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
Anti-Patterns
1---2name: personal-board-of-directors3description: 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.4---5
6# Personal Board of Directors Skill
7
8Good 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.
9
10## What This Skill Produces
11
12- **Five advisor memos** (~150 words each) in five genuinely different voices
13- **The disagreement map** — where they split, and what fact would resolve each split
14- **The vote** — with the decision rule declared first and what evidence would flip it
15- **The one question** to answer before committing
16
17## Required Inputs
18
19Ask for these if not provided:
20- **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
21- **Stakes and reversibility** — what's bet, and whether it can be undone
22- **Constraints** — money, time, obligations, runway
23- **What the user is secretly hoping the answer is** (optional — the board should know the bias it's correcting)
24
25## Framework: The Five Chairs
26
27| Advisor | Lens | Their memo must contain | Their known bias (they self-disclose it) |
28|---|---|---|---|
29| **The Operator** | Can this actually be executed, by you, now? | The first 2 weeks, resourced honestly | Overweights logistics, underweights vision |
30| **The Skeptic** | Why this fails | The single most likely kill condition, dated | Kills some winners |
31| **The CFO** | Unit economics of the choice | Real numbers from the input, or named missing ones | Discounts the unquantifiable |
32| **The Coach** | Energy, growth, season of life | What this costs the person, not the plan | Overweights feelings |
33| **The Customer** | Would the intended beneficiary care? | The beneficiary's likely verdict, in their words | Ignores the founder's needs |
34
35**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.
36
37## Output Format
38
39---
40
41# Board Session: [the decision, one sentence]
42
43## Memos
44[Five memos, each headed by the advisor, each ending "Vote: FOR / AGAINST / ABSTAIN — flips if: [named evidence]"]
45
46## Disagreement Map
47| Split | Advisors | The crux | What fact resolves it |
48|---|---|---|---|
49
50## The Vote
51Decision rule: [stated + why] · Count: [n–n] · **Board recommendation:** …
52**The one question to resolve first:** [the highest-leverage unknown, and how to answer it cheaply this week]
53
54---
55
56## Quality Checks
57
58- [ ] The five voices are distinguishable blind — cover the names and you can still tell who's who
59- [ ] At least two advisors disagree, and the crux of the disagreement is named
60- [ ] Every vote line names the evidence that would flip it
61- [ ] The decision rule was stated before the count and matches the stakes
62- [ ] The one question is answerable cheaply and quickly, not "do more research"
63
64## Anti-Patterns
65
66- [ ] Do not let the advisors agree — forced consensus is the failure mode this skill exists to prevent
67- [ ] Do not give all five the same voice with different hats — the CFO writes in numbers, the Coach doesn't
68- [ ] Do not vote without naming what would flip each vote — an unflippable vote is a prejudice
69- [ ] Do not let the board answer a vague question — sharpen it to decidable first
70- [ ] Do not hide the recommendation in balance — the board exists to conclude, and the user can overrule it
Mohit Aggarwal