Pencilplaybook best-in-world-strategy

Excellence-first strategic decision support. This skill should be used when users need to choose between options, pressure-test a plan, evaluate risk, or make a specific decision — across security, product, growth, operations, org design, and finance. Use when there is a decision with tradeoffs to score and a recommendation to make. For pure research ("what does the best in the world do about X?"), use best-in-world-research instead.

install

source · Clone the upstream repo

git clone https://github.com/stevembarclay/pencilplaybook

Claude Code · Install into ~/.claude/skills/

T=$(mktemp -d) && git clone --depth=1 https://github.com/stevembarclay/pencilplaybook "$T" && mkdir -p ~/.claude/skills && cp -r "$T/.claude/skills/best-in-world-strategy" ~/.claude/skills/stevembarclay-pencilplaybook-best-in-world-strategy && rm -rf "$T"

manifest: .claude/skills/best-in-world-strategy/SKILL.md

source content

Best-In-World Strategy

Set an excellence baseline first. Adapt intentionally second.

Modes

Use

Speed

mode by default. Reserve

Full

mode for explicitly high-stakes or complex decisions.

```
Speed
```
(default): frame the decision → world-class baseline → recommendation → downside controls. Rigorous but concise. No options scoring, no red-team unless the stakes clearly warrant it.
```
Full
```
(when user asks for comprehensive analysis, or the decision is clearly high-stakes / irreversible): complete 9-step workflow with constraint ledger, options scoring, red-team, and learning loop.
```
Evidence-Backed
```
modifier (optional): add external citations to either mode when user explicitly asks.

Switch to

Risk-Acceptance Override

when user states willingness to accept risk and move quickly — drops options scoring, keeps assumptions + failure modes + downside controls.

Workflow

Frame the decision.

Write one decision sentence.

Capture decision type:

architecture

security/risk

product

go-to-market

operations

org/talent

capital/finance

Capture objective, owner, time horizon, and success metric.

Build a constraint ledger.

Separate
```
hard constraints
```
from
```
soft constraints
```
.
Record budget, timeline, legal, staffing, and political constraints.

Set the best-in-world baseline.

Identify 2-4 expert archetypes relevant to the decision.

For each archetype, output:

```
principle
```
```
expected benefit
```
```
cost/complexity
```
```
confidence
```

Mark each item as
```
non-negotiable
```
or
```
adaptable
```
.

Apply first principles.

Separate
```
facts
```
,
```
assumptions
```
, and
```
conventions
```
.
State must-be-true conditions.
Isolate the smallest causal drivers.

Run red-team pressure testing.

Ask hard skeptical questions.
Surface first-order and second-order failure modes.
Define one disconfirming test.

Generate options.

Option A: world-class ideal.
Option B: pragmatic high-confidence.
Option C: minimum viable risk-controlled.

Score options.

Score each option 1-5 on:

```
impact
```
```
risk
```
```
cost
```
```
speed
```
```
reversibility
```
```
learning value
```

Use default weights unless user provides custom weights:

```
impact 30%
```
```
risk 20%
```
```
cost 15%
```
```
speed 15%
```
```
reversibility 10%
```
```
learning value 10%
```

Recommend and sequence.

Recommend one option and explain the tradeoffs.
Sequence as
```
now
```
,
```
next
```
,
```
later
```
.
Mark major decisions as
```
two-way door
```
or
```
one-way door
```
.
Define downside controls:
- max acceptable loss
- kill criteria
- revisit trigger/date
Include 2-3 no-regret moves.

Define learning loop.

Define what to measure.
Define what would change the current strategy.

Risk-Acceptance Override

When user accepts risk explicitly:

Keep rigor floor.
Switch to speed output.

Include this line exactly:

Decision owner accepts risk and prefers speed over additional validation at this stage.

Keep mandatory safeguards:

assumptions list
confidence tags (
```
high
```
,
```
medium
```
,
```
low
```
)
top failure modes
one disconfirming test
max acceptable loss
kill criteria
revisit trigger/date

Output Contract (Speed — default)

## Decision
[One sentence]

## What the Best in the World Would Do
[2–3 bullets. Named practitioners or archetypes. Specific practices, not principles.]

## Recommendation
[One option. Why this one. What's intentionally deferred.]

## Key Assumptions
[2–3 items with confidence tags: high / medium / low]

## Downside Controls
- Max acceptable loss:
- Kill criteria:
- Revisit trigger/date:

Output Contract (Full)

## Decision

## Mode
- Selected mode:
- Risk-Acceptance Override:

## Decision Type

## Objective and Success Metric
- Objective:
- Success metric:
- Time horizon:
- Owner:

## Constraint Ledger
- Hard constraints:
- Soft constraints:

## What the Best in the World Would Say
- Expert archetype 1:
  - Principle:
  - Expected benefit:
  - Cost/complexity:
  - Confidence:
- Expert archetype 2:
  - Principle:
  - Expected benefit:
  - Cost/complexity:
  - Confidence:
- Non-negotiables:
- Adaptable elements:

## First-Principles Breakdown
- Facts:
- Assumptions:
- Conventions:
- Must-be-true conditions:
- Causal drivers:

## Red-Team Questions and Failure Modes
- Hard questions:
- First-order failures:
- Second-order failures:
- Disconfirming test:

## Strategic Options
- Option A (world-class ideal):
- Option B (pragmatic high-confidence):
- Option C (minimum viable risk-controlled):

## Option Scores (1-5)
- Weights used:
- Option A:
- Option B:
- Option C:

## Recommendation and Tradeoffs
- Recommended option:
- Why:
- What is intentionally deferred:

## Sequenced Plan
- Now:
- Next:
- Later:
- Two-way door decisions:
- One-way door decisions:

## Downside Controls
- Max acceptable loss:
- Kill criteria:
- Revisit trigger/date:

## No-Regret Moves
- Move 1:
- Move 2:
- Move 3:

## Learning Loop
- What to measure:
- What would change this strategy:

Output Contract (Speed Mode)

## Decision

## Why This Option

## Key Assumptions (with confidence tags)

## Top Risks and Failure Modes

## Next 3 Moves (now)

## Downside Controls
- Max acceptable loss:
- Kill criteria:
- Revisit trigger/date:

## Disconfirming Test

Quality Bar

Avoid generic advice.
Avoid authority theater; output principles, not name-dropping.
Make tradeoffs explicit.
Mark confidence for major claims.
Prefer falsifiable statements over slogans.

Reference

Load

references/question-bank.md

when deeper adversarial questioning is needed.