devil-advocate

Identify counterarguments and diligence gaps against investment opportunities.

Updated Apr 24, 2026

Search Tags:#risk-management #investment-analysis #scenario-analysis #due-diligence #devil-advocate #adversarial-diligence

Ready to run

npx skills add https://github.com/intelligent-alpha/plugins --skill devil-advocate-intelligent-alpha

💬 Prompt for ChatGPT / Claude Chat▼

Please help me install this Agent Skill.
Skill: devil-advocate
Source: https://github.com/intelligent-alpha/plugins/tree/main/intelligent-alpha/skills/devil-advocate
Command: npx skills add https://github.com/intelligent-alpha/plugins --skill devil-advocate-intelligent-alpha

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This skill helps investment teams stress-test proposed deals by surfacing the strongest counterarguments and identifying gaps in diligence, reducing the risk of biased or rushed decisions.

Core Features & Use Cases

Articulates the strongest counterarguments against a deal and highlights weak assumptions to challenge the thesis.
Reads the family's rules and overlays to tailor adversarial prompts to the context and sensitivities.
Integrates with scenario-analysis to compare opposing viewpoints and prepare IC-level decisions.
Supports IC prep by surfacing a structured "no" case and recommended follow-up diligence items.

Quick Start

Provide the deal name and key assumptions, then ask the devil-advocate to generate the strongest counterarguments for the decision.

Frequently Asked Questions about devil-advocate

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

FAQPage Schema

How do I stress-test an investment thesis by generating counterarguments?▼

To stress-test an investment thesis, you provide the deal name and key assumptions to generate the strongest counterarguments, which highlight weak assumptions and surface diligence gaps to challenge the deal.

What is adversarial diligence and how does it support IC voting prep?▼

Adversarial diligence articulates the strongest cautions against an investment opportunity, surfacing a structured no case and recommended follow-up items to guide IC voting and red-team prep.

How do I identify gaps in investment due diligence before a deal decision?▼

You identify gaps in due diligence by applying adversarial analysis across diligence documents and scenarios, which surfaces cautions and counterarguments against the investment opportunity.

Can I tailor risk-management scenario analysis to specific family rules and overlays?▼

Yes, this approach reads family rules and overlays to tailor adversarial prompts to the context and sensitivities, ensuring scenario analysis aligns with specific investment parameters.

Does this approach work with existing diligence documents for red-team prep?▼

Yes, it applies across diligence documents and decision contexts to prepare IC-level decisions, reading per-skill context and citing sources to structure the red-team preparation.

When should I not use automated execution for investment scenario analysis?▼

You should avoid automated execution when performing adversarial diligence, as the approach requires reading family rules, overlays, and per-skill context while citing sources to maintain analytical integrity.