Personal Board Of Directors

Five standing advisors — the Operator, the Skeptic, the CFO, the Coach, the Customer — debate your decision on paper and vote. Use when asked to help me decide, pressure-test this decision, what would smart advisors say, or convene my board. Produces five distinct advisor memos, a disagreement map, a vote with a stated decision rule, and the one question to resolve before deciding.

Personal Board of Directors Skill

Good decisions survive five different kinds of scrutiny; most decisions get one (your own, on a good day). This skill convenes a standing board of five archetypes who each write a short memo, disagree where they honestly would, and vote — with the decision rule stated before the count.

What This Skill Produces

• Five advisor memos (~150 words each) in five genuinely different voices
• The disagreement map — where they split, and what fact would resolve each split
• The vote — with the decision rule declared first and what evidence would flip it
• The one question to answer before committing

Required Inputs

Ask for these if not provided:

• The decision — as a yes/no or A-vs-B; if it arrives vague ("should I do something about X?"), sharpen it into a decidable sentence first and confirm
• Stakes and reversibility — what's bet, and whether it can be undone
• Constraints — money, time, obligations, runway
• What the user is secretly hoping the answer is (optional — the board should know the bias it's correcting)

Framework: The Five Chairs

Advisor	Lens	Their memo must contain	Their known bias (they self-disclose it)
The Operator	Can this actually be executed, by you, now?	The first 2 weeks, resourced honestly	Overweights logistics, underweights vision
The Skeptic	Why this fails	The single most likely kill condition, dated	Kills some winners
The CFO	Unit economics of the choice	Real numbers from the input, or named missing ones	Discounts the unquantifiable
The Coach	Energy, growth, season of life	What this costs the person, not the plan	Overweights feelings
The Customer	Would the intended beneficiary care?	The beneficiary's likely verdict, in their words	Ignores the founder's needs

Decision rules (pick per stakes, state before voting): reversible + low stakes → simple majority · irreversible or high stakes → 4-of-5 supermajority · any advisor invokes a "stop-the-line" fact (a named, checkable disqualifier) → resolve that fact first, no vote.

Output Format

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Board Session: [the decision, one sentence]

Memos

[Five memos, each headed by the advisor, each ending "Vote: FOR / AGAINST / ABSTAIN — flips if: [named evidence]"]

Disagreement Map

Split	Advisors	The crux	What fact resolves it

The Vote

Decision rule: [stated + why] · Count: [n–n] · Board recommendation: … The one question to resolve first: [the highest-leverage unknown, and how to answer it cheaply this week]

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Quality Checks

• The five voices are distinguishable blind — cover the names and you can still tell who's who
• At least two advisors disagree, and the crux of the disagreement is named
• Every vote line names the evidence that would flip it
• The decision rule was stated before the count and matches the stakes
• The one question is answerable cheaply and quickly, not "do more research"

Anti-Patterns

• Do not let the advisors agree — forced consensus is the failure mode this skill exists to prevent
• Do not give all five the same voice with different hats — the CFO writes in numbers, the Coach doesn't
• Do not vote without naming what would flip each vote — an unflippable vote is a prejudice
• Do not let the board answer a vague question — sharpen it to decidable first
• Do not hide the recommendation in balance — the board exists to conclude, and the user can overrule it