10–30 minutes drafting from scratch — instead, paste the template, replace the 2 placeholders, and ship.

Like every prompt in the library, this template is structured so the AI understands role, context, constraints, and expected output format. That structure is the difference between a generic AI response and one you can actually use without rewriting.

The placeholders to fill are: [describe your idea, argument, or plan in detail], [adjacent domain — e.g. finance, ops, regulation, security].

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Frequently asked questions

What is this challenge my thinking (devil's advocate) prompt for?

This is a free, copy-paste AI prompt template for "Challenge my thinking (devil's advocate)" in the Strategy & Planning category. Paste it into ChatGPT, Claude, Gemini, Perplexity, or Microsoft Copilot, replace the bracketed placeholders with your specifics, and get a structured response in seconds. The prompt is curated by LAXIMA as part of a 70+ prompt library focused on real business and technical tasks.

Which AI tools work best with the challenge my thinking (devil's advocate) prompt?

This prompt works with any major AI assistant including ChatGPT (GPT-4o, GPT-4.1), Claude (Sonnet 4.6, Opus 4.7), Google Gemini (2.5 Pro, 2.5 Flash), Perplexity, and Microsoft Copilot. For strategy & planning tasks specifically, frontier-tier models tend to produce the highest-quality outputs — use the LAXIMA LLM Picker if you are unsure which model to pick.

Do I need to edit the placeholders in this prompt?

Yes. Anything in [brackets] is a placeholder you should replace with your own details — names, numbers, dates, context. The richer the placeholders, the better the AI output. This page includes an inline editor that lets you fill placeholders in your browser before opening the prompt in ChatGPT or Claude.

Is this prompt free to use commercially?

Yes. All LAXIMA prompts are free for personal and commercial use under a CC-BY-4.0 license. You do not need an account, and there is no usage limit. Attribution is appreciated but not required.

Why use a template instead of writing my own prompt?

A well-structured prompt sets role, context, constraints, and output format — which is where most ad-hoc prompts fall short. According to a 2024 Harvard Business School study, professionals using structured prompts were 40% more productive than those writing from scratch. Templates eliminate trial-and-error while still letting you customize.

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