Proposal Skeleton

Proposal Skeleton Skill

Internal proposals die of three causes: the problem arrived unpriced (so the status quo stayed free), the options section was a strawman parade (so the reader felt managed), or the ask was unsized (so "interesting" substituted for a decision). The working spine is old and undefeated: the problem with its cost → real options fairly stated → the recommendation with reasons → risks conceded with mitigations → a decision-sized ask with a reversibility line. One page, because proposals are read in the gap between meetings.

What This Skill Produces

• The filled skeleton — problem-with-cost, options, recommendation, risks, ask — from the actual case
• The objections table — the three likely objections, pre-answered in the reader's dialect
• The ask, decision-sized — what exactly, costing what, decided by whom, reversible how
• The one-page version — with the appendix rule for everything that overflows

Required Inputs

Ask for these if not provided:

• The change and the evidence — what's being proposed and what supports it (the pilot data, the incident, the quote comparisons); skeletons organize evidence, not enthusiasm
• The cost of the status quo — the number or consequence that makes "do nothing" a choice with a price; without it, inertia wins by default and deserves to
• The decision-maker and their dialect — who says yes, and what they weigh (money? risk? team health?) — the recommendation argues in their currency (executive-summary audience rules apply)
• The honest alternatives — including the strongest version of "do nothing" and the rival option a smart skeptic would raise

Framework: The Spine Rules

1. Price the problem first: "we spend ~11 hours/week on manual reconciliation (≈ $2.9k/month)" converts the proposal from a preference into arithmetic — and do-nothing from the safe default into the most expensive option on the page. Honest numbers only; one inflated cost discounts the whole case.
2. Options are steelmanned or they're theater: 2–3 real options, each with its genuine best case — including do-nothing's ("zero switching cost, no adoption risk"). Readers detect strawmen instantly, and a fairly-stated rival makes the recommendation more credible, not less.
3. Recommend with reasons that touch the comparison: "Option B, because it fixes the cost at 40% of Option C's price and reverses in a month if wrong" — the recommendation cites the dimensions the options table established, in the decision-maker's currency.
4. Concede risks before the reader finds them: the objections table — likely objection → honest answer or mitigation — signals the thinking survived contact with skepticism. A proposal with no stated risks reads as either naive or salesy; both lose.
5. The ask is decision-sized and reversibility-framed: "Approve a 6-week pilot for one team at $X, success = [metric], full rollout decided after" — small enough to say yes to today, with the exit named. Big irreversible asks get deferred forever; pilots get approved this week. The one-page rule: spine on page one, everything else (the vendor matrix, the data) appendixed and referenced.

Output Format

Proposal: [the change] — for [decision-maker]

The Problem, Priced

[Two sentences + the honest number/consequence of continuing]

Options (steelmanned)

Recommendation

[The option + the reasons in the reader's currency + the reversibility line]

Objections, Pre-Handled

The Ask

[Exactly what · costing what · decided by whom, by when · pilot-sized with the success metric and exit]

(Appendix: the overflow — referenced, not inlined)

Quality Checks

• The status quo carries an honest price
• Every option including do-nothing got its best case
• The recommendation argues in the decision-maker's stated currency
• Risks are conceded with mitigations before the reader raises them
• The ask is pilot-sized, dated, and names its reversal path

Anti-Patterns

• Do not propose against an unpriced status quo — free inertia beats every paid change
• Do not strawman the alternatives — the detected strawman costs more credibility than the rival option ever would
• Do not ask for the end-state — ask for the smallest decidable step toward it
• Do not hide the risks — the reader's discovered objection beats your conceded one, in their favor
• Do not exceed a page in the body — the appendix exists so the spine can breathe