How to Use ChatGPT to Personalize LinkedIn Outreach at Scale (includes prompts)

A lot of people have asked me how to use tools like ChatGPT to boost their LinkedIn outreach.

And at first, I was very skeptical.

There's a lot of human touch that goes into good outreach.

And every message I've seen ChatGPT write... has sounded just like the rest of the garbage that fills most peoples' LinkedIn inboxes.

But eventually I realized that ChatGPT can be trained to mimic a real person.

And with a bit of playing around, I've developed a personalization strategy that I actually use with my own account, and for certain clients.

But in order to effectively use ChatGPT for outreach, you first need to know how it fits into a successful outreach strategy.

What to use ChatGPT for

The first thing to know about AI is that it learns from what's already out there.

And since 95% of LinkedIn outreach is absolute garbage...

You don't want AI creating your strategy for you.

It will just mimic what it sees.

However, while AI isn't great at creating outreach strategies, it can be effective at implementing them.

If you have a framework that has been tested & proven to work,

ChatGPT can help "fill it out".

Two of the greatest strengths of ChatGPT are research & idea generation, and in this article I'm going to show you how to leverage both

To implement a strategy that already works without ChatGPT...

But more quickly & efficiently with it.

Let's dive in.

The Strategy

This strategy consists of 4 specific segments.

It's one of the simpler LinkedIn outreach strategies, which makes it perfect for coupling with ChatGPT.

As I mentioned, ChatGPT thinks in frameworks, so if you give it a cue like "fill out these 4 segments in order", you're already setting it up for success.

Here is the framework:

1. Custom first line
2. Reason for reaching out
3. Your offer + case study
4. Qualifying question

I'm going to walk you through each step individually, and by the end we'll have a chat programmed to write personalized outreach messages...

To any profile on LinkedIn...

In 60 seconds each (we tested it).

Step 1: Draft the Body

The body of this message can be used over and over again.

As long as your list is specific enough, the body of the message will apply to everyone on the list.

Then you can add in a personalized first line, and the whole message will feel like it was written specifically for that person.

I call this strategy bulk personalization.

Because it balances personalization & scalability.

And using ChatGPT makes it even more scalable.

So let's write the body first.

Your Offer + Case Study

This is the "meat & potatoes" of the message, so it's where we'll start.

Here's the prompt:

ChatGPT now has the formula for this section, and will ask us a series of questions to personalize it to our offer:

Answer those questions specifically, giving ChatGPT as much information as you can.

In my experience, more info is better because ChatGPT can distill it into fundamental principles... but it can't guess if you don't tell it.

Two pointers here:

1. Make sure your target market is specific. Like I mentioned earlier, "SaaS startups in their first 3 years" is better than "business owners". If you have multiple niches, write a different body for each niche.
2. Make sure the case study comes from a client within that specific niche. If it's a bit off, just frame their industry to sound more relevant (for ex. if your TM is "SaaS startups" but your case study is a web development agency, you could say "a tech business").

Here are my answers:

ChatGPT will now give you a draft of the offer + case study it wrote for you:

If you don't like it, you can either ask ChatGPT to rewrite it, or you can rewrite it yourself.

Remember, like I said at the beginning:

One of ChatGPT's top 2 skills is idea generation.

It may not write the perfect case study in your voice, but it will definitely get your wheels turning and then you can polish it off.

Here was my edit:

Now, on to the next one.

Qualifying Question

If the offer + case study is the meat & potatoes...

The qualifying question is dessert ("Do you want to order more?")

This is where you ask if your offer is relevant to the prospect.

It's important in this segment not to sound persuasive (like you want them to answer affirmatively)...

You're just qualifying them to see if it's even relevant.

Here's the prompt:

ChatGPT sends back 10 possible questions:

Now, just pick one (or edit it), and add the following text to the end of it:

"Just let me know - happy to share some ideas if so."

Again, you can edit all of this to be more aligned with your style. No need to stick to the exact wording here.

Send ChatGPT your qualifying question along with the additional sentence, and add it to the overall message:

Reason for reaching out

Ok, so if the offer + case study is the meat & potatoes...

And the qualifying question is dessert...

The reason for reaching out is the appetizer.

It's how you introduce the idea that you may be able to help them with something, and transition from the personalized first line (welcome to the table) into the offer.

When written correctly, it will sound like you're just curious whether you can help them or not..

Not like you are personally attached to what they say.

That's why this prompt reiterates to ChatGPT not to convince but more so to qualify.

Here's the prompt:

ChatGPT proposes these 10 lines:

I liked #4 a lot so I tweaked it a bit and asked ChatGPT to add it to the message:

Now ChatGPT sends back the overall message:

Because I'm a perfectionist, I make some final tweaks:

And ChatGPT sends back this beautiful body ??

Alright, so it's a good message... not great...

While it's a little different in tonality than the norm (more respectful and open-minded in my opinion), it's not too far off.

Let's take it to the next level.

Step 2: Writing the Personalized First Line

To write the personalized first lines, we're going to open a new chat.

That way, we'll have one chat with the message body saved...

And one that will add personalized first lines for each prospect.

So, with the new chat opened, we introduce our longest prompt of the day:

But wait, there's more:

This prompt is a doozy, but it's because this segment is the most personalized one.

It has to sound genuine, so we need to teach a robot not just to sound like a person...

But to sound like a cool one that people want to connect with.

Should be easy enough ??♂?

Chat GPT will first demonstrate that it understands the task:

Now we just need to share the LinkedIn profile.

There are 2 ways we COULD do this:

1. Share the profile link.
2. Find another way because 1 doesn't work ??

It would be lovely to just upload a profile link...

But LinkedIn is a closed platform, which means ChatGPT can't access profiles without logging in.

And, for better or for worse, no one has made ChatGPT a LinkedIn profile just yet....

So we have to find another way.

The strategy I discovered has worked very effectively though, and it doesn't take too much extra effort.

All you have to do is go to the profile, click the "More" button in the bottom right of the header, then click "Save to PDF":

This will save the profile as a PDF, with all the sections of their profile saved in a resume-like format:

You're not going to open the PDF, it's just a format that ChatGPT can read and use for its research.

In order to upload the PDF, you'll just click this paper clip icon in the left-hand side of the chat box:

Then select the file you just downloaded (it will be named "Profile (x).pdf", where x is a number that increases every time you download a new profile).

You will see the file upload to ChatGPT, then once it turns from a spinning wheel into this file icon, you'll be able to press send.

Since ChatGPT already knows what to do, you won't have to add a prompt at all. Just click the send arrow to the right.

ChatGPT will now read the document (in like 5 seconds):

And send back a few ideas:

Now these are not world class first lines...

But like I said, ChatGPT is best at (1) research, and (2) ideation.

So while you'll still need to tweak the first lines a bit, within 20 seconds you have 5 ideas of things to comment on without having to look through the profile yourself.

(We tested it with my team:

• Our average time to read a profile & write a custom first line was 5 minutes.
• ChatGPT writes 5 in 20 seconds.)

So take a few seconds to review & edit the ideas.

Then jump into the other bot (which has the message body saved), and ask it to add the custom first line:

Here is the first line I chose for Victor, which was a combination of 2 of ChatGPT's ideas:

All you gotta do it send it.

ChatGPT responds:

And we have our final message!

I then tried this with 2 other "prospects" - here are their final messages:

Not too shabby!

So, for any of you who'd like to use these prompts and experiment with adding ChatGPT into your LinkedIn outreach strategy,

I've added the message templates to a Google Doc:

ChatGPT Personalized Outreach Prompts

Happy outreaching!