the-org-simulator

The Org Simulator Skill

Org changes are designed on the box-and-line level and experienced on the

who-do-I-report-to-now level. The gap between those two is where reorgs fail:

the map made sense, but the two best engineers quit, the middle managers went

quiet, and the memo leaked on Tuesday before the Thursday announcement. This

skill simulates the experienced version before the announced version exists —

seat by seat for the key people, faction by faction for the rest, plus the

one test almost nobody runs: reading the memo as the person it demotes, on a

screenshot, out of context.

What This Skill Produces

• A winners / losers / undecided map — by named seat for key people, by

group for the rest: what each actually loses or gains (scope, status,

access, headcount, identity), not what the memo says they gain

• A friction forecast: the 5–8 specific breakpoints of the first 90 days,

each with likelihood, blast radius, and the cheap preventative

• The leak test: the announcement read as a screenshot by its least

charitable reader, plus what the corridor version of it will say by Friday

• A sequenced rollout plan: who hears it in which order, from whom, with

the one question each conversation must answer

Required Inputs

Ask for (if not already provided):

• The change: current structure → proposed structure, and the honest why

(the memo-why and the real-why, if different — the simulation needs both)

• The key seats affected: names/roles, current scope, and what's known of

their ambitions and frustrations

• History that shapes reception: previous reorgs and how they went, standing

rivalries, recent departures

• Timing and constraints: what's fixed, what's still movable, who already knows

Process

1. Simulate seats, not boxes. For each key person: scope Δ, status Δ

(title, audience, room access), boss Δ, identity Δ ("am I still the

platform person?"). Losses count double — people fight losses harder than

they chase gains. Mark each seat: champion / accepter / quiet-resister /

flight-risk, with the because.

1. Find the undecideds. The middle managers and senior ICs who could go

either way decide reorg outcomes; list who they'll ask about it in the

first 24 hours — those people, not the memo, are the actual communication

channel.

1. Forecast friction concretely. Not "there may be resistance" but "the

two platform leads now share one headcount pool and will collide at

Q3 planning". For each: likelihood, blast radius, the cheap preventative

available before announcement (a scope clarification, a title fix, a

pre-conversation).

1. Run the leak test. Rewrite the draft announcement's message as

received by its least charitable reader from a screenshot with no

context, no Q&A, no follow-up meeting. If the leaked version is fatal,

the announcement isn't ready. Then write the corridor version — the one

sentence people will actually repeat — and check it's survivable.

1. Sequence the rollout. Order: losers first, privately, from someone

they trust (hearing it in the all-hands is how flight-risks convert) →

undecideds' influencers → champions armed with the honest FAQ → everyone.

Each conversation gets the one question it must answer for that hearer.

Pressure-test the final plan against [[machiavelli-counsel]]'s friends-of-

the-old-order column if politics run deep.

Output Format

## The change in one line (memo-why · real-why)

## Seat map
| Seat | Scope Δ | Status Δ | Reads as | Champion/Accepter/Resister/Flight-risk | Because |

## The undecided middle
[Who they are · who they'll ask in the first 24h]

## Friction forecast — first 90 days
| # | Breakpoint (specific) | Likelihood | Blast radius | Cheap preventative |

## Leak test
[The screenshot read, least charitable voice · the corridor sentence ·
verdict: survivable / fix before announcing]

## Rollout sequence
| Order | Who | From whom | The one question this conversation must answer |

Quality Checks

• [ ] Every key seat's read includes a because grounded in scope/status/

identity — no one is labelled a resister without a stated loss

• [ ] At least one friction item the user hadn't foreseen (probe the shared-

resource collisions and the title deltas — that's where they hide)

• [ ] The leak test uses the least charitable reading, not the intended one,

and issues a verdict

• [ ] Losers hear it first and privately in the rollout, or the plan argues

explicitly why not

• [ ] The simulation stays a planning tool: predictions are labelled as

predictions about reactions, not verdicts on people

Anti-Patterns

• [ ] Do not simulate boxes ("Team A reports to B") — simulate Tuesday

morning for the person whose title just got shorter

• [ ] Do not let the memo-why hide the real-why from the simulation; people

react to the real-why they infer, not the memo-why they're given

• [ ] Do not use the seat map as a loyalty dossier — it plans communication,

not retaliation; decline that turn if asked

• [ ] Do not skip the leak test because "it won't leak" — the test costs ten

minutes and reorg memos leak at a rate that rounds to always

• [ ] Do not end without the preventatives — a friction forecast with no

cheap fixes is just organized dread

Related

[[machiavelli-counsel]] for the power analysis under this; [[change-management-plan]]

for the full formal program; [[stakeholder-influence-mapper]] for the influence

graph the rollout sequence rides on.