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