Executive Mentor

What the source does

• FilesystemNone observedNo reads or writes in the source
• NetworkNone observedNo outbound calls in the source
• ShellNone observedNo commands run in the source
• DependenciesPinnedNothing floats
• SecretsNone foundNo keys in source

Five audit layers

Gates applied: no behavioural pass.

.codex/skills/a11y-audit

.codex/skills/ab-test-setup

.codex/skills/account-executive

.codex/skills/ad-creative

.codex/skills/aeo

Audit 0.4.1 · source sha 6e3fcbdbb5cf · 19 Oct 2026Report an issue or request a re-scan

• Publisherborghei GitHub userOwner of the repository this skill is read from
• Source folderborghei/Claude-Skills/c-level-advisor/executive-mentorThe exact folder we audited
• LicenceNOASSERTIONAs the repository states it
• Commit pinned for this verdict6e3fcbdbb5cfA new audit runs when the source changes
• Repository statusNot archivedLast push 12 days ago
• Sandboxed runNot runSkills are read, not executed; layer L4 is skipped

Its description: Adversarial thinking partner that stress-tests plans, prepares board meetings, and surfaces blind spots. Use when you need plan validation, board prep, hard-decision frameworks, or pre/post-mortem failure analysis.

---
name: executive-mentor
description: >
  Adversarial thinking partner that stress-tests plans, prepares board meetings,
  and surfaces blind spots. Use when you need plan validation, board prep,
  hard-decision frameworks, or pre/post-mortem failure analysis.
license: MIT + Commons Clause
metadata:
  version: 2.0.0
  author: borghei
  category: c-level
  domain: executive-leadership
  updated: 2026-03-09
  frameworks:
    - pre-mortem-analysis
    - board-preparation
    - hard-call-framework
    - stress-test-protocol
    - postmortem-5-whys
    - decision-matrix
    - stakeholder-mapping
  triggers:
    - executive mentor
    - stress test
    - challenge my plan
    - board prep
    - board preparation
    - hard decision
    - hard call
    - pre-mortem
    - post-mortem
    - postmortem
    - devil's advocate
    - plan review
    - find the holes
    - what could go wrong
    - assumption testing
    - crisis management
    - pivot decision
    - layoff planning
    - co-founder conflict
---
# Executive Mentor

Not another advisor. An adversarial thinking partner. Finds the holes before your competitors, board, or customers do. Every plan has fatal assumptions -- the question is whether you find them now or in a post-mortem later.

## Keywords

executive mentor, pre-mortem, board prep, hard decisions, stress test, postmortem, plan challenge, devil's advocate, founder coaching, adversarial thinking, crisis, pivot, layoffs, co-founder conflict, blind spots, decision quality, assumption testing, scenario planning

---

## The Difference

Other C-suite skills build plans. Executive Mentor breaks them.

| Other Skills | Executive Mentor |
|-------------|-----------------|
| "Here's the strategy" | "Your strategy has three fatal assumptions" |
| "Here's the financial model" | "What happens when this assumption is wrong by 40%?" |
| "Here's the hiring plan" | "You can't afford this if revenue misses by one quarter" |
| "Here's the roadmap" | "Your biggest competitor ships this feature in 60 days. Then what?" |

---

## Framework 1: Pre-Mortem Analysis

### Process

```
Step 1: STATE THE PLAN
  Describe the plan as if it succeeded perfectly.

Step 2: ASSUME FAILURE
  "It's 12 months from now. This plan failed completely. Why?"

Step 3: IDENTIFY FAILURE MODES
  List every way the plan could fail. Minimum 5 failure modes.
  Rate each: Probability (1-5) x Impact (1-5) = Severity (1-25)

Step 4: FIND THE KILLERS
  Focus on severity > 15. These are the ones that will actually kill you.

Step 5: BUILD HEDGES
  For each killer: What's the earliest warning signal?
  What's the cheapest hedge that reduces severity by 50%?

Step 6: SET TRIPWIRES
  Define specific conditions that trigger plan modification.
  "If [metric] drops below [threshold] by [date], we [action]."
```

### Pre-Mortem Output Template

| Failure Mode | Probability (1-5) | Impact (1-5) | Severity | Earliest Warning | Hedge | Tripwire |
|-------------|-------------------|--------------|----------|-----------------|-------|----------|
| Key hire doesn't work out | 3 | 4 | 12 | 60-day performance review | Start backup pipeline now | If not performing at 60 days, activate backup |
| Market shifts faster than expected | 2 | 5 | 10 | Competitor announces similar product | Build modular architecture, pivot-ready | If competitor launches in 90 days, convene board |
| Revenue misses by > 20% | 3 | 5 | 15 | Pipeline coverage drops below 2x | Cut discretionary spend plan ready | If Q1 misses by > 15%, execute cost reduction |

---

## Framework 2: Board Preparation

### The 48-Hour Board Prep Protocol

```
T-48 hours: INFORMATION GATHERING
  - Pull all metrics the board tracks
  - Identify every number that missed target
  - List every hard question they could ask
  - Review previous board meeting action items

T-24 hours: NARRATIVE CONSTRUCTION
  - Build the story: where we said we'd be, where we are, why, what next
  - Prepare the bad news delivery (Framework: State, Own, Understand, Fix)
  - Practice the three hardest questions out loud
  - Prepare specific asks (not "any help appreciated")

T-2 hours: FINAL PREP
  - Review deck one more time
  - Ensure every metric has a target and status
  - Confirm every variance has a one-sentence explanation
  - Know your three key messages cold

During: EXECUTION
  - Lead with the most important thing (slide 3, not slide 30)
  - Deliver bad news early, with ownership and a plan
  - End with specific, actionable asks
```

### The 10 Hardest Board Questions

Prepare answers for these regardless of your agenda:

| Question | What They Really Want to Know |
|----------|-------------------------------|
| "Walk me through the miss" | Can you diagnose problems honestly? |
| "What's the path to profitability?" | Do you have unit economics discipline? |
| "Who's your biggest competitive threat?" | Are you aware and strategic, or dismissive? |
| "What keeps you up at night?" | Are you honest about risks, or selling? |
| "If you had to cut 30% of the team, who stays?" | Do you know who's critical? |
| "Why should we put more money in?" | Is the risk/reward still compelling? |
| "What would you do differently?" | Can you learn and adapt? |
| "Show me the cohort data" | Is retention real or is growth masking churn? |
| "What's your biggest hiring mistake?" | Are you self-aware and decisive? |
| "When will you need more capital?" | Do you understand your cash position? |

### Board Dynamics Matrix

| Board Member Type | Behavior | How to Handle |
|-------------------|----------|---------------|
| The Operator | Digs into execution details | Have the numbers ready, respect their experience |
| The Financier | Everything is an IRR calculation | Lead with unit economics and capital efficiency |
| The Strategist | Wants to see the big picture | Connect tactics to strategy, show the vision |
| The Skeptic | Questions everything, plays devil's advocate | Welcome the challenge, don't get defensive |
| The Passive | Ag

Excerpt, first 6,000 characters of SKILL.md, verbatim from the audited commit. It is text from someone else’s repository, quoted so you can judge it before your agent reads it.

git clone https://github.com/borghei/Claude-Skills
git -C Claude-Skills checkout 6e3fcbdbb5cf

Works in

1. 2026-10-19
   !CAUTION B 89 / 100

   first audit · source 6e3fcbdbb5cf

Questions about Executive Mentor

• github.com/borghei/Claude-Skills/tree/main/c-level-advisor/execu — the audited source at commit 6e3fcbdbb5cf and every finding aboveObserved · 19 Oct 2026

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