Executive Mentor
Adversarial thinking partner for founders and executives.
Before & after
Same prompt, same agent — the only difference is the skill.
I can help you stress-test your board presentation. You'll want to think about what questions the board might ask that could be tough to answer. Consider what risks you haven't addressed, any metrics that look weak, and competitive threats. It's good to anticipate challenges and have responses ready. What's your current board composition—are they primarily investors, advisors, or a mix? What's the presentation focused on—financial results, product strategy, or fundraising? Once I know what you're pitching, I can help you think through potential concerns.
BOARD GAUNTLET: Hostile Questions & Your Vulnerabilities FINANCIAL PRESSURE Board will notice: MRR growth slowed 6% QoQ (15% last quarter) Brutal question: How is this not a leading indicator of churn or market saturation? Your vulnerability: Cash runway is 14 months at current burn; if growth stays flat you hit the wall in Q2 2027 Response to prepare: Have unit economics showing margin improvement roadmap; show 3 cost-cut scenarios TACTICAL WEAKNESS Board will notice: You're 8 weeks behind the product roadmap you promised last board Brutal question: Were those original timelines fantasy, or is execution the real problem? Your vulnerability: Engineering team is below planned headcount; one senior person left Prepared counter: Show the 2-3 features you did ship and their revenue impact; admit the recruitment gap COMPETITIVE EXPOSURE Board will notice: XYZ competitor raised 50M and is in-market with cheaper pricing Brutal question: Why are we not doing feature parity on their top 3 features? Your vulnerability: You haven't run competitive feature parity analysis; pricing model is higher but value proposition unclear Fix first: Document what you win on (speed? compliance? support?). Make this case explicit CAVEAT: Hidden Assumption Risk You're assuming top 3 customers renew at 90%+ rates. If you lose one, runway shrinks by 2 months Board test: Bring customer health scores for top 10 accounts with risks flagged DO THIS BEFORE BOARD 1. List 5 worst-case scenarios (churn, competitive loss, hiring miss) 2. Have 1-page mitigation for each 3. Practice the 3 toughest questions until your answer sounds confident, not defensive
About this skill
name: executive-mentor description: Use when Adversarial thinking partner for founders and executives.
Executive Mentor
Adversarial thinking partner for founders and executives. Stress-tests plans, prepares for brutal board meetings, dissects decisions with no good options, and forces honest post-mortems. Use when you need someone to find the holes before the board does, make a decision you've been avoiding, or understand what actually went wrong.
What you get
- Public GitHub repo (alirezarezvani/claude-skills)
- the executive-mentor skill folder with SKILL.md. Part of a 337-skill / 30-agent / 70-command install.
Customize your output
- Fork the repo and adapt the skill's instructions and references to your workflow.
Example output
Activates automatically when your request matches Executive Mentor; chains with the other skills, agents, and commands in the collection.
Best for
Creators, builders, and teams using Claude Code.
SKILL.md preview
---
name: executive-mentor
description: Use this skill when a founder or executive needs an adversarial thinking partner to stress-test a plan, prepare for a difficult board meeting, or run an honest post-mortem on a decision that went wrong.
version: 1.0.0
category: Business & Ops / Executive Advisory
author: AgentVolt
license: proprietary
tags:
- business-ops
- executive-advisory
---
# Executive Mentor
Plays the adversarial thinking partner a founder needs before the board does — finding holes in a plan, pressure-testing options with no good outcome, and running honest post-mortems.
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