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How to Craft LinkedIn Messages That Attract More Quality Leads for Your Business

Spring and nostalgia often go hand-in-hand in my little bubble. Right now, I'm thinking about how I got my very first project as a freelance writer.

It all started with an email challenge by Rachel Pedersen.

The Mission: Land your first/next $100 (or maybe it was $1,000) freelancing client in 10 days.

I followed Rachel’s daily instructions closely which involved

  1. Sending 10 to 20 connection requests to people who fit my target market.

  2. Messaging every person who accepted a connection request.

  3. Repeating steps one and two EVERY DAY.

My messages went something like this:

Hi [Person's Name],

Your page has so much energy [or some other genuine compliment].

Thank you for connecting with me, by the way!

What kinds of projects are you currently working on?

Right now, I'm building a ghostwriting business and I'm really excited about it. I think the world needs [better quality content/more authors and books], don't you?



Shorter Version

Hi [Person's Name],

Thank you for connecting with me.

[What they do or their job title or a piece of content they posted that you found interesting] sounds [interesting, fascinating, cool, etc.].

What's it about?/I'm curious, tell me more.



Now, some of you may be cringing, especially if you've been on the other side of one of those salesy DMs. But I kid you not, it worked. One of the many many people I reached out to happened to be a burnt-out PR consultant who was looking for someone just like me. Upon accepting my connection request, HE messaged ME saying something like:

“Hey, I checked out your profile and you seem like a perfect fit for what I'm looking for. Could we jump on the phone to discuss more?”

That brief conversation led to my first four-figure project ghostwriting Tweets for one of his clients, a massive corporate brand. The gig paid R1,900 per month for 10 hours of work.

SIDE NOTE: Just typing that figure fills my heart with tremendous gratitude. An R1,900 account doesn't seem like much today, but in the Autumn of 2019, it felt like a million bucks. Plus, I had my first reference and a few portfolio pieces that I could point to with pride.

I also built amazing connections during that period including ones that have led to other opportunities, both short-term and long-term.

The moral of the story?

Conversation starters are key to getting your foot in the door. Start with something interesting, relevant, and relatable. And it doesn't hurt to be bold. Have faith in yourself and the idea that you may have something valuable to offer. You never know where it might take you.

Why Generating Leads on LinkedIn Through Direct Messages Works

The biggest lesson I learned during the 10-day challenge is the purpose behind a successful messaging system — and this applies to any marketing strategy you're seeking to build as well.

It's all about qualifying prospects. Not everyone is going to be a good fit, so your goal should be to find the right people for your offering. The first filter is the connection request. If you send out 100 messages and 20 respond favorably to your message, you have potential INTEREST. If one of those 20 responses turn into a sales call or a conversion, then you have a QUALIFIED LEAD.

That's the point of all the content, all the messages, email opt-ins, and calls: they are different methods of qualifying leads to get them closer and closer to making a purchase.

As Daniel Priestly put it in Key Person of Influence, you're taking them on a journey through your echo system. Some people will camp out at the first pitstop while others will trek with you all the way to the end and beyond.

The more frequently you put your brand out there and the more consistent you are with your messaging, the better position you'll be in to find qualified leads and be top of mind when they or someone they know needs your service.

Crafting Conversation-Starters that Resonate with Your Ideal Client

Now that I've shared my story about how I managed to land my first regular freelance gig from one single conversation starter, I'll share some tips for how you can craft yours.

First things first: do your research

View someone's profile and see what resonates with you. It could be anything from how their profile photo pops, the name of their company's brand, or a note on their current city.

For instance, it's freezing in Cape Town right now! If you stumbled upon someone's profile who hails from the city, you might start with something like, "Hey there, Person! Thank you for connecting. How are you surviving this chilly Cape Town winter? I hear it's the coldest one in a long time."

This is a great way to build a connection and put the person at ease. It's also an opportunity for you to reveal something about yourself.

If you don't feel like delving into the weather, try getting creative with your conversation starter. Pique their curiosity by referencing a book, movie, or show. Or tie in something from your current project or previous job experience that relates to what they do.

Second, use your elevator pitch.

Your elevator pitch is a powerful way to introduce yourself and your skills. An elevator pitch is simply a one-sentence statement that summarizes who you are and what you do.

For instance, "I'm a B2B content writer. I help consulting firms build brand awareness and generate leads on their LinkedIn Page."


"I'm building a [your industry] firm that specializes in [what you do] for [your specific niche]."

Make sure to keep it short and sweet, and don't be afraid to ask questions. This will allow you to get more information out of the person, and build a rapport.

Third, follow-up

As John Nemo says, "The magic is in the follow up." Connecting with someone on LinkedIn is only the first step. Once you've made contact, make sure to follow up with them.

You could send them a piece of content you think they might find interesting, or just reach out and see if they're available for a virtual cup of coffee. Either way, follow-up is key - it's the difference between a successful connection and one that fades away into oblivion.

Reaching Out on Behalf of Your Company/Employer

For those of you who work in sales or marketing, you might be reaching out to connect on behalf of a company or organization. When doing this, remember that you're representing the brand so you may want to use a slightly different elevator pitch the way you would at a networking event.

For example, "I'm a marketer at XYZ company. We help small businesses optimize their marketing campaigns and grow their customer base."


"I'm with ABC Company, a [your company's industry] agency in [your city]. We specialize in helping our clients [the problem you solve]."

You'll notice that the message goes beyond just stating the service your company provides.

By mentioning the problem you solve rather than the service, you are emphasizing the value your company provides and communicating WHO you serve and HOW you help them.

So, a month or two later when someone needs help growing their customer base, your company will come to mind due to the memorable elevator pitch you used (at least that's the theory behind all of it.).

Try the "Are You Interested In__________ Approach".

One last messaging script you can try is the Messaging Magic System by John Nemo. I haven't tried it out myself but I'm certainly intrigued!

It works like this: “Hi, Person. Are you interested in XYZ (the broad topic you provide/pain points)? The reason I'm asking is I have a great [some free resource you offer a guide/podcast episode/webinar/course/ etc.]. If you'd like to check it out, send me a thumbs up/Yes and I'll send it over. And if not, no worries, have a great day!”

This approach focuses on offering the recipient something valuable in exchange for their attention and email information. It's much more direct than the approaches I've tried in the past. It also gives you a reason to follow up if they permit you to send the freebie.

Know, Like, Trust

People buy from those they know, like, and trust. It's practically a law of business. Whether it's through content marketing, networking events, cold emails, or DMs, you've got to build relationships and connect with people.

Your goal is not to be pushy or sales-driven. Your goal is to build relationships and add value before you ask for anything in return. Remember, not everyone in your network will be a customer. Some will be collaborators, partners, or people who can help you achieve your goals. Your mission is to separate the potential customers from the rest.

Test it out. What do you have to lose?

Try out a few different messaging strategies and find which one works best for you. Test it with different audiences, or tweak the content of your message to make it more personalized.

Book a 1-on-1 Content Strategy Session with Robyn-Lee to get personalized advice on your content strategy. She'll help you create a customized plan for building relationships and connecting with people online.

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