From Cringe to Connection: The Do’s and Don’ts of LinkedIn DMs

May 22, 2025
LinkedIn, Personal Branding, Social Selling

“Send me a DM!” It sounds so casual. So friendly. So… easy.

But for most of us (myself included), DMs on LinkedIn are more like the wild west of cringe, copy-paste pitches and completely impersonal introductions. I can’t tell you how many times I’ve opened my inbox only to be greeted by a message that screams, “I didn’t even look at your profile, but BUY MY STUFF.”

That said…

My DMs? They’re also where most of my business comes from.

Yep. Most of my speaking gigs and training referrals originated in someone’s inbox. So while there’s a lot of noise and nonsense, there’s also gold—if you know how to use your DMs to build real relationships (not just blast sales messages like it’s 1999).

Here’s how to make the most of LinkedIn’s DM feature so you build trust, stay top of mind, and—eventually—take the conversation off-platform (where real biz gets done).

✅ DO: Treat Your DM Like a Bridge, Not a Billboard

DMs aren’t the place to “close” business. They’re where you start to warm up a connection.

Think of the DM as a springboard—its entire job is to gently transition the relationship from public-facing content to a more personal exchange. From there, if the timing is right, you can move the conversation into email, a phone call, or that glorious first Zoom coffee chat.

✅ DO: Use DMs to Deliver Value

If you’re popping into someone’s inbox, make it worth their click.

Here are a few ideas:

Send them a helpful article (ideally NOT your own… yet)
Congratulate them on a recent post, milestone, or talk
Share a quick audio or video message (these go a long way toward building trust)
Ask a thoughtful, specific question based on their content or work

Remember: it’s not about you. It’s about them.

✅ DO: Keep It Short and Sweet

LinkedIn’s DMs are like the texting of the professional world. They’re not where we go to read a novel.

Your message should:

Be brief
Get to the point
Be easy to respond to

If they want more info? That’s what your website, email, and Calendly link are for.

✅ DO: Add a Personal Touch

Sending your message from mobile? Bonus points! You can use:

Voice memos (great for letting your tone come through)
Quick videos (perfect for humanizing your outreach)
Emojis and light humor (when appropriate!)

These tiny personal touches can take your message from “just another DM” to “wow, that felt like a real human.”

❌ DON’T: Lead With the Pitch

This might sound harsh, but… no one logs onto LinkedIn hoping to get pitched.

LinkedIn is a networking platform, not a shopping cart. So skip the “let me tell you how I can help you grow your revenue 400%” intro.

Instead:

Start with connection
Lead with curiosity
Build trust

Then, move the conversation off-platform if there’s potential for partnership.

❌ DON’T: Be a DM Gnat

Follow-ups are fine. Five messages in a row without a response? Not fine.

LinkedIn’s messaging system is clunky, and things do get lost. But respect your prospect’s inbox. If you haven’t heard back, circle back once (max twice), then let it go. Otherwise, you risk becoming the reason their “block” button gets some use.

❌ DON’T: Brag. (Seriously.)

DMs are not your personal TED Talk stage.

If your message includes 3+ “I” statements in a row, it’s time for a rewrite. Instead of showing off how interesting you are, show your prospect how interested you are in them.

Ask about their work. Mention something from their content. Shine the spotlight their way.

Final Thought: DMs Done Right Can Change Your Business

Sure, most of my LinkedIn DMs go ignored. That’s just part of the game.

But the ones that land? The ones that actually build relationships and trust?

They’ve brought me speaking gigs, workshops, podcast invitations, and amazing clients.

If you want to stand out and use your DMs as a relationship-building powerhouse, not a digital sales flyer, then you’ve got to do it right.

Want to Get Better at LinkedIn DMs?

We talk all about smart DM strategies inside my LinkedIntensive workshop—how to craft compelling messages, move conversations off-platform, and use DMs to grow your brand without sounding like a robot.

Save your spot here: www.leannecalderwood.com/workshop

Let’s make your DMs feel less like a cold call… and more like a warm invitation.

Follow Leanne on LinkedIn

Follow Leanne on LinkedIn™