034: Selling on LinkedIn (Without Being Salesy)—Part 2: Your DM Strategy

Done right, LinkedIn DMs are the fastest way to turn cold connections into warm business conversations. Here’s how.

Today’s email is for you if you’re experiencing these problems:

• You hesitate to send DMs out of fear of coming across as spammy or pushy.

• You struggle to move LinkedIn conversations into real sales opportunities.

• You’re sending LinkedIn DMs, but all you hear back is… crickets.

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Review

This is the eighth installment of the 4-Farmland Matrix (4FM) series. In it, we unpack a simple four-part framework that helps you identify and capitalize on your most promising sales opportunities—whether they’re new prospects, current clients, or ones that got away.

So far, we’ve covered these topics:

The 4-Farmland Matrix: Overview

• 026: Packing Your Pipeline with Low-Hanging Fruit.

Farmland 1: New (Desirable fields yet to be acquired)

• 027: The Psychology of Prospecting Success.

• 028: The One-Sentence Elevator Pitch.

  • 031: Micro Lesson: How to Generate Your Elevator Pitch Using AI.

• 029: Moving Beyond ‘Hope-Based’ Prospecting.

• 032: The Systematic Networking Playbook.

• 033: Selling on LinkedIn (Without Being Salesy)—Part 1: Your Connections Strategy.

Preview

In a previous article, I introduced the four ‘components’ of Systematic Prospecting in your sales process:

1. Systematic Networking

2. Systematic Social Selling

3. Systematic Outreach.

4. Systematic Referrals.

In the last post, we began discussing the second component—Systematic Social Selling—with Selling on LinkedIn: Part 1: Your Connections Strategy. Today, we break down Part 2 in the “Selling On LinkedIn” series: Your DM Strategy.

Overview

The Direct Message (DM) on LinkedIn is the most underrated tool in B2B sales.

But remember that sending DMs does not mean spamming or “pitch slapping” your contacts.

It means increasing awareness, cultivating trust, and building relationships—where a percentage of which will emerge as clients.

Your ultimate goal with DMs is to move your Ideal Customer Profile (ICP) connections off of LinkedIn into 1:1 in-person or video meetings.

It’s in the 1:1s where the magic happens, where you can gain the insight (and trust) you need to uncover new sales opportunities.

So, what are the different types of DMs to include in your Systematic Social Selling toolbox?

Here are seven to get you started:

1. New Connections.

2. Thank You for Engagement.

3. Loved that Post.

4. Catching Up.

5. Company Page Follow (Founders/ Owners/ Page Administrators).

6. Direct Request.

7. Holidays/ Special Days

Let’s break down each one.

1. New Connections

Initial DM After Connection:

When someone accepts your connection request, send them a warm, no-pressure message within 24 hours.

1. Don’t pitch, send links, or ask for anything.

2. Instead, keep it simple, be grateful, and be 100% focused on connecting, not selling.

Example:

Hi Jim,

A quick note…Really appreciate you connecting with me here on LinkedIn.

I look forward to following you here—and learning from your content!

All the best,

Sean

Reply DM to Local ICP Connections:

How do you respond when they reply?

Now, it’s time for an ‘ask.’

For example, when your new connection:

• Replies to your DM

• Is in your local area

• Matches your ICP or is a potential Center of Influence (COI)…

Take the opportunity to suggest a 1:1. Keep the invitation casual and optional, like this:

Thank you, Ashley.

I see you’re also here in the Orlando area.

If you're ever open to it, I'm always up for connecting over Zoom sometime to learn more about your story and the work you’re doing.

Until then, I look forward to your posts.

All the best,

Sean

Note: I used to schedule in-person coffee meetings with local contacts for the initial meeting. But I’ve found that I can do three to four productive Zoom meetings for every Coffee Connect. Then, if we hit it off during that initial meeting and want to continue the conversation, that’s when I suggest we meet in person over coffee. 

Reply DM to Non-Local ICP Connections:

For new connections who reply but aren’t local, I remove the local reference:

Thanks, Jim.

If you're ever open to it, I'm always up for connecting over Zoom sometime to learn more about your story and the work you’re doing.

Until then, I look forward to your posts.

My best,

Sean

2. Thank You for Engagement

When someone consistently engages with your content or shows particular enthusiasm for a post, acknowledge their support. These quick messages help deepen connections and show you notice their interactions.

Examples:

Ex. 1:

Hi Kyle, wanted to thank you for your engagement and support on several of my recent posts. Really appreciate you 🙏

Ex. 2:

Hi Eryn, Thanks so much for engaging today. Hope to see you around more. Have a great day!

Reply DM:

If the connection:

• Replies to your DM

• Matches your ICP or is a potential Center of Influence (COI)…

Then try this template:

[Start with a personalized reference to their reply. Then…]

Let's catch up on Zoom sometime whenever it works for our schedules. Would love to learn more about your story and the work you’re doing.

