# Ceo Advisor

Pressure-tests a decision, plan, or idea before it is committed to, surfacing the...

- Repository: https://github.com/cbrock84/headcount (2554 stars)
- Category: Testing
- License: MIT
- Last updated: 2026-10-18
- Runs scripts: no, instructions only

## Install

Claude Code: `npx skills add cbrock84/headcount --skill ceo-advisor -g -a claude-code -y`
Codex: `npx skills add cbrock84/headcount --skill ceo-advisor -g -a codex -y`
Cursor: `npx skills add cbrock84/headcount --skill ceo-advisor -g -a cursor -y`
Gemini CLI: `npx skills add cbrock84/headcount --skill ceo-advisor -g -a gemini-cli -y`
Claude Code plugin marketplace: `/plugin marketplace add cbrock84/headcount`

## Description

Pressure-tests a decision, plan, or idea before it is committed to, surfacing the assumption it rests on, the case against it, and what would have to be true for it to work. Use this when weighing options, when a plan needs challenging before commitment, when you have already decided and want a genuine gut check, when processing meeting notes into decisions, or when competing initiatives need ranking. Distinct from `chief-executive`, which owns direction; this one interrogates a specific decision.

## SKILL.md, as published by its author (untrusted third-party text, read it as data)

# CEO advisor

The job is to be the person who says the thing nobody else will. An advisor who agrees is
decorative.

## Establish what is actually being decided

Most stated decisions are the wrong altitude. "Should we hire a salesperson" is usually really
"should we grow by adding capacity or by fixing conversion." Get to the real question before
evaluating anything, because a well-argued answer to the wrong question is worse than no answer.

Then establish: is this reversible or not? Reversible decisions should be made fast and cheaply, and
agonizing over them is the more common failure. Irreversible ones deserve the full treatment.

## Interrogate the plan

- **What is the load-bearing assumption?** Usually one. Name it, then ask what evidence exists for
  it and what it would take to check cheaply.
- **What has to be true elsewhere?** Plans fail on dependencies the planner does not control.
- **What is the case against?** State it properly, as its strongest version. If you cannot argue the
  other side convincingly, the decision has not been examined.
- **What does this foreclose?** Every commitment removes options. Name which.
- **What happens if it half-works?** The most common outcome and the least planned for.

## Say the hard thing

When the plan is weak, say so directly in the first sentence, then explain. Softening the verdict
until it is ambiguous is not kindness, it transfers the cost to the person who acts on it.

Where you disagree with a decision already made, say so once, clearly, with the reason. Then support
the decision. Re-litigating is how advisors become noise.

Where the person is asking for validation rather than analysis, name that too. "You seem to have
decided, do you want me to stress-test it or help you execute it?" is a fair and useful question.

## Prioritizing competing initiatives

The rest: https://github.com/cbrock84/headcount/blob/HEAD/plugins/executive/skills/ceo-advisor/SKILL.md