machiavelli-counsel

Machiavelli Counsel Skill

Five hundred years before "stakeholder management," Machiavelli wrote the unsentimental

manual on power: how it is gained, kept, and lost. This skill applies The Prince's

actual analytical questions to a modern workplace situation — then, because flattery

of the reader's cynicism is its own trap, pairs every Machiavellian read with the

honest modern move. You get the clear-eyed analysis without the 16th-century ethics.

What This Skill Produces

• A power map of the situation: who decides, who influences the decider, whose

support is load-bearing, who loses if you win

• A Machiavellian assessment — what The Prince's framework actually says about

your position (not generic "office politics tips")

• A counterweight plan: the ethical version of each move, and where the

Machiavellian and honest paths genuinely diverge

• A one-line fortuna check: what part of your position depends on luck holding

Required Inputs

Ask for (if not already provided):

• The situation, in the user's words (reorg, new boss, rival team, stalled project…)
• Who the key people are and what each controls (budget, headcount, the CEO's ear)
• What the user wants to happen, and by when
• What the user has already tried

Framework: the questions The Prince actually asks

Work through these five, in order — each is drawn from the book's recurring analysis:

1. New prince or established? (Ch. III, VI–VII) — Is the user (or their rival, or

the new leader) newly arrived in the role? New power is fragile: it must build its

own support and cannot rely on inherited loyalty. A new exec's first 90 days follow

Ch. III dynamics almost embarrassingly well.

1. Whose arms? (Ch. XII–XIII) — Does the user's position rest on their own

capability and relationships ("own arms"), or on a sponsor's protection

("auxiliaries")? Borrowed power vanishes with the sponsor. Name what is borrowed.

1. Feared, loved, or despised? (Ch. XVII, XIX) — Machiavelli's real claim is

narrower than the famous line: aim to be respected and above all avoid being

despised or resented — contempt, not strength, is what kills princes.

Translate: is the user seen as competent-and-fair, soft, or self-serving?

1. The friends of the old order (Ch. VI) — Who benefits from things staying as

they are? Change makes enemies of everyone the current arrangement feeds, and only

lukewarm allies of its beneficiaries-to-be. List both columns for the user's plan.

1. Fortuna vs virtù (Ch. XXV) — Roughly half of outcomes are outside anyone's

control; the skill of the operator is building levees before the river floods.

What is the user treating as stable that is actually luck?

Output Format

## The situation, read plainly
[2-3 sentences, no euphemism]

## Power map
| Person / group | Controls | Wants | Load-bearing for you? |

## The Machiavellian read
[Each of the five questions above, answered for THIS situation, chapter noted]

## Where Machiavelli is right — and where to ignore him
[The 2-3 insights that hold up · the moves he'd endorse that you shouldn't make,
and what to do instead. Be specific: "he'd say X; the durable version is Y."]

## The next two weeks
[3-5 concrete actions from the honest column]

## Fortuna check
[The one dependency that is luck, and its levee]

Quality Checks

• [ ] Every assessment traces to one of the five framework questions, chapter cited
• [ ] The power map includes at least one person the user didn't mention (asked for,

not invented) — the missing stakeholder is usually the story

• [ ] The counterweight section names a real divergence, not "be ethical" filler —

if the honest move and the Machiavellian move are the same, say so

• [ ] No invented quotes: paraphrase the book; quote only what you can quote exactly
• [ ] The advice would survive being read aloud to everyone named in it — that test

is itself the ethical line this skill holds

Anti-Patterns

• [ ] Do not recommend manipulation, deception, or briefing against colleagues — the

skill analyses power honestly; it does not coach bad faith. When the user asks

for the dark version, give the analysis and decline the execution.

• [ ] Do not serve generic office-politics advice ("build relationships!") wearing a

Machiavelli hat — every claim should need the book to make it

• [ ] Do not repeat the famous misquotes as the book ("the ends justify the means"

appears nowhere in it)

• [ ] Do not flatter the user's read of their own situation — Machiavelli's entire

value is that he didn't