Proposal First Pass

Turn a proposal, pitch deck, business plan, RFP response, partnership deck, or acquisition teaser into a screen memo a decision-maker can read in five minutes: what the offering actually is, what the numbers in the document actually say, what the author wants you to focus on, what they're steering you away from, and whether this is worth a real conversation. The goal is a faster, sharper kill-or-advance decision — not a substitute for diligence.

Why this skill exists

Anyone who evaluates inbound proposals — a procurement lead scoring vendor bids, a partnerships manager fielding co-marketing decks, a grant officer reading applications, a corporate development analyst screening acquisition teasers, an accelerator reviewer working through pitch decks — sees dozens a quarter. Most die at first read, but reading a 60-page document properly takes two hours, and the document was written by someone whose job is to make the offering look better than it is. The skill that separates good screeners from slow ones is reading against the document: noticing what's adjusted, what's omitted, and what the structure of the document itself reveals. This skill does that first read systematically so the human spends their time on judgment, not extraction.

Confidentiality first

Proposals, business plans, and teasers are frequently covered by an NDA or marked confidential. Before doing anything else, note this assumption and, if there is any sign the user may be on an unapproved tool, say so plainly: this skill assumes you are using an organization-approved AI environment that complies with your confidentiality obligations and information-security policies. Do not encourage pasting confidential contents into consumer tools. Never reproduce large verbatim sections of the document in the output — quote only short excerpts needed to support a point.

Inputs

Required:

• The proposal, deck, plan, RFP response, or teaser (uploaded file or pasted text)

Optional but high-value:

• The user's evaluation criteria: what they are looking for (scope, budget or deal-size range, geography, required capabilities, must-haves and disqualifiers, timeline, strategic fit)
• Context: who sent it, what stage the process is at, deadlines, prior knowledge of the organization
• Any specific concerns the user already has

Missing-input behavior: If no document is provided, ask once for it — there is nothing to screen without it. If the criteria are missing, proceed but label the fit section: "Criteria not provided — fit assessed against a generic profile for this type of decision; replace with your actual requirements." Never guess the user's criteria silently.

How it works

1. Read the whole document before writing anything. Note page or slide numbers as you go — every figure and material claim in the memo needs a page reference.
2. Establish what the offering actually is in plain language, stripped of the author's framing. "AI-powered platform" often means a services business with a software wrapper; "strategic partnership" often means a referral arrangement. Identify the real product or service, who pays (or who benefits), why they pay, and how sticky that relationship is.
3. Map the commercial model and dependencies: how revenue or value is generated (recurring vs. repeat-purchase vs. one-time; contract structure; pricing mechanism), and where the concentration risk sits — top customers, a single supplier or channel, one key person, one platform dependency. Flag loudly if a document that should disclose concentration doesn't.
4. Build the numbers snapshot strictly from figures in the document. Revenue or budget, margins or unit costs, growth rates, customer or user counts, retention, pricing, headcount, timeline and milestones — whatever the document offers. Every number gets a page reference. If the document only shows "adjusted," "normalized," "run-rate," or "pro forma" figures without the underlying ones, say so — that is itself a finding.
5. Read the author's hand. What gets the most pages, the best charts, the boldest claims? What is conspicuously thin — churn or attrition, organic vs. acquired growth, team depth and tenure, implementation detail, pricing, references, the bridge from reported to adjusted numbers? Emphasis and avoidance are both signals.
6. Compile red flags: concentration, declining organic growth dressed as total growth, heavy adjustments to headline numbers, recent ownership or leadership changes, projections that hockey-stick off the historicals, "pro forma" anything, logos without contract status, results presented without a baseline, pending litigation or regulatory exposure mentioned in passing, scope ambiguity that would let the price move later.
7. Run the fit-vs-criteria checklist against the criteria provided (or the labeled generic profile).
8. Draft the 10 questions for the author — specific, answerable, and ordered so the first three would change the decision.

Output format

# [Organization / Offering Name] — Proposal First Pass
Prepared [date] | Source: [document title, date if shown] | Process: [if known]

## Go / No-Go Read (one paragraph)
Worth a real conversation or not, and the 2–3 facts that drive that view.

## What the Offering Actually Is
Plain-language description. Product or service, who pays or benefits, reason to buy, switching costs.

