#410: Stop Sending Crappy LinkedIn DMs (And Start Getting More Meetings)

Your "Let's Connect" messages are getting lost in the noise. Here's how to actually get responses and book meetings.

I woke up to another message in LinkedIn Message Notification:

“We're currently developing strategic partnerships with people like you. Our partnership program is designed to help expand your reach. Let’s connect so I can show you how to 10x your business.”

How many LinkedIn messages did you receive today from someone promising you they could build your business 10x? It is becoming comical for me. The coaching business seems to be the target industry for consultants to do whatever magic they claim and help us grow. The one I quote above in the intro inspired this blog!

If you’re in sales or marketing sending LinkedIn Direct Messages (DM’s) that vanish into the abyss unread, unanswered, or worse, ignored, you’re not alone. The platforms can be a goldmine for leads, with over 1 billion users and 63 million senior-level influencers as of 2025, but it’s also a graveyard for generic pitches. After 35 years in sales, I’ve had my share of flops from cold-calling using a desk phone, emailing, and LinkedIn DMs. I may have cracked the code on what works.

Spoiler Alert: It’s not about spamming InMail with “Hey, let’s connect!”

Here’s why your LinkedIn DMs aren’t converting and how to turn them into deal-closing machines.

The Problem: You’re Selling Too Soon

Picture this: You see that you have a mutual connection with a VP of Sales, and you slide into their DMs with, “Hi, I’m with XYZ Corp. Would you like to hop on a call about our CRM?” 

What’s the sound you hear? Crickets. Why? You’re treating LinkedIn like a cold-call script when it’s a social platform first.

In this case, start with what you both know!

“Hi, Jane. I see that we are both connected with Paul Langdon at StarShip.”

People don’t log in to buy; they’re there to network, learn, or flex their expertise. If they are there to learn, network, or show their knowledge, allow them to do that! Leading with a pitch screams desperation and kills the trust you are trying to build.

Fix It: Warm them up. For example, after you mention Paul from StarShip, you also notice that they post a lot of content; comment on their recent post,

“Loved your take on AI in sales, especially about pipeline efficiency.”

Build rapport over 2-3 messages before pitching. Data backs this up. HubSpot says 65% of B2B buyers engage after multiple touch points, not one-offs. To finish off this DM example, ask them a direct question that they could respond to from their content.

“I see that you mentioned XYZ tool in your post, what other tools did you look at, I’m interested in gaining knowledge there.”

The Problem: Your Messages Are Generic

“Hi, I’d love to connect and explore synergies.” Sound familiar? It’s the LinkedIn equivalent of elevator music: forgettable and skippable. Generic DMs blend into the 50 others clogging their inbox weekly. If your message could fit any prospect, it’s not specific enough to compel a reply.

Fix It: Get personal, fast. Skim their profile for ammo. Look for recent posts, job changes, and shared connections and weave them in. “Congrats on the new role at XYZ. How’s the transition going?” Specificity shows you’ve done homework, not just copied a template. 

Pro tip: Keep it under 100 words. LinkedIn’s stats show that short, tailored messages get 3x more responses.

Here is a hint for marketers trying to attract people like me: I post this article weekly on my LinkedIn site. It would be easy for them to use those articles and posts and make a simple comment. If they prove that they listened (or read) to me, I might respond to their messages when they promise a 10x business increase.

The Problem: You’re Not Solving Their Pain

Here I go again, customer discovery!

Most of their DMs focus on what they offer, not what I need. I’m so tired of hearing, “We’ve got the best analytics tool!” Great, but why should I care? If your message doesn’t scream, “I feel your pain,” it’s going to the garbage can. 

Fix It: Lead with their pain points. Research their industry; for example, for a sales director, try:

“Most sales leaders I talk to spend more time logging information into their CRM than selling. Do you have this trouble? If so, I’ve found a way to save as much as 10 hours a week.”

Name the problem, hint at the solution, and tease curiosity. No jargon, just relevance.

Bonus: Drop a stat or mini-case study that justifies and substantiates their problem.

The Problem: No Clear Next Step

Even if they’re intrigued by your hook, a vague “Let me know your thoughts” will flop. People are busy, and VPs aren’t sitting around pondering how to answer your message. Without a nudge, they’ll scroll past.

Fix It: End with a low-friction call to action. Try something like,

“I am researching this topic, and I would love your opinion on those tools. Would you have 5-10 minutes to answer a few questions? If so, here’s a link to a quick survey.”

You address their need to feel like experts and provide a non-threatening way to interact.

Wrap-Up

Your LinkedIn DMs are likely not converting because they are cold, generic, or fail to address pain points. Focus on why your prospects are on LinkedIn: networking, learning, or building their brand as experts.

Change your approach by offering value, personalizing extensively, addressing their issues, and gently encouraging them to take action. If you’re having problems converting these messages to meetings, let’s talk. You can find time on my calendar at this link:

SCHEDULE

Here’s a chance to comment:

What’s your go-to DM line?