How to Start Conversations on LinkedIn Without Sounding Stiff or Salesy

How to Start Conversations on LinkedIn Without Sounding Stiff or Salesy

Publication Date
September 12, 2025
Summary

LinkedIn is still a social platform — just one where people wear nicer shirts. If you want replies (and conversations that lead to paid work), you don’t need to be more formal. You need to be more you.

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The Meltzer Seltzer Team

You know that sinking feeling when you reread a message you sent on LinkedIn and think, “Oh no… did I actually write that?”

We’ve all been there — trying so hard to sound professional that we accidentally become stiff, formal, or robotic.

And the result? Crickets.

The truth is: most follow-ups flop not because you’re annoying, but because you’re not sounding like a human. LinkedIn is still a social platform — just one where people wear nicer shirts.

If you want replies (and conversations that lead to paid work), you don’t need to be more formal.

You need to be more you.

The Truth About Follow-Ups (and Why So Many Messages Flop)

We’ve all seen messages like this:

“Hello, [Name], I hope you’re doing well. I noticed you work at [Company]. Would you possibly have need for my services? Thank you kindly. Warmly, [Your Name]”

Cringe, right?

It’s the LinkedIn version of walking up to someone at a party, handing them your resume, and walking away.

Here’s why this kind of message flops:

☠️ It’s stiff, formal, and not how real humans talk

🤷🏻‍♀️ There’s no hook — nothing that shows why they should care or reply

🤝 It makes networking feel transactional instead of like, y’know, connecting

Most freelancers assume professionalism = formality.

But what actually works is warmth, clarity, and low-pressure connection.

Try This Instead: A Follow-Up That Actually Works

Here’s a message that gets real replies:

“Hey [Name], thanks for connecting! I’m a [your service] freelancer for [who you help]. I saw you're [job title] at [company]! I love getting to know other [content folks / marketers / designers] in my niche.”

Short. Friendly. Low-pressure.

That’s what gets responses — and what starts real conversations that lead to paid work.

This message works because it:

  • Sounds like an actual person
  • Builds rapport instantly
  • Gives context without over-explaining
  • Keeps the door open for future outreach
  • Feels natural for both sides

LinkedIn is one of the easiest places to start new professional relationships — if you talk like a human.

Why Warm, Simple Messages Convert Better

Freelancers often worry about “bothering” people, so they compensate by being overly formal or vague.

But here’s what potential clients actually want:

  • A clear sense of who you are
  • A quick snapshot of what you do
  • A message that respects their time
  • An energy that feels approachable, not salesy

Your goal isn’t to pitch in message one.

Your goal is to connect — and set the stage for future follow-ups.

Because here’s the part most people forget:

Relationships convert. Not cold pitches.

What This Means for Your Follow-Up Strategy

A strong follow-up flow is:

  • Human
  • Direct (but gentle)
  • Consistent
  • Low-pressure
  • Timed well

You don’t need complicated sequences or heavy sales tactics.

You just need to sound like yourself — and actually stay in touch.

This might look like:

  1. Intro message (human, no pitch)
  2. Light follow-up 2–3 weeks later
  3. Helpful check-in another 2–3 weeks later
  4. Quarterly touchpoints that keep you top of mind

Each one can be short, warm, and simple.

People are much more likely to respond to something that feels like it came from a real person, not ChatGPT circa 2017.

FAQ: Follow-Ups on LinkedIn

How soon should I follow up after someone accepts my connection request?

Send your intro message right away — the conversation window is warmest in the first 24–48 hours.

Is it okay to follow up more than once?

Yes. Most people are busy, not uninterested. Following up 2–5 times (spread out) is standard and effective.

What if I feel annoying?

Feeling annoying is emotional; being annoying is tactical. As long as you’re spaced out, friendly, and not pitching aggressively, you’re fine.

Do I need a script for every outreach message?

No — simple, repeatable templates work best. Your intro should be personal, not perfect.

What if they still don’t reply after multiple follow-ups?

Move them to quarterly check-ins. Timing changes everything, and many clients say yes months after the first contact.

Why does my formal message get no replies?

Because formality feels cold. People respond to warmth and clarity — not stiff business speak.

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