How to Turn LinkedIn Connections Into Paying Clients

Quick recap from the last 3 blog posts:

• We've covered tracking (week 1)
• Hot Prospects (week 2),
• Warm Prospects (week 3).

This week, we're tackling Cold Prospects.

These are people in your network who've gone cold. Old connections you haven't spoken to in 6+ months. LinkedIn connections from networking events. Fellow freelancers who do something complementary. Anyone with "marketing" in their bio who you're already connected with.

Most freelancers ignore these people completely because they assume "if it's been 6 months, it's too late."

Wrong.

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Your Network Is Bigger Than You Think

Here's what I realized last year: I had over 400 LinkedIn connections I'd never actually engaged with.

People I met at conferences. Fellow freelancers I connected with. Former coworkers from years ago. People who liked my posts but we never had a real conversation.

I started systematically reaching out to them. Not with a sales pitch. Just genuine reconnection.

Three of those conversations turned into clients within 60 days.

The truth is, most of your LinkedIn connections have no idea what you're currently working on. They might remember meeting you, but they don't know you're freelancing. They don't know what problems you solve. They don't know you're even available.

All you need to do is remind them.

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Why Cold Prospects Are Worth Your Time

Time passing doesn't kill relationships. It just puts them on pause.

Here's what makes Cold Prospects valuable:

You're not a stranger. You've already connected once. There's shared context, even if it's small. That puts you miles ahead of someone cold messaging them out of nowhere.

They might need you right now. Maybe their business has grown. Maybe they're dealing with a problem you can solve. Maybe their current freelancer isn't working out. You won't know unless you ask.

They can refer you. Even if they don't need your services, they might know someone who does. Freelancers especially love referring good people to their clients.

The key is reaching out with genuine value, not desperation.

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How to Reconnect With Cold Prospects

You're not asking for work. You're genuinely catching up and offering to help.

The message is simple: "Hey, it's been a while. Here's what I'm up to. What are you working on? How can I help?"

Here are three templates for different types of Cold Prospects.

Template 1: Fellow Freelancer / Complementary Service Provider

Use this for freelancers who do something related but not identical to what you do.

Subject: Been a minute, what are you working on?

Hey [Name],

It's been a while since we last connected (think it was [reference: that freelancer meetup/when we both commented on that LinkedIn thread/etc.]?).

I've been heads-down working with [your positioning: B2B SaaS companies on their paid acquisition/ecom brands scaling past $1M/etc.] and it's been going really well. Just wrapped a project where we [brief result that might interest them professionally].

Curious what you've been focused on lately? Still doing [their specialty]?

I'm always looking to connect with solid [their role: copywriters/SEO specialists/designers/etc.] for clients who need that expertise and happy to return the favor if you ever need [your specialty] help for your clients.

Would be good to catch up properly. Want to do a quick 30-min call sometime this week or next? No agenda, just a real check-in on what we're both working on and how we might be able to help each other out.

Let me know if you're down.

Best,
[Your name]

Why this works: You're leading with mutual benefit. You're showing them you have active clients who might need their services. And you're positioning the call as a genuine catch-up, not a pitch.

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Template 2: Former Coworker

Use this for people you used to work with at a company but haven't kept in touch with.

Subject: Overdue catch-up

Hi [Name],

Just realized it's been [timeframe] since we worked together at [Company], way too long.

I've been freelancing since [timeframe], working with [your positioning: mid-market companies on conversion optimization/DTC brands on their paid social/etc.]. It's been a good ride so far. Recently [brief interesting win/project that shows you're doing well].

What have you been up to? Still at [their last known company] or have you moved on?

I'd love to actually catch up and hear what you're working on these days. Want to hop on a quick 30-min call? My treat for the virtual coffee.

Also, if there's anything I can help with (client intros, freelance advice, connections in [industry], whatever), just say the word.

Let me know when works for you.

Best,
[Your name]

Why this works: You're acknowledging the time gap without being weird about it. You're showing you've been doing well. And you're offering help before asking for anything.

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Template 3: LinkedIn Connection from Networking Event

Use this for people you met once at an event and connected with on LinkedIn but never followed up.

Subject: Following up from [event name]

Hey [Name],

We connected on LinkedIn after [event name/context] back in [timeframe], and I've been meaning to reach out properly.

I saw you're working on [something from their LinkedIn: growing [Company]/building out paid acquisition for [Industry]/etc.], that's awesome. I've been doing similar work with [your positioning], and just finished a project with [type of company] where we [specific result].

Actually thought of you because [genuine connection: the challenge they faced is similar to what I saw on your profile/I saw your post about [topic] and it resonated/etc.].

Would love to grab a virtual coffee and hear more about what you're building. I'm also happy to share what's been working in [your area] lately if that's useful, no pitch, just comparing notes.

30 minutes this week or next?

Best,
[Your name]

Why this works: You're showing you've actually looked at their profile. You're connecting the dots between what they're doing and what you've been working on. And you're making it about them, not you.

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The Old Freelancer Way vs. The Modern Freelancer Way

The old freelancer:

• Assume if you haven't talked in 6+ months, the connection is dead
• Only reach out to people when you need something
• Send generic "let's catch up" messages with no context

The Modern Freelancer:

• Treat dormant connections as an untapped pipeline
• Reach out with genuine value and specific context
• Lead with how you can help them, not what you need

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Your Action Step

This week:

1. Open your LinkedIn and scroll through your connections. Find 5-10 people who fit the Cold Prospect category: fellow freelancers, former coworkers, or people from networking events you haven't talked to in 6+ months
2. Add them to your Sales Pipeline Tracker under "Cold Prospects"
3. Pick five people and send them a message using one of the three templates above
4. Track the outreach and set reminders to follow up if they don't respond in 5 days

That's it. Just five messages this week.

On the next post, we're wrapping up with Frozen Prospects. These are your dream clients who don't know you exist yet. Different ballgame, but incredibly effective when done right.

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