Until then, I’ll look out for your posts 👊

My best,

Sean

Example:

Their Reply to My DM:

Of course! It resonates with me. Feelings are mutual for your engagement on my posts!

My response:

That's great, Thomas.

Keep sharing your journey on LI—awesome content.

And I imagine it's a great way to help document your learnings.

Let's catch up on Zoom sometime, whenever it works for our schedules. Would love to learn more about your story and the work you’re doing.

Until then, keep up the great work 👊

My best,

Sean

3. Loved that Post

When content truly stands out, follow up with a personal message to deepen the connection.

But don’t just say that you loved the post—share with them why you love it and how it resonated with you.

Example:

Jim, appreciated your post today. I am a former seminary student who thought full-time ministry was the only way to truly serve God. But in 1996, I met an entrepreneur and mentor who said, "My ministry is to glorify God by being excellent in the marketplace." That statement completely transformed my perspective. And it's the driving force for me as a founder today. My business is my ministry. It seems you have a similar outlook.

4. Catching Up

Whether it's a simple hello, discovering a shared background, or following up on life changes, look for opportunities to “catch up.”

Where do you find these opportunities?

Some will immediately come to your mind. But if you’re blanking out, a good starting point is downloading your LinkedIn connections list to find people you’d like to catch up with.

(Here’s how to download your connections 👉 https://www.linkedin.com/help/linkedin/answer/a566336/export-connections-from-linkedin)

Then, personalize your message.

Examples:

Ex. 1:

Hi Maria, it's been a few months, and wanted to say, ‘Hi.’ Let's catch up soon!

Ex. 2:

Hi Steven, We've been connected on LinkedIn for several years. But we must have just missed each other at Westminster Academy. (I graduated in 1991.) Small world, my friend!

Ex. 3:

Hi Matt, thinking about you, my friend. How are things going with your move to Texas? Have you made the move yet? Have a great week!

5. Company Page Follow

This strategy is for the company owner or the designated page manager.

When someone follows your company page, it's an opportunity to initiate a personal connection. Here are two approaches:

Standardized:

Hi Kathy,

A quick note to say thank you for following our Systematic Selling company page.

Appreciate you 🙏

All the best,

Sean

Personalized:

Hi Steve,

A quick note to thank you for following our Systematic Selling company page.

Really appreciate you 🙏

Hope you and Denise are recovering okay from the impacts of Hurricane Helene.

Have a great weekend.

All the best,

Sean

6. Direct Request

Notice in the following examples that these requests are not cold. I have already interacted with the person before sending a Direct Request DM.

Examples:

Ex. 1:

Hi Phil,

Noticed you were hiring for an Account Executive role.

You likely already have your onboarding and training systems for new sales hires dialed in internally.

But would you ever be open to connecting on Zoom to explore best practices that I've seen work well for setting up new reps for success?

(Systematic Selling has identified the 7-step cycle that the elite sales teams follow.)

[Company] is probably already doing them, but perhaps the conversation will generate new ideas that could be valuable to you and the team.

Either way, I look forward to watching you guys crush it.

All the best,
Sean

Ex. 2:

Hi Bob,

You’ve been an awesome follow on LinkedIn, and I really appreciate your engagement with my posts.

I’m curious…Would you be open to joining me as a guest on an upcoming episode of the Systematic Selling Podcast? (https://www.systematicselling.co/podcast)

Our audience is growth-minded SMB founders, owners, and sales leaders.

If you’re open to it, I would love to dig into:

- Your formative years that helped shape the entrepreneur you’ve become.

- Your origin story for [Company]

- Your GTM strategy to get [Company] where it is today (what worked, what didn’t)

- The lessons you’ve been learning along the way.

Let me know your thoughts, and we can nail down the details from there.

If, for any reason, the podcast or the timing is not a good fit right now, no worries at all. Just let me know.

Thank you, Bob.

My best,

Sean

7. Holidays/ Special Days

Holidays, birthdays, anniversaries, or ANY special day are “free shots on goal” for building a relationship with a simple DM.

Example:

Hi Phil,

Wishing you and yours a wonderful Christmas holiday!

Really glad we connected in 2024.

Here’s to a prosperous 2025 👊

Gratefully,

Sean

The Bottom Line

While not every DM will lead to a meeting, and not every meeting will result in a sale, this systematic approach to relationship-building creates a sustainable pipeline of opportunities that emerge naturally through consistent contact and interaction.

The Next Step

How do you nurture these new relationships beyond DMs?

We’ll discuss that in Part 3 of “Selling on LinkedIn” in the February 28th edition of the Systematic Selling Newsletter, where we’ll talk about Your Engagement Strategy.

See you then 👊

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Sean M. Lyden is the founder and CEO of Systematic Selling, a sales systems and coaching company for growth-minded SMB founders and owners looking to scale their sales (without the chaos).

PS: Our Book is Now on Audible👇

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