Executive Mentor
Executive Mentor is an adversarial thinking partner for founders and executives. It stress-tests plans, prepares for brutal board meetings, dissects decisions with no good options, and forces honest post-mortems. The skill produces vulnerability assessments, board prep narratives, decision frameworks, assumption stress tests, and postmortem analyses.
✨ What it does
- Challenges plans with pre-mortem analysis and severity ratings.
- Prepares for board meetings by identifying hard questions and building narratives.
- Provides frameworks for hard calls like layoffs, pivots, and firings.
- Stress-tests assumptions with counter-evidence and downside modeling.
- Conducts honest post-mortems using 5 Whys and ownership assignments.
- Uses adversarial reasoning to find failure modes and warning signals.
🎯 When to use it
- When you have a plan you're excited about and need to find its weaknesses before others do.
- When a board meeting is approaching and you can't fully defend the numbers.
- When facing a decision you've been avoiding, especially with no good options.
- When something went wrong and you need an honest post-mortem without blame.
- When about to take an irreversible action and need to stress-test assumptions.
🚀 How to use
Trigger: /em:board-prep
Trigger with slash commands like /em:challenge <plan>, /em:board-prep <agenda>, /em:hard-call <decision>, /em:stress-test <assumption>, or /em:postmortem <event>. Provide the relevant plan, agenda, decision, assumption, or event as input. Example prompts:
/em:challenge Our Q3 GTM plan to expand into Europe
/em:board-prep Q2 board meeting agenda
/em:hard-call Whether to lay off 10% of staff
/em:stress-test We'll hit $2M ARR by December
/em:postmortem Why we lost the Acme deal
📄 Output: Deliverables include vulnerability reports, board prep briefs, decision frameworks, stress test analyses, and postmortem reports with action items.
📦 Add this skill to Claude Code
# 1. Get the skills repo
git clone --depth 1 https://github.com/alirezarezvani/claude-skills /tmp/claude-skills
# 2. Copy this skill into your project (or ~/.claude/skills for all projects)
mkdir -p .claude/skills
cp -r /tmp/claude-skills/c-level-advisor/executive-mentor/skills/executive-mentor .claude/skills/executive-mentorSkill source: c-level-advisor/executive-mentor/skills/executive-mentor/SKILL.md
⚠️ Good to know
This skill is not for validation or soft feedback; it is designed to be direct and uncomfortable, and it assumes you have a plan or decision to analyze.
❓ FAQ
What makes Executive Mentor different from other C-suite advisor skills?
It focuses on adversarial thinking and finding holes in plans rather than building them, asking questions you don't want to answer.
Can I use this skill for a decision I've already made?
No, it's not for validation; it's for stress-testing and preparing for hard questions.
What tools does it use?
It includes Python scripts for decision matrix scoring and stakeholder mapping.
🤖 Overview, features, install steps and FAQ were generated from the project's SKILL.md on Sep 4, 2026. Always check the original source before running commands.