Stop Feeling Awkward How to Start Conversations That Lead to Clients on LinkedIn

Let’s face it: nothing feels more uncomfortable than reaching out to someone you just connected with on LinkedIn and having no idea what to say.

You don’t want to come across as pushy. You don’t want to pitch out of the blue. You definitely don’t want to send a message that sounds like a bad AI-generated script.

I’ve been there. And I promise you, there’s a better way.

In Build Connections on LinkedIn with Confidence, I show you exactly how to start and nurture conversations that are genuine, easy, and lead to the kind of clients you want to work with.

The truth about messaging on LinkedIn

So many coaches and service providers hesitate to reach out on LinkedIn because they don’t want to be "that person."

You know the one:

• Cold DMs right after accepting a connection

• Copy-pasted sales pitches

• Overly formal language that doesn’t sound like a real human

But here's the thing: you can reach out in a way that feels natural. In fact, when you know what to say and how to say it, messaging becomes one of your most powerful tools for building trust.

Here's what I do instead

When I connect with someone new, I treat it like I would a real-life networking event.

I start light. I take a genuine interest. I comment on something in their profile or content. I make it about connection first.

Inside the course, I give you:

• DM swipe files that sound like you (not a sales robot)

• Message templates that create opportunities for real conversations

• A Market Research Post template that helps you learn directly from your audience

This isn’t about manipulating a connection into a call. It’s about starting a real conversation—and letting the next step come naturally.

Want to see it in action?

Here’s an example of how I might start a conversation:

“Hi Sarah, I came across your profile after reading your post about burnout in leadership roles. It really resonated—especially your point about boundaries. Would love to stay connected and keep learning from your content.”

Notice what’s missing? A pitch. This kind of message opens a door, not pushes through one.

Market Research That Starts Conversations

One of my favourite ways to connect with potential clients is to share a market research post that asks a question relevant to the service I offer. It’s a post written not to sell—but to listen.

When someone engages with it, it opens the door to a thoughtful follow-up message, like:

“Thanks for commenting on my post about [topic]. You gave me a new perspective—would love to hear more about how you're handling that in your work.”

This approach has sparked genuine conversations, built my network, and led to aligned client work.

3 Steps to Start a Great Conversation on LinkedIn

1. Check their profile. Find something you genuinely connect with.

2. Lead with curiosity. Ask a question or comment on their content.

3. Follow up naturally. If they engage, keep the conversation going—don’t force the pitch.

People buy from people they trust

We know this. We say this. But on LinkedIn, it’s easy to forget it.

Everything about Build Connections on LinkedIn with Confidence is designed to help you:

• Show up as yourself

• Communicate clearly

• Build trust through every step

And that trust? It’s what turns a simple DM into a discovery call. A call into a client. A client into a referrer.

It gets easier with practice (and a plan)

If you’re nervous about messaging now, that’s OK. It doesn’t mean you’re doing it wrong. It means you haven’t found a strategy that works for you yet.

Once you do? The dread goes away. You’ll know who to connect with, what to say, and how to follow up without it feeling weird.

That’s what we cover in the course. And it’s what makes it possible for you to start building a business you love on LinkedIn—one real conversation at a time.

Final Thought:

If reaching out on LinkedIn gives you a pit in your stomach, you’re not alone. But there is a way to make messaging feel good—and actually get results.

You can start those conversations with confidence. I’ll show you how.

www.elainewalshmcgrath.com/Build-Connections-LinkedIn-with-Confidence