challenge

challenge is a skill for Claude Code from alirezarezvani/claude-skills. It costs 77 tokens per session (1,530 once invoked), scanned A, original, MIT.

A challenge skill associated with executive mentoring.

In plain words
What is it for?
It is intended for testing assumptions in decisions or plans.
Why use it?
It may provide constructive questioning or pushback, but the available description does not explain how it works.

Skill for Claude Code

Written for Claude Code: shipped in a Claude Code plugin.

Part of the executive-mentor plugin — 6 skills, 1 agent shipped together

Good fit It is intended for testing assumptions in decisions or plans.

Compare 6 skills from other repositories ↓
Install with agentmods
npx agentmods add skills/alirezarezvani/claude-skills/challenge
About the project

claude-skills is a large collection of reusable skills, commands, plugins, and supporting resources for coding agents across engineering, business, research, compliance, and productivity work. It is used by people who want agents such as Claude Code, Codex, Gemini CLI, or Cursor to follow specialized workflows. The catalogue contains selected skills and settings from the collection.

alirezarezvani/claude-skills · 28,607 stars · on GitHub · alirezarezvani.medium.com

Install

Getting it into your agent

One page per mod, every tool's command on it. A separate URL per tool would split the same page into five that compete with each other.

Any agent
npx skills add alirezarezvani/claude-skills --skill challenge
Clone the repo
git clone --depth 1 https://github.com/alirezarezvani/claude-skills

Made for: Claude Code.

Or install executive-mentor, the plugin that ships this one along with the rest of its 6 skills, 1 agent.

Wrote this? Show the measurements

A badge with what this costs and how it scanned, read live from this page, so it follows the numbers instead of freezing them. Markdown for a README, HTML for a documentation site or a project page.

agentmods badge for challenge

README.md
[![agentmods](https://agentmods.dev/badge/skills/alirezarezvani/claude-skills/challenge/github.svg)](https://agentmods.dev/skills/alirezarezvani/claude-skills/challenge)
Your own site
<a href="https://agentmods.dev/skills/alirezarezvani/claude-skills/challenge"><img src="https://agentmods.dev/badge/skills/alirezarezvani/claude-skills/challenge/github.svg" alt="Measured on agentmods" height="20"></a>

Or the 80×15 button, for a site that already has a row of RSS and ATOM ones. Only the verdict fits; the numbers stay here.

agentmods 80×15 button for challenge

Your own site · 80×15
<a href="https://agentmods.dev/skills/alirezarezvani/claude-skills/challenge"><img src="https://agentmods.dev/badge/skills/alirezarezvani/claude-skills/challenge.svg" alt="Reviewed on agentmods" width="80" height="20"></a>
Per session 77 Skills are progressive disclosure: only the name and description are preloaded; the body loads when the skill is used.
When invoked 1,530 The whole file, excluding the scripts and references it only reads on demand.
Security scan A 0 findings. A grade says what 26 rules found in the file — not that it is safe. Third-party audits
  • Socket pass 18 Sept 2026
  • Snyk pass 18 Sept 2026
  • NVIDIA SkillSpector warn 7 Sept 2026
SkillSpector: 1 finding, up to medium

These are SkillSpector’s own severities. On a checked sample its high-severity flags on skills were ~96% false positives — a documented command, a public API, a “never do X” rule — so we show them as a caution to read, not a verdict. Why →

  • medium Agent Snooping · line 1
    Skill enumerates or reads other installed skills. Access to other skills' SKILL.md files or the skills directory reveals prompt instructions, capabilities, and secrets that should be invisible to peer skills.
    Fix: Remove all code or instructions that list or read other skills' files or directories. Skills should operate independently; cross-skill access is a privilege escalation.
How audits are shown
Origin original No closer match found in the catalogue.
Token cost

What it costs to keep this loaded

Counted locally with the o200k_base tokenizer, which is exact for GPT models; Claude uses its own tokenizer and its counts differ. Treat this as one consistent yardstick across the catalogue rather than a bill. Prices are per million input tokens.

ModelPer sessionOnce invoked
Fable 5.1 $0.00077 $0.01530
Opus 5.5 $0.00031 $0.00612
Sonnet 5.5 $0.00015 $0.00306
Haiku 4.5 $0.00008 $0.00153

Measured today against content hash eb04f1e49bae, method: parsed. Prices are Anthropic first-party input rates as of 2026-10-07, from the pricing page.

Security

Grade A, and why

challenge scanned grade A with 0 findings against 26 rules in 11 categories — prompt injection, anti-refusal, data exfiltration, privilege escalation, supply chain, agent snooping, system-prompt leakage, SSRF and excessive agency — measured today.

A static scan of the body, not an audit. Every finding is printed with the line that produced it so you can judge whether it matters here. A mod is markdown that instructs an agent; that is exactly why what it instructs is worth reading.

Nothing flagged

None of the 26 patterns this scan looks for appear in this file: no shell pipes, no recursive deletes, no credential paths, no hidden text, no instruction-override or anti-refusal phrasing, no agent-config snooping. That is not a guarantee, it is the absence of the things that are checkable.

Origin

Copies of this mod

2 near-identical copies found in the catalogue:

  • challenge — 100% identical, 183 lines differ
  • challenge — 100% identical, 183 lines differ
c-level-advisor/executive-mentor/skills/challenge/SKILL.md · 182 lines

How it starts

The opening of the file, as written. The whole thing — 182 lines — stays where its author put it; the contents beside it link to each section on GitHub.

/em:challenge — Pre-Mortem Plan Analysis

Command: /em:challenge <plan>

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


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.


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)

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?

Common assumption categories:

  • Market assumptions — size, growth rate, customer willingness to pay, buying cycle
  • Execution assumptions — team capacity, velocity, no major hires needed
  • Customer assumptions — they have the problem, they know they have it, they'll pay to solve it
  • Competitive assumptions — incumbents won't respond, no new entrant, moat holds
  • Financial assumptions — burn rate, revenue timing, CAC, LTV ratios
  • Dependency assumptions — partner will deliver, API won't change, regulations won't shift

Read the full file on GitHub · 182 lines

Changes

What this file has done since we first saw it

Hashed on every crawl. A supply-chain change to an agent config is a question of when, not whether, so the history is kept rather than the latest state alone.

  1. today Changed · +181 lines · +77 tokens per session eb04f1e49bae
  2. 1mo ago First seen · 1 lines · 0 tokens per session scan A d56303f02a82

Subscribe to this mod's changes

challenge is a skill published in the GitHub repository alirezarezvani/claude-skills (28,607 stars, last pushed yesterday), licensed MIT. It adds 77 tokens to every session and 1,530 once invoked, about $0.0003 per session on Opus 5.5. A static security scan graded it A with 0 findings. No closer match exists in the catalogue, so it is treated as the original; first seen 2026-09-03.

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