Executive Mentor

Description

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 this skill does

1. 1Challenges any plan by identifying assumptions, rating their confidence, mapping dependencies, and listing numbered vulnerabilities by severity.
2. 2Prepares executives for adversarial board meetings by surfacing the ten hardest questions, identifying data gaps, and building a narrative that acknowledges weakness without losing the room.
3. 3Structures decisions with no good options using reversibility testing, the 10/10/10 framework, and stakeholder impact mapping.
4. 4Stress-tests specific assumptions — revenue projections, moat claims, market size estimates — by surfacing counter-evidence and modeling the downside.
5. 5Runs post-mortems with 5 Whys done without softening, separating contributing factors from root cause and assigning owners per required change.

When to use

• A plan you are excited about needs someone to find the holes before the board does.
• A board meeting is within two weeks and you cannot fully defend your numbers.
• A decision has been avoided for weeks and needs to be made despite no good options.
• Something went wrong and the post-mortem has not happened yet or has been too diplomatic.