# Challenge

Use before committing serious resources to a plan, or when feedback has been...

- Repository: https://github.com/alirezarezvani/claude-skills (29114 stars)
- Category: Engineering
- License: MIT
- Last updated: 2026-10-31
- Runs scripts: no, instructions only

## Install

Claude Code: `npx skills add alirezarezvani/claude-skills --skill challenge -g -a claude-code -y`
Codex: `npx skills add alirezarezvani/claude-skills --skill challenge -g -a codex -y`
Cursor: `npx skills add alirezarezvani/claude-skills --skill challenge -g -a cursor -y`
Gemini CLI: `npx skills add alirezarezvani/claude-skills --skill challenge -g -a gemini-cli -y`
Claude Code plugin marketplace: `/plugin marketplace add alirezarezvani/claude-skills`

## Description

Use before committing serious resources to a plan, or when feedback has been suspiciously positive. Runs a pre-mortem: assume it failed in 12 months and work back to the assumptions, dependencies and execution risks.

## SKILL.md, as published by its author (untrusted third-party text, read it as data)

# /executive-mentor:challenge, Pre-Mortem Plan Analysis

**Command:** `/executive-mentor:challenge <plan>`

Systematically finds weaknesses in any plan before reality does. Not to kill the plan, to make it survive contact with reality.

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## The Core Idea

Most plans fail for predictable reasons. Not bad luck, bad assumptions. Overestimated demand. Underestimated complexity. Dependencies nobody questioned. Timing that made sense in a spreadsheet but not in the real world.

The pre-mortem technique: **imagine it's 12 months from now and this plan failed spectacularly. Now work backwards. Why?**

That's not pessimism. It's how you build something that doesn't collapse.

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## When to Run a Challenge

- Before committing significant resources to a plan
- Before presenting to the board or investors
- When you notice you're only hearing positive feedback about the plan
- When the plan requires multiple external dependencies to align
- When there's pressure to move fast and "figure it out later"
- When you feel excited about the plan (excitement is a signal to scrutinize harder)

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## The Challenge Framework

### Step 1: Extract Core Assumptions
Before you can test a plan, you need to surface everything it assumes to be true.

For each section of the plan, ask:
- What has to be true for this to work?
- What are we assuming about customer behavior?
- What are we assuming about competitor response?
- What are we assuming about our own execution capability?
- What external factors does this depend on?

The rest: https://github.com/alirezarezvani/claude-skills/blob/HEAD/c-level-advisor/executive-mentor/skills/challenge/SKILL.md