LinkedIn Messaging Strategies That Actually Get Replies

Most LinkedIn outreach fails because it’s too formal, too generic, or too sales-driven.

The truth is, LinkedIn DMs are not emails. If you’re sending stiff, overly professional messages that sound like they were copied from a cold email template, you’re losing opportunities before the conversation even starts.

Instead, think of LinkedIn messaging like texting or Instagram DMs—it should be casual, natural, and easy to reply to. The key to getting responses isn’t pushing a sales pitch, but rather starting a conversation and showing genuine curiosity.

Here’s how to craft messages that actually get replies.

1. The Icebreaker: Enter the Conversation with Genuine Curiosity

There’s no one-size-fits-all approach to sending LinkedIn connection requests. Some people prefer no message at all, while others appreciate a short, thoughtful introduction. What doesn’t work? Sales pitches disguised as introductions.

What I’ve seen work best:

✔ Let your profile do the heavy lifting—some people will connect without a message.

✔ If you do send one, make it curiosity-driven—mention a shared interest, mutual connection, or their recent post.

✔ Never pitch in the first message—LinkedIn is about relationships, not transactions.

If you do send a message, make sure it’s engaging, relevant, and curiosity-driven. The goal isn’t to pitch—it’s to start a conversation.

What Works:

✔ Mention a recent post or comment they made and ask for their take.

✔ Reference industry trends and ask how they’re seeing things play out.

✔ Keep it casual and conversational—like you would in real life.

Example Icebreaker Messages:

❌ What Not to Send:

"Hey [Name], I’d love to connect and share how my company helps businesses like yours scale with AI-driven automation solutions."

(Too salesy, too formal, and not engaging.)

✅ A Better Approach:

"Hey [Name], saw your post on [topic]—I really liked your perspective. I’ve been hearing mixed opinions on this. Curious—what do you think will happen next?"

"Hey [Name], I noticed we’re both in [industry]. I keep hearing people talk about [trend]. Would love to hear your take on it!"

Why this works: It’s easy to reply to, doesn’t feel forced, and sparks an actual conversation.

2. Lead With Value—But Not in a Transactional Way

A big mistake in LinkedIn outreach is treating “value” as just another way to sell. People don’t want random case studies or “helpful” PDFs shoved in their inboxes. Instead, they want real conversations that help them think differently.

The best way to provide value? Invite their perspective.

How to Do This:

✔ Ask about their biggest challenge without directly making it about your offer.

✔ Share a short insight or trend and ask if they’re seeing the same.

✔ Make them feel like an expert, not just a potential lead.

Example Value-Driven Messages:

❌ What Not to Send:

"Hey [Name], thanks for connecting! I’d love to book a call to discuss how we can help you increase revenue by 200%."

(This is about you, not them. They don’t care yet.)

✅ A Better Approach:

"Hey [Name], I’ve been having a lot of conversations about [industry challenge] lately. Some people say [opinion A], others say [opinion B]. Curious—what’s your take?"

"Hey [Name], I just read a report on [industry trend]—some really interesting insights. Are you seeing the same thing on your end?"

Why this works: It makes them feel like an insider, not just another target for a sales pitch.

3. Follow Up Without Being Annoying

Most people won’t reply to your first message. That’s just how it goes. But following up doesn’t mean sending another sales pitch—it means keeping the conversation natural.

Example Follow-Up Sequences:

Follow-Up #1 (3-5 Days Later) – Gentle Nudge

"Hey [Name], just following up on my last message—any thoughts on [topic]!"

Follow-Up #2 (Another 5-7 Days Later) – Referral Request

"Hey [Name], totally understand if this isn’t the right fit for you—would you recommend anyone on your team or in your network I should connect with?"

Follow-Up #3 (Final Soft Close – 1-2 Weeks Later) – Content & Open Door

"Hey [Name], I’m always sharing insights on [topic]. If you ever have any questions, feel free to reach out!"

Why This Works:

✅ Follow-Up #1 – Keeps it casual, no pressure.

✅ Follow-Up #2 – Gets straight to the point with a referral ask.

✅ Follow-Up #3 – Reminds them of your content while keeping the conversation open-ended.

This keeps your follow-ups short, clear, and natural, while still giving multiple ways for them to engage.

Key Takeaways for LinkedIn Messaging That Gets Replies

✔ Keep it casual – LinkedIn DMs aren’t formal emails. Talk like you would in a normal conversation.

✔ Start with curiosity – People love to share their opinions. Ask for their insights instead of pushing your own.

✔ Provide value without expecting something in return – Not every message needs to be a pitch. Some can just be about building relationships.

✔ Follow up in a low-pressure way – If someone is interested, they’ll engage. If not, don’t force it.

The best conversations on LinkedIn feel natural, not scripted.

Want to refine your LinkedIn messaging strategy? Send me a DM on LinkedIn—I’d love to chat.