From Connection Requests to Client Contracts

LinkedIn. It's the world's largest professional network, but you probably know that already. What you might need to realize, though, is how powerful it still is when it comes to generating new business, especially for freelancers, consultants, and service-based entrepreneurs.

Yes, the constant connection requests from strangers can be annoying, but here's the thing—outreach is baked into the platform's DNA. The very nature of LinkedIn encourages you to reach out to potential clients. The question is, how can you make it work for you?

In this newsletter, I'm sharing my process for LinkedIn outreach—a method that consistently brings new business to my agency. You'll learn how to connect with potential clients, nurture those connections, and eventually scale your outreach through automation and delegation. Let's dive in.

Step 1: Know Exactly Who You're Targeting

I may sound like a broken record, but I can't stress this enough because you'd be surprised how many people miss the mark. You have to know who your ideal client is. I've talked about this before: without a crystal-clear picture of your target client, you'll send connection requests into the void, or worse, you’ll come across as just another annoying person online.

The key to LinkedIn outreach is starting with a list of leads you can approach. The best place to find relevant LinkedIn profiles is through the Sales Navigator. It allows you to filter your search and zero in on decision-makers based on criteria like location, industry, job title, and more. Check our previous issue on how to set things up.

Once you have your list, it's time to make your move.

Step 2: Send That Connection Request

Now that you've identified your leads, your next step is to send a connection request. While you cannot directly message any stranger, you can always send a connection request, including a message.

Here's the key: always include a short, personalized message when you send the request. Keep it simple; don't overthink it. Greet them by their first name, briefly(!) introduce yourself, and offer a reason for connecting. Ideally, that reason should be relevant to both of you, like a shared interest or mutual goals.

For my agency, for example, I'll mention that I'm connecting to exchange ideas on digital transformation projects since that's what my ideal clients care about. Here's a template you can adapt:

A connection request message has a hard cap of 300 characters, so make sure your template leaves room for the different name lengths of the people you are contacting.

Many won't respond, and that's okay. People are just as busy as you are; most are uninterested or cannot reply. These are probably not your ideal clients. LinkedIn outreach is a numbers game. That applies to any form of cold outreach. It works, but the numbers may be disheartening.

We are looking for enough engagement at this stage to move forward.

Step 3: Follow up

So, they've accepted your connection request. Now what?

Many people will silently accept the request without engaging further. This is where you come in with a simple follow-up message. Shoot them a casual, low-pressure question to start a conversation sometime after they accept. Here's an easy one that works for me:

It's light, conversational, and easy to respond to. You're not asking for anything big—just starting a dialogue. Some will reply with something thoughtful, while others might offer just a thumbs up or a generic response. You're looking for engagement, so pay attention to their level of interest.

I’ve had some great answers here from various people who told stories about how their week did not go according to plan, and it is a great segue into a longer conversation.

If they don't respond after a couple of attempts, move on. But if they do engage, that's where the real conversation begins.

Step 4: Qualify the Lead

The goal here isn't to sell. It's to gauge whether they might be a good fit for what you offer. After exchanging a few messages, they'll often ask about you or check out your LinkedIn profile if interested.

An optimized profile is crucial here—we’ll cover this in more depth in a future issue.

If they see something on your profile that aligns with their needs, they'll ask you more about it or suggest jumping on a call. That's your cue to take the conversation offline and dive into their pain points. I usually offer a discovery call, the same as for my cold email outreach, so this is where both outreach channels converge.

You will win new clients when you are in front of the right people at just the right time with an offer that serves their needs. But since we cannot control that timing, you have to go for higher numbers so you still eventually end up with enough clients.

But even if they don’t become clients immediately, they may still become clients later. as their needs change. For example, your lead moves to another company, or a new project is started internally,

What we are shooting for is becoming a blip on their radar, ensuring that we are the first person they think about and reach out to when a need arises. This is playing the long game.

But the human brain tends to forget things, out of sight, out of mind. To stay front and center in their minds, you have to nurture them, which is a topic that I’ll dive into another time. (It includes keeping them close to you, sharing updates, and organizing exclusive events.)

Step 5: Scale Your Outreach

Now that you've got the process down let's talk about scale.

Outreach is time-consuming, which is why automation and delegation are essential. To grow your outreach efforts without burning yourself out, you'll want to set up systems to automate parts of the process—like sending connection requests or follow-up messages—and delegate tasks that require a human touch, like qualifying leads or holding initial calls.

Next week, I’ll show you how to set up a system that does exactly that.