Analyse a workplace power situation the way Machiavelli's The Prince (1532) would — who holds power, whose support you need, what fortune can take from you — then give both the Machiavellian read and the honest modern counterweight. Use when navigating a reorg, a new leader arriving, stakeholder politics, a territory dispute, or 'my project is caught in politics'. Produces a power map, a Machiavellian assessment, and an ethical playing-it-straight plan.
Scanned 9/3/2026
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---
name: machiavelli-counsel
description: "Analyse a workplace power situation the way Machiavelli's The Prince (1532) would — who holds power, whose support you need, what fortune can take from you — then give both the Machiavellian read and the honest modern counterweight. Use when navigating a reorg, a new leader arriving, stakeholder politics, a territory dispute, or 'my project is caught in politics'. Produces a power map, a Machiavellian assessment, and an ethical playing-it-straight plan."
---
# 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.
2. **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.
3. **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?
4. **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.
5. **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
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