strategy-self-critique

Critique strategy assumptions against failure modes and market data monthly.

Updated Apr 19, 2026
One-click install
npx skills add https://github.com/marmikcfc/pepper-skills --skill strategy-self-critique
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: strategy-self-critique
Source: https://github.com/marmikcfc/pepper-skills/tree/main/skills/strategy-self-critique
Command: npx skills add https://github.com/marmikcfc/pepper-skills --skill strategy-self-critique

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Strategy blind spots and untested assumptions can derail planning. This Skill performs a monthly red-team of the current strategy against failure modes and market data to surface risks and push for hard conclusions.

Core Features & Use Cases

  • Monthly critique: stress-test the strategy against failure modes, channels, and market signals to reveal riskiest assumptions.
  • Context integration: aggregates data from strategy/strategy.md, strategy/learnings.md, reviews/weekly/, metrics/retention/, and experiments/archive/* to inform the critique.
  • Output for planning: writes a formal critique to strategy/critique.md to guide quarterly planning and leadership decisions.

Quick Start

Run the monthly critique to generate the strategy critique and save it to strategy/critique.md.

Frequently Asked Questions about strategy-self-critique

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

FAQPage Schema
How do I run a red-team critique to find blind spots in my strategy?

To run a red-team critique, aggregate data from strategy, learnings, weekly reviews, retention metrics, and experiments to stress-test assumptions against failure modes and market signals. The output is a formal critique written to strategy/critique.md to guide planning.

What is a monthly strategy critique and when do I need it?

A monthly strategy critique is a red-team process that surfaces untested assumptions and risks by analyzing failure modes against market data. You need it during monthly planning cycles to prevent strategy blind spots from derailing your quarterly goals.

What inputs are required to stress-test strategy assumptions?

Required inputs include strategy/strategy.md, strategy/learnings.md, reviews/weekly/*, metrics/retention/*, and experiments/archive/*. The critique aggregates these files to analyze failure modes and inform quarterly planning decisions.

Can I use this red-team critique for quarterly planning?

Yes, the monthly red-team critique is explicitly designed to inform quarterly planning. By surfacing the riskiest assumptions and writing them to strategy/critique.md, leadership receives hard conclusions for decision-making.

How does a red-team critique handle risk analysis and market data?

The critique integrates retention metrics and experiment archives to stress-test current strategy against market signals and failure modes. It pushes for hard conclusions by revealing the riskiest assumptions across monthly planning cycles.

Are there limitations to using monthly reviews for risk analysis?

This critique relies on existing files like strategy/learnings.md and reviews/weekly/*, so it cannot surface risks if those inputs are missing or outdated. It functions best when integrated across monthly planning cycles with continuous data.