How to Book More Meetings from LinkedIn DMs

TL;DR:

• Send a blank connection request to increase acceptance rates
• Engage with prospects' content and research their profile before sending a DM
• Follow up with triggers and engagement from prospects
• Transition to the ask by offering solutions to their challenges
• Build credibility on LinkedIn to increase response rates and drive warm conversations

You're probably using email and cold calls to book meetings. While those channels do work, using them with LinkedIn can help you get much better response rates.

Messages sent from LinkedIn are far less likely to end up in spam, and the reply rates are much higher — this is especially true if you build some credibility through posting to the platform often.

We do have a guide on LinkedIn DM templates (as well as comment templates) for sales, but here's how to book more meetings from LinkedIn DMs.

8 Steps to Booking More Meetings from LinkedIn DMs

Step 1: Send a Personalized or Blank Connection Request

When connecting with someone on LinkedIn, the approach depends on the context.

If you have a mutual connection or a valid reason to reach out — like you've talked to someone else on their team who suggested you connect — include a highly personalized note. Otherwise, it’s better to leave the connection request blank.

Reponse rates on highly-personalized connection notes have been reported to be as high as 70%. We've seen about 20% reply rate on blank requests.

You should never include a sales pitch in your connection request. This is an immediate decline.

You'll find that connection requests timed alongside other outbound sequences (like email) tend to see improved acceptance rates.

Step 2: Find a Reason To Reach Out

Before you put anyone into a list, you need a feasible reason to reach out to them. This is where you set up your sales triggers.

First-party engagement (when someone interacts with your content or a related topic) and triggers (events like job changes, announcements, or team growth) provide excellent reasons to reach out.

It also gives you insight into what their challenges might be.

You want to make an observation and ask a question.

Examples

1. When a prospect likes a post from you:

“Hey [Name], I saw that [topic] might have hit home for you. I recently worked with [client] to create a Playbook on this — thought you might find it helpful! Here’s the link.”

2. When you identify a relevant signal (job change, a website visit):

“Hi [Name], I noticed your team recently [specific initiative]. Curious — how are you approaching [related challenge]? Would love to hear your take!”

3. When you find a common challenge you can solve for:

“Hi [Name], I often hear from [roles] at companies like yours that [specific challenge] can be a sticking point. Is that something you’ve experienced? Would love to hear your thoughts.”

Step 3: Prep Before You DM

Good outreach begins before you send that first DM.

Engage With Their Content

Like, comment, and share their posts to build rapport. Thoughtful engagement shows genuine interest and warms up the conversation.

Do NOT programatically like their old posts and send a generic, automated message. Everyone does this. This is not authentic engagement whatsoever.

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You might:

1. Engage in deep-dive discussions, providing your expertise or perspective on something
2. Agree or disagree with a topic and expand on why (keeping it polite!)
3. Give feedback on a product or share a relevant experience
4. Share a helpful resource based on the topic

You'll also want to see what they've been posting lately to better contextualize your outreach.

Step 4: Transition to the Ask

Once you've built some rapport and have gotten replies, it's time to naturally transition to the ask.

The key here is to segue into your solution as a natural solve for what you've been talking about — you're helping them, not the other way around.

Remember to show empathy and understanding before you dive into the pitch.

Example DM Templates:

1. “Thanks for sharing your thoughts, [Name]! I have a few ideas about [specific challenge] that might help. Would you be open to a quick 15-minute call?”
2. “Maybe you could share more about how you’ve been tackling [problem]. I’d love to brainstorm with you — open to a quick chat?”

Go Multichannel

You want to go 'surround sound' with your prospect.

Mention to them that you've left them a voice mail or dropped them an email to reinforce your outreach.

Use Voice Notes and Personalized Videos

This was mentioned above, but consider sending personalized voice notes and video messages to help you stand out a bit more from the crowd.

"Hey [Prospect], I noticed your recent post about [topic]. I often speak with [similar roles] who face similar challenges, and we recently helped [client] achieve [specific result] by [solution]. Would you be open to learning more?"

Bonus: Build a Credible LinkedIn Presence

Your outreach is much more effective if prospects see you as a credible voice in your industry. Establishing a strong LinkedIn presence builds trust and increases response rates across the board, as seen by the following companies:

• DreamData has driven +$1M in pipeline for the team through social selling
• For RB2B, 75% of the folks who engage with their founder-led content are dead middle-funnel ICP
• Nick Bennett from TACK drove $2M in pipeline for his former company, Alice, through LinkedIn alone

Here's Isaiah Crossman, former CRO of Tropic (who went from first AE to CRO at $XX million run rate in 4 years) on the value of LinkedIn for sales.

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How to Build Credibility:

• Share consistent, value-driven posts about your expertise.
• Engage with others’ content to expand your reach.

And you can do this automatically with Letterdrop.

• Turn your sales calls into LinkedIn posts automatically (objections, questions, you name it)
• Boost your visibility through automatic like, comment, and repost requests from connected team or partner accounts

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Final Thoughts: Be Human

Don't just be another bot in an inbox. With just a little research on your part and a true-value first message, you could be booking far more meetings through LinkedIn DMs.

If you're looking to build your credibility on LinkedIn to drive more warm conversations, give us a shout.