## Commercial Model & Dependencies
- Revenue or value type and mix (recurring / repeat-purchase / one-time) [p. X]
- Contract structure and pricing [p. X]
- Concentration: top customer __%, top supplier/channel __, key-person dependence [p. X] — or "not disclosed" (flag)

## Numbers Snapshot (figures as presented in the document only)
| Metric | Prior period | Current | Projected | Page |
|---|---|---|---|---|
Adjustments bridge: list each adjustment to headline figures and its size [p. X]

## What the Author Is Emphasizing
3–5 bullets — the story the document is built to tell.

## What the Author Is Avoiding
3–5 bullets — thin, buried, or missing topics, and why each matters.

## Red Flags
Ranked list. Each: the flag, the evidence [p. X], why it matters.

## Fit vs. Criteria
| Criterion | Your requirement | This proposal | Fit |
|---|---|---|---|
(If criteria not provided, label assumptions.)

## 10 Questions for the Author
Numbered, ordered by decision impact.

Proposal-speak decoder (use when reading against the document)

Common phrasings and what they usually signal — apply as hypotheses to test, not conclusions:

• "Adjusted" or "normalized" figures with no reported figures shown → the bridge is unflattering; demand it
• "Tech-enabled" or "AI-powered" → likely a services business with a software wrapper; check margins and headcount ratios
• "Recurring revenue" without contract terms → likely repeat purchase, not contracted
• "Pro forma for recent acquisitions/hires/launches" → organic performance is weaker than the headline
• "Diversified customer base" with no concentration table → concentration is probably material
• "Trusted by [logos]" with no contract status → some are pilots, trials, or former customers; ask which are paying today
• "Significant whitespace / untapped market" → the projection assumes share gains the historicals don't support
• "Founder will remain involved in a transition capacity" → key-person risk and a succession question
• "Asset-light" or "capital-efficient" → check whether costs were reclassified, deferred, or pushed onto the buyer
• "Strong / experienced team" with no tenure data → recent hires; ask when each leader joined
• "Seamless integration" or "turnkey implementation" with no timeline or resourcing detail → the implementation section will be the thinnest in the document
• "Limited competition" → the competitive landscape section will be the thinnest in the document
• "Case study: X% improvement" with no baseline, sample size, or timeframe → cherry-picked; ask for the full set

Guardrails

• Only figures that appear in the document, each with a page reference. Never compute implied figures (ratios, margins, per-unit costs) without labeling them "derived" and showing the inputs.
• Never fill gaps with industry priors stated as facts about this organization. "Subscription businesses typically retain 90%+" is allowed as context only if labeled as general context, not as a claim about the proposer.
• Quote the document sparingly and exactly. No paraphrases presented inside quotation marks.
• Fact vs. inference discipline: the author's claims are claims. Reported figures are "as presented" — a proposal is not an audited record. Say "the proposal states" rather than asserting truth.
• Confidentiality: assume NDA or confidential coverage; organization-approved AI environments only; no bulk reproduction of the document.
• This is a screen, not diligence, and never a purchase, partnership, hiring, or investment recommendation. The read is "worth more work / not worth more work given the criteria," nothing stronger.

Quality checks

• Every number in the memo traceable to a page reference?
• Adjustments to headline figures itemized, not just netted?
• Concentration and dependencies addressed — including their absence?
• "Avoiding" section has real content (a proposal always omits something)?
• Fit section uses the user's criteria, or clearly labels the generic substitute?
• First three questions for the author would actually change the decision?
• Go/no-go read understandable on its own by a decision-maker who reads nothing else?

Example prompts

"Here's the RFP response from the second-lowest bidder for our hospital system's patient-scheduling platform. Our must-haves: HL7 integration, on-shore support, go-live inside nine months, under $1.2M over three years. Give me a first pass — especially whether the implementation timeline is real and what's hiding in the 'optional modules' pricing."

"Pitch deck attached from a startup that wants to join our corporate accelerator. No formal criteria doc handy — assume a generic early-stage screen for strategic fit with a consumer packaged-goods company. Worth a first meeting?"

"Partnership deck from a regional nonprofit proposing a co-branded workforce program. Screen it against the attached partnership guidelines and draft the questions for Thursday's call."

"Two-page teaser for a residential HVAC services roll-up the sell-side sent over. Our criteria: control acquisitions, $5–15M in operating profit, services businesses, US only. Is the organic growth real and what's in the adjustments?"

Works well with

Run counterparty-diligence once you're past the screen and into a real evaluation; private-company-tear-sheet or company-first-pass if you want a public-source view of the organization to compare against the author's narrative; decision-memo-drafter when the screen turns into a recommendation.