There’s a special kind of dread that comes with a blank Word document at 11pm. You know the proposal is due tomorrow. You know what you want to say. But the cursor just keeps blinking. I’ve been there more times than I’d like to admit, so this post stopped me mid-scroll.
A LinkedIn creator just shared a really practical breakdown of how founders can stop writing every important document twice. The author’s point is simple. Most of us write proposals, investor updates, hiring plans and policies once in a rush, then again late at night when it actually matters. And when people bring AI into Word, they often make it worse.
The problem with lazy prompts
The pattern the original poster describes will probably sound familiar. You type one lazy line into the AI. You get back generic, robotic copy. Then you spend an hour making it sound human again. So you didn’t save any time at all. You just moved the work around.
The author admits to doing exactly that. Before, a proposal took them most of a day. Now it takes a focused hour, and the result reads better. Same tools, same Word document. The tool didn’t change. The approach did.
The big shift: treat AI like a sharp editor, not a ghostwriter. You stay the author. It handles the outline, the tightening and the checking.
I love this framing because it fixes the biggest complaint people have about AI writing. When AI is the ghostwriter, you get bland text that sounds like nobody. When it’s the editor, your voice and your facts stay in charge.
Where these prompts work
The expert built a set of 20 prompts around this idea. They work with Copilot in Word, Claude for Microsoft 365 and ChatGPT for Word. So whichever assistant your team already uses, you can put these to work today. Here are the 10 the creator recommends starting with, plus a bit on why each one matters.
The 10 prompts to start with
- Plan and draft: Ask for a full outline with word counts before you write a single line. This kills the blank page problem right away, because you now have a map with each section sized to fit.
- Mark the gaps: The AI puts [ADD] wherever your own facts belong. No made-up numbers. This is huge for proposals and investor updates, where one invented stat can wreck your credibility.
- Rewrite and improve: Shorter sentences, active voice, same meaning. Think of it as a quick tightening pass that keeps your ideas exactly as they are.
- Change the tone: You get two versions, one light touch and one full rewrite. Having both side by side lets you choose how far to go, instead of accepting whatever the AI decides.
- Cut it down: Hit your word count without losing the call to action. Anyone who’s trimmed a grant application or a one-pager knows how easy it is to accidentally delete the most important line.
- Proofread: Every error listed in a table, without touching your style. You see each fix and decide for yourself, rather than having your writing quietly rewritten.
- Get honest feedback: A 1 to 10 score from a tough but fair reader. This is a great way to stress-test a pitch before a real investor or client reads it.
- Format it: Headings, tables and a table of contents in one pass. That’s the tedious formatting work most of us put off until the very end.
- Extract actions: Every owner, deadline and decision pulled into one table. Perfect for meeting notes or long planning docs where tasks get buried in paragraphs.
- Repurpose it: Turn the doc into an email, an FAQ or a one-page brief. One solid document becomes several pieces of content without starting over.
The underrated one: prompt 16
This is the one that got me. The author calls prompt 16 the underrated pick, and I think they’re right. You give the AI two versions of a contract or proposal. It lists every change in meaning. Then it flags anything that could create a legal, financial or reputational risk.
The original poster says it’s the one they’d want before signing anything. Picture a client sending back a “slightly revised” agreement. Instead of reading both versions line by line and hoping you catch everything, you get a clear list of what actually changed and what might hurt you. That said, it doesn’t replace a lawyer on high-stakes deals. It just makes sure you walk into that conversation knowing what to ask.
Where to start tomorrow
The expert’s advice is refreshingly specific. 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 gets when nothing is made up.
Here’s how I’d put that into practice:
- Paste your rough outline and any bullet notes into your Word document.
- Ask the AI to draft each section and insert [ADD] wherever a real number, name or fact is needed.
- Go through the draft and fill every [ADD] with your own verified details.
- Run the rewrite or proofread prompt as a final polish.
The beauty of this workflow is that you never have to fact-check the AI’s imagination. It simply can’t invent things when it’s been told to leave a placeholder instead.
The formula behind all 20
Every prompt in the set follows the same structure, and it’s worth memorizing:
Role + Task + Audience + Goal + Tone + Length + Limits
Here’s a quick example of how that might look for an investor update: “Act as a startup communications editor. Tighten this monthly update for our seed investors so they understand our progress and next milestone. Keep it confident but not hype-y, under 400 words, and don’t change any numbers.” Every part of the formula is there, and it’s a world away from “make this better.”
Once you start writing prompts this way, you’ll notice the output needs far less fixing. That’s really the whole point.
The founders moving fastest aren’t writing more. They’re rewriting less.
That closing line from the author sums it up perfectly. The goal isn’t to churn out more documents. It’s to get the important ones right the first time.
The full set of 20 prompts is laid out in the infographic on the original post, so go check it out and save it for your next proposal. And if you know a founder buried in documents right now, pass it along. Which document would you hand to AI first?