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.
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Use personal-board-of-directors to evaluate [decidable decision] using [stakes, reversibility, and constraints], producing five advisor memos, a disagreement map, a stated-rule vote, and the one question to resolve before deciding.
Required inputs
[decidable decision]
[stakes, reversibility, and constraints]
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SKILL.md
name: personal-board-of-directorsdescription: "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
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]
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