Every freelance coach tells you that you can find clients on LinkedIn by sending DMs or “building a relationship” with your ideal client.
I agree.
But most of the time, your ideal clients do not appreciate receiving unsolicited messages.
So, how do you send a message to a stranger asking for work without annoying them?
There’s no surefire way to do so, but I can show you the LinkedIn messages I’ve sent—messages that have helped me generate leads and sign clients.
The point is to show you that it is possible and also help you model your outreach messages so you can get responses.
Sending cold connection requests
There are two types of LinkedIn users: those who add notes to their connection requests and those who don’t.
I’m both, lol.
Because I pay for LinkedIn, I can send unlimited notes with my connection requests. And while I’ve had success connecting with my ICPs without using notes, it often felt weird to start a conversation with them afterward.
So I started experimenting with adding a note in the connection request.
My reasoning? They would see the note (which explains why I’d like to connect) and then decide whether to accept or not.
What I’ve found from my lil experiment is that my ICPs accept these requests with notes at the same rate as the ones without.
But I like these requests with notes better because it already sets the tone for the conversation.
Here’s an example:

I started the note with a genuine compliment, then introduced myself and explained why I wanted to connect.
The recipient replied and said they were happy to work with writers.
The template:
“Hi [Name], [Compliment. It could be something about their profile or the content they create.]
[Introduce yourself and say why you’re connecting.]”
Sending a warm LinkedIn DM
You likely already have potential clients who have connected with you and often interact with your content.
It doesn’t hurt to ask if they work with writers.
Here’s an example of a message I sent:

The template:
“Hi [Name],
[Compliment. It could be something about their profile or the content they create].
[State why you’re reaching out]
[Include some social proof.]”
Sending a cold LinkedIn DM
I had recently connected with this person and noticed they produced a ton of content on their company website.
But the problem was that we had barely interacted on the feed or anywhere else, for that matter.
I could have gone with insincere pleasantries. But most content leaders can see right through it.
So, like with the other DMs I’ve shared, I went straight to the point.
The first line was a compliment—something I put together from looking at their content for more than 2 seconds—and then my ask.
My goal was to get them to say yes or no before sending a complete pitch.

Fortunately, they said yes.
Sending another cold LinkedIn DM that led to work
This DM is similar to the earlier cold DM, but in this case, it led to paid work. I used the same approach, asking one question about whether they work with freelancers.

The reason I like this approach is that you get a yes-or-no response. If they say yes, you’ll know what the next steps for working with the prospect look like. And if their answer is no, you can spend your outreach resources elsewhere.
Sending a follow-up DM that led to work
The thing about LinkedIn DMs is that it’s messy, and most content leads get a ton of messages daily.
That’s why I recommend sending one or two follow-ups before calling it a day.
I had initially sent a cold DM to this prospect, but they didn’t respond. With Q4 around the corner, I figured it’d be a good time to reach out again, since many teams often reevaluate their strategy then.
So I sent this follow-up message:

It goes straight to the point and revolves around what the company might need at the time.
Reasons why these messages worked
1. I personalized the first line
Generic openers typically get ignored. I mentioned something specific, which proves I looked at their profile instead of blasting the same message to everyone. It takes 60 extra seconds, but it’s the difference between getting deleted and getting a reply.
Name-dropping clients like HubSpot was proof that I’ve done this before. If you don’t have big names yet, use results: “helped rank #1 for [keyword]” or “wrote content that generated 200+ leads.”
3. I made my intentions clear
I asked directly: “Do you work with freelance writers?”
Being upfront shows respect for their time and gets you an answer faster. Nobody likes trying to figure out why you’re in their DMs. Make it obvious what you want from the first message.
4. I asked one question per message
One clear question makes it easy to reply. The simpler you make their response, the more likely they are to respond.
6. I followed up
Most people don’t respond to the first message because they’re busy, not because they’re not interested. I send one follow-up after a week or two, usually around something timely, say a new quarter, funding news, or product launch. But don’t overdo the follow-ups.
7. I sent it to the right person
Don’t message the CEO of a 500-person company. Find the person closest to content decisions: content manager, marketing director, head of growth. Check who’s posting about content on LinkedIn.
8. I kept the messages short
I aim for under 100 words. One compliment, one reason I’m reaching out, one question. That’s the formula. If they’re interested, you’ll have plenty of time to share details later. Your first message’s only job is to get them to respond.
Your Turn
If you want to try this:
Make a list of 10 companies you’d actually want to work with
Find the right person on LinkedIn (content manager, marketing lead, etc.)
Look at their recent posts or their company’s blog
Send a message that shows you spent more than 30 seconds looking at their stuff
Keep it under 300 characters
Follow up once or twice if you don’t hear back (Time it around news about the company, e.g., recent funding or hiring, or around new quarters: Q1, Q2, etc.)
Got questions? Hit reply. I’d love to know if this approach works for you.
See you next week.
