I’ve lost count of the times I’ve sat in front of a blank Word doc late at night, trying to turn messy notes into something a client or investor would actually read. So this post from a founder-focused AI professional hit close to home. It’s a simple fix for a problem almost everyone has.
The author opens with a line that stings a little: most founders write every important document twice. They write it once in a rush, then again at 11pm, when it actually matters. Proposals, investor updates, hiring plans and policies nobody wants to read all start the same way, with a blank page and a blinking cursor.
Why AI in Word often makes things worse
The original poster says most people using AI in Word make the problem worse. They type one lazy line and get back generic, robotic copy. Then they spend an hour making it sound human again. The time saver ends up costing time.
The creator admits to falling into that trap too. A proposal used to take them most of a day. Now it takes one focused hour, and the result reads better. They kept the same tools and the same Word document. The tool didn’t change. The approach did: they started treating AI like a sharp editor instead of a ghostwriter.
You stay the author. The AI handles the outline, the tightening and the checking.
I love this framing because it fixes the biggest problem with AI writing. Your ideas, facts and voice stay yours. The AI does the boring work around them. That’s the idea behind the 20 prompts in the post, and they work with Copilot in Word, Claude for Microsoft 365 and ChatGPT for Word.
The 10 prompts worth starting with
The expert shared 20 prompts and picked out ten as the best place to begin. Here’s each one, with a quick note on why it helps.
- Plan and draft: Get a full outline with word counts before you write a line. You lock in the structure early, so you’re not moving sections around at midnight.
- Mark the gaps: The AI puts [ADD] wherever your own facts belong. It doesn’t make up numbers. This is the best defense against confident AI hallucinations sneaking into a client proposal.
- Rewrite and improve: Shorter sentences, active voice, same meaning. It’s useful when a draft is technically correct but reads like a legal memo.
- Change the tone: You get two versions, one light touch and one full rewrite. Comparing them side by side makes it much easier to choose than asking for a single “better” version.
- Cut it down: Hit your word count without losing the call to action. Most people trim the wrong parts. This keeps the ask intact.
- Proofread: Every error goes into a table, and your style stays untouched. You see exactly what changed and why, instead of the AI quietly rewriting your voice.
- Get honest feedback: A 1 to 10 score from a tough but fair reader. It’s a cheap way to stress-test a doc before a real investor or client sees it.
- Format it: Headings, tables and a table of contents in one pass. That’s 30 minutes of fiddly clicking gone.
- Extract actions: Every owner, deadline and decision in one table. This is perfect for meeting notes and long project docs where tasks get buried.
- Repurpose it: Turn the doc into an email, an FAQ or a one-page brief. You write once and use it in three places.
The underrated one: prompt 16
This is the one I’d bookmark. The post’s author calls prompt 16 underrated, and I agree. You give it two versions of a contract or proposal. It lists every change in meaning, not just wording. Then it flags anything that could create a legal, financial or reputational risk.
The creator says it’s the one they’d want before signing anything. If you’ve ever had a counterparty “just tweak a few lines” in a contract, you know why. Small wording changes can move liability, payment terms or deadlines without anyone saying so. An AI second pass won’t replace a lawyer, but it’s a great early warning system.
Where to start on your next proposal
The advice from this savvy professional is to start with prompt 2. On your next proposal, give the AI your outline and notes, and let it mark every gap with [ADD].
You’ll see how much faster a first draft comes together when nothing is made up. Instead of fact-checking every sentence, you fill in the blanks. Your real numbers, client names and timelines go exactly where they belong, and the structure is already done.
A quick tip from me: keep a running “facts file” for each client or project with prices, dates, metrics and names. When the [ADD] markers show up, filling them takes minutes.
The formula behind all 20
Every prompt in the set follows one structure:
Role + Task + Audience + Goal + Tone + Length + Limits.
- Role: Who the AI should act as, like a senior editor or a skeptical investor.
- Task: The exact job, such as outline, rewrite, compare or proofread.
- Audience: Who will read the final doc.
- Goal: What the doc needs to achieve, like getting a yes, a meeting or a signature.
- Tone: Formal, friendly, direct or warm.
- Length: A word count or page limit.
- Limits: What the AI must not do, like inventing numbers or changing your style.
Here’s a quick example built on that formula: “Act as a senior proposal editor. Tighten this proposal for a CFO at a mid-size logistics company. The goal is to secure a discovery call. Keep the tone confident and plain. Stay under 600 words. Don’t invent any figures, and mark missing facts with [ADD].” That’s seven building blocks in one short prompt, and the output is far more useful than “make this better.”
The “Limits” piece is the one most people skip. It’s also what stops AI from drifting into generic filler.
The founders moving fastest aren’t writing more. They’re rewriting less.
That closing line from the creator sums it up. The win here isn’t more output. It’s fewer late-night redos. Know a founder buried in proposals right now? Pass this along. And think about which document you’d hand to AI first.
All 20 prompts are laid out in the infographic attached to the original post, so check out the full LinkedIn post to grab the complete set.