How to Write LinkedIn Messages with AI (Without Sounding Like a Bot)

AI writes good LinkedIn messages when you give it a real reason to reach out and strict rules for each message type. Ask for "a LinkedIn message to a VP of Sales" and you get the average one: a pitch dressed up as a compliment.

Why LinkedIn is not email

A LinkedIn message arrives next to your name, photo and profile, often on a phone. Three things follow.

1. The relationship comes first. You usually connect before you message. Pitching in that first step skips the handshake.
2. Space is tight. Connection notes have a hard limit, and anything longer than a phone screen looks like a template.
3. Your profile is part of the message. A buyer who likes your note clicks your profile next. An honest headline does more than a clever note.

For email, read How to Write Cold Emails with AI. This page covers LinkedIn.

The five LinkedIn messages

Tell AI which message you're writing and its one job, or it will try to do them all at once.

These lengths are our course guidance, not LinkedIn's rules. LinkedIn sets its own caps, which have changed over time and can differ by account type, so check its current help pages.

Set up your LinkedIn rules once

Add a short LinkedIn section to your seller context file, in the instructions of your company approved AI assistant, so every draft starts with the right limits. No file yet? How to Build a Seller Context File has the template.

# LinkedIn rules
- I write every LinkedIn message myself with your help and send it by hand. Never suggest automation.
- Connection notes: under 300 characters, no pitch, no links, no meeting ask. One real business reason to connect.
- First message after connecting: 2 to 4 short sentences, one question, no product pitch.
- Comments: a point of view or a question about the post itself. Never mention my company.
- Follow ups: under 60 words, each with a new reason to reply.
- Never use: "I came across your profile," "I'd love to pick your brain," "Great to connect!," "Hope you're well," "quick question," exclamation points.
- Never imply we've met, talked or share a contact unless I tell you we have.
- Use only facts I give you about the person or company. If a fact is missing, ask me.

Write any LinkedIn message in 6 steps

1. Find a real reason

   Start from a verified trigger, such as a hiring push or a new leader. How to Use AI for Account Research shows how.

2. Check the person yourself

   Open their profile and confirm the role. AI's guess about a title can be out of date.

3. Pick the message type

   Not connected yet? Connection note. Just accepted? First message. Posted something relevant? Comment.

4. Draft with the matching prompt

   below, in a chat that has your LinkedIn rules loaded.

5. Run the 60 second edit

   Verify every fact, delete any warm up, read it aloud and make the ask one small question. Count a connection note's characters yourself; AI miscounts.

6. Send it by hand and log it

   Paste it into LinkedIn yourself, then note the touch in your CRM so your sequence stays in order.

Connection notes

A good note answers one question: why does this person want to connect with me? The answer is about their work, not your quota. With no real reason, send the request without a note rather than invent one.

Write 3 LinkedIn connection notes to {name}, {title} at {company}.

What I know (verified): {trigger, with where you saw it}. My role: {your role, one line}.

Rules: under 300 characters each, including spaces. No pitch, no product name, no link, no meeting ask. One business reason to connect that ties to their work. Plain words, no exclamation points.

Versions: one that mentions the trigger, one that mentions a shared interest in the problem, one that is a single sentence.

First messages after connecting

An accepted request means "sure, connect," not "pitch me." Make your first message about them and easy to answer in one line.

{name}, {title} at {company}, just accepted my connection request. My note said: "{paste your note}".

Write 2 versions of a first LinkedIn message. Rules: 2 to 4 short sentences. Thank them once, briefly. Ask one question about {the trigger or problem} that a {title} could answer in a single line. No product pitch, no meeting ask, no link. Don't repeat my connection note.

Then tell me which version you'd reply to as {name}, and why.

Comments that add value

Commenting on a buyer's post is the Day 8 LinkedIn touch in the course's sample sequence. It's public, so it shows your thinking to the buyer and their network. "Great post!" shows nothing. Use AI to find your angle, then write the final words yourself.

{name}, {title} at {company}, posted about {summarize the post in your own words, 2 or 3 sentences}.

Give me 3 angles for a comment that adds value: one from my experience with {your relevant experience}, one useful question about the post itself, and one respectful counterpoint or nuance. For each, write a 2 sentence starter I will rewrite in my own words.

Rules: never mention my company or product. No praise words like "great," "love this" or "spot on." No questions that are really a pitch.

Follow ups

On LinkedIn, one follow up with new value is usually enough. After that, let other channels in your sequence carry the conversation, or stop. "Just bumping this up" says you have nothing new.

Good angles: an approved peer example, an industry insight, a different pain the same role owns, or something they posted since. In a sequence tool, keep LinkedIn steps as manual tasks. For the email side of the same sequence, see How to Write Follow Up Emails with AI That Add Value.

I messaged {name}, {title} at {company}, on LinkedIn on {date} and got no reply. My message is below.

Write one follow up under 60 words that uses a new angle: {pick one: a peer example from my approved list / an insight about {topic} / a different pain a {title} usually has}. Don't say "following up," "bumping" or "circling back." Don't make them feel guilty for not replying. End with one easy question or no question at all.

<my_last_message>
{paste}
</my_last_message>

InMail style messages

Sometimes you can't connect first: the buyer ignores requests from strangers, or timing matters. LinkedIn's paid plans include ways to message people outside your network, often called InMail. Which plans include it, how many you get and the length limits all change, so check LinkedIn's current documentation. If you prospect in Sales Navigator, How to Use AI with LinkedIn Sales Navigator covers the research side.

Treat an InMail as a short cold email: a subject line, a reason, one line of proof and one ask. Use the Trigger, Problem, Proof, Ask framework from the cold email guide, cut harder.

Goal: get a reply from {name}, {title} at {company}, who I'm not connected to.

Inputs (verified): {trigger, with source}. Proof I'm approved to use: {one proof point}.

Rules: framework is trigger, problem, proof, ask. Under 100 words. A subject line under 6 words that names their situation, not our product. Open with their situation. One question they can answer in a few words. No "I came across your profile." Use only the facts above.

Format: 3 subject lines, then 2 versions: one direct, one curious.

Worked example: Calder Freight Systems

What never to do

Frequently asked questions