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devil-advocate

Challenge optimistic conclusions and generate a Devil's Advocate risk report.

Updated Jan 22, 2026

Search Tags:#portfolio #risk-analysis #investing #due-diligence #devil-advocate #assumption-challenge #scenario-inversion

Ready to run

npx skills add https://github.com/ByungJu-Lim/obsidian-- --skill devil-advocate-byungju-lim

💬 Prompt for ChatGPT / Claude Chat▼

Please help me install this Agent Skill.
Skill: devil-advocate
Source: https://github.com/ByungJu-Lim/obsidian--/tree/main/0-Projects/honeypot-main/honeypot-main/plugins/investments-portfolio/skills/devil-advocate
Command: npx skills add https://github.com/ByungJu-Lim/obsidian-- --skill devil-advocate-byungju-lim

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

The Devil's Advocate skill systematically challenges every positive conclusion to reveal hidden risks and reduce overconfidence in investment analyses.

Core Features & Use Cases

Robust assumption testing: prompts that surface untested premises.
Scenario exploration: generates counterfactuals and worst-case views to stress-test decisions.
Risk framing and documentation: outputs a structured report highlighting risks and recommended actions.

Quick Start

Ask for the strongest counter-argument after reviewing an investment thesis to surface hidden risks.

Frequently Asked Questions about devil-advocate

High-intent search queries and answers about installing and using this skill.

FAQPage Schema

How do I challenge investment assumptions to reveal hidden risks?▼

To challenge investment assumptions, you systematically test positive conclusions by generating counterfactuals and worst-case scenarios, which surfaces untested premises and reduces overconfidence in your portfolio analysis.

What is assumption testing in portfolio risk analysis?▼

Assumption testing in portfolio risk analysis is the process of identifying and questioning untested premises in an investment thesis, ensuring robust decision-making by surfacing hidden risks before finalizing asset allocations.

How do I run a devil's advocate review on a fund selection?▼

Running a devil's advocate review on a fund selection involves prompting for the strongest counter-arguments after reviewing your thesis, then formatting the results into a structured report with risk flags and recommended actions.

Can I use scenario inversion to stress-test my asset allocation?▼

Yes, you can use scenario inversion to stress-test asset allocation by generating worst-case views and counterfactuals, which helps document risk factors and evaluate the robustness of your investment decisions.

When do I need a counterfactual analysis for my investing due diligence?▼

You need counterfactual analysis for investing due diligence after reviewing sector outlooks or fund selections, ensuring you surface hidden risks and challenge optimistic conclusions before finalizing your portfolio decisions.

What is the best way to document worst-case scenarios for investment risk?▼

The best way to document worst-case scenarios for investment risk is to use a structured fillable report that highlights assumption challenges, risk flags, and repeatable evaluation steps to ensure robust decision-making.