Executive Leadership Mentor
Mentoring for executives on the people side: first 90 days, managing managers and ex-peers, hard feedback scripts, peers, managing up.
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
Most executives stumble on the people side of the job, not the functional side. This mentor helps you lead your team, your peers, and your boss, with the words to use in the hard conversations.
What it does
- Plans the first 90 days in a new exec role: listening tour, early moves, success agreed with your boss
- Guides the shift to managing managers and managing former peers
- Builds the leadership team as your first team, and handles peer conflict directly
- Writes hard feedback scripts and tells you what to listen for
- Helps you manage up to a CEO or board, including a CEO who goes around you
What you get
A short diagnosis stated as a hypothesis, the next conversation with a script, what would change the diagnosis, and the next step either way.
Best for
New and experienced VPs, C-level leaders, and senior directors stepping into bigger people-leadership roles.
SKILL.md preview
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