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Home › AI prompts › Work › AI prompt to review a business proposal before you send it

AI prompt to review a business proposal before you send it

Published October 16, 2026

WritingBusiness
Linocut of a magnifying glass with a blue lens lying on a proposal, the way an AI prompt reviews a proposal before you send it.

This AI prompt reads your proposal through the eyes of the person getting it. It ranks the 5 reasons they’d turn you down and points to the part of your proposal behind each one.

Then it tells you the one thing that would get a yes, and rewrites your opening around it.

Use it before you send a proposal, a quote or a pitch to a client, your boss, or anyone you’re trying to convince.

Why read your proposal the way they will

I write proposals all the time, and I always read them through my own biased lens. In my head, I know what I mean. The person getting it doesn’t have the background I have. They’re busy, and they have other offers on the table.

And they’re going to run it through AI themselves and ask which proposal is best. You might as well see what AI is going to tell them first.

How to use this proposal review prompt

Paste the prompt into a new chat. It asks you 4 questions, one at a time:

  1. Who’s going to read it? A client, your boss, or anyone else you’re trying to convince.
  2. What problem are they trying to solve? Paste their email word for word if you have it.
  3. What else are they comparing you to, and roughly what does it cost?
  4. A few lines you wrote yourself, so the rewrite sounds like you.

Then paste the proposal. Part 1 gives you the 5 reasons they’d say no. Type “next” and Part 2 tells you what to change.

The prompt that reads your proposal like they will

I'm about to send a proposal, and I want to know why it might get turned down before the person reading it tells me. This runs in 2 parts. Never start Part 2 until I type "next."

Ask me these questions one at a time. Wait for my answer before you ask the next one.

1. Who's going to read it? A client, a prospect, your boss? What do they do?
2. What problem are they trying to solve? Paste their email or message in their own words if you have it.
3. What else are they comparing your proposal to, and roughly what do those options cost?
4. Can you paste a few lines of something you wrote yourself, like an email or a past proposal? I'll use it to match your voice later.

Then ask me to paste the proposal.

Part 1. Become that reader. You're busy, a little skeptical, and you have other options on the table. Read the proposal once, the way you really would.

Give me the 5 reasons you'd turn it down or stop replying. For each reason, quote the line in the proposal that caused it. If the reason is something missing, say what's missing. If you can't tie a reason to the proposal, leave it out. Don't be polite, and don't suggest fixes yet.

Mark each reason as one of these, and rank them in this order:
- Deal-breaker: I'd stop reading here.
- Doubt: I'd keep reading, but trust you less.
- Nitpick: I'd notice it, but it wouldn't change my answer.

End Part 1 with this exact line and nothing after it:
Type "next" for Part 2.

Part 2. When I type "next," stay in character and tell me the one thing that would make you say yes today.

Then step out of character. For each of the 5 reasons, give me the one change that would remove it, in my words from the writing sample.

Last, rewrite the first 2 sentences of my proposal around the one thing that gets a yes. Match my writing sample, not a polished business tone. If I didn't give you a sample, keep as many of my original words as you can.

Why it works: Every reason has to quote a line from your proposal or explain what’s missing. This stops it from inventing objections that could fit any proposal. The deal-breaker, doubt and nitpick labels tell you which 1 or 2 to fix first.

One gap: It only knows the reader through what you give it. Describe their problem from memory and it reads your guess, not what they said.

Simple fix: Paste their email word for word. Their exact words are what it argues from.

Prompt writing tips you can use anywhere

Each tip is a line from the prompt above. Copy the line into your own prompts, then read why it’s there.

1. Tie every answer to something real

For each reason, quote the line in the proposal that caused it. If the reason is something missing, say what's missing. If you can't tie a reason to the proposal, leave it out.

Without this line, AI invents objections that could fit any proposal. Use it any time you want feedback on something real. Swap “proposal” for your resume, your cover letter or your landing page.

2. Give the ranking a rule

Mark each reason as one of these, and rank them in this order:
- Deal-breaker: I'd stop reading here.
- Doubt: I'd keep reading, but trust you less.
- Nitpick: I'd notice it, but it wouldn't change my answer.

Ask AI to rank things with no rule and the order comes out random. The labels tell it what “worse” means, and they tell you what to fix first.

3. Make it stop between parts

This runs in 2 parts. Never start Part 2 until I type "next."
End Part 1 with this exact line and nothing after it:
Type "next" for Part 2.

Gemini Flash ran both parts at once. Saying “2 parts” up front and giving the exact last line fixed it. Use this whenever you want to read one answer before AI moves on.

4. Give it a sample of your writing

Can you paste a few lines of something you wrote yourself, like an email or a past proposal? I'll use it to match your voice later.
Match my writing sample, not a polished business tone.

A Reddit commenter pointed out that the rewrite drifted into a polished AI tone. A few lines of your own writing pull it back to how you talk. This works for any rewrite, not just proposals.

5. Ask for one change per problem

For each of the 5 reasons, give me the one change that would remove it, in my words from the writing sample.

A list of problems tells you what’s wrong. One change per problem tells you what to do about it.

6. Ask about the reader first

Ask me these questions one at a time. Wait for my answer before you ask the next one.

The questions let the same prompt work for a client, a prospect or your boss. One at a time, you answer each one properly instead of skimming a list.

Want a second read on the rest of your work? The honest feedback prompt does that for anything you’re about to send. Proposal still a voice memo? Start with the voice memo proposal prompt.

Original post by u/join2nitesh on r/ChatGPTPromptGenius. Link

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Contents

  • Why read your proposal the way they will
  • How to use this proposal review prompt
  • The prompt that reads your proposal like they will
  • Prompt writing tips you can use anywhere
  • 1. Tie every answer to something real
  • 2. Give the ranking a rule
  • 3. Make it stop between parts
  • 4. Give it a sample of your writing
  • 5. Ask for one change per problem
  • 6. Ask about the reader first

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In this article

  • Why read your proposal the way they will
  • How to use this proposal review prompt
  • The prompt that reads your proposal like they will
  • Prompt writing tips you can use anywhere
  • 1. Tie every answer to something real
  • 2. Give the ranking a rule
  • 3. Make it stop between parts
  • 4. Give it a sample of your writing
  • 5. Ask for one change per problem
  • 6. Ask about the reader first

Frequently asked questions

How do I find out why my proposal might get turned down?

Find out why your proposal might get turned down by asking AI to read it as the person who will get it. Tell it who they are, paste their email in their own words, and name the other options they’re comparing. Then ask for the 5 reasons they’d say no, each tied to a line in your proposal.

Can AI review a proposal for a client, a prospect or a boss?

AI can review a proposal for a client, a prospect or a boss. The prompt in this post asks who will read it first, so the same prompt works for a sales pitch, a quote or an internal request.

Why does AI make up objections to my proposal?

AI makes up objections to your proposal when nothing forces it to point at the page. Add one line: for each reason, quote the line in the proposal that caused it, or say what’s missing. If it can’t tie a reason to the proposal, it leaves it out.

How do I stop AI from rewriting my proposal in a stiff business tone?

Stop AI from rewriting your proposal in a stiff business tone by pasting a few lines you wrote yourself, like an email or a past proposal. Then tell it to match that sample, not a polished business tone.

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