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How to Approach LinkedIn DMs

Prospecting on LinkedIn isn't that different than sending a cold outreach email. Similar practices apply. We break down our effective approach here.

A sales rep sits in a lavender field on a laptop sending messages on LinkedIn.

Reps love to ask us how to approach LinkedIn prospecting. Our data is specific to sales email. That said, we are in the business of helping sellers write more effectively.

So... below we put some thoughts down on how to approach selling on LinkedIn.

Worth noting: No channel should live in a vacuum. This advice isn't to be used in lieu of any other channel.

As you'll see, we weave email in at the last touchpoint.


Let me start with three main points:

  1. A LinkedIn connection request should be the first touch point within a sequence. This allows the invite time to be accepted. You should also hit the follow button (maybe even the bell) so you don't miss content from them that you could engage with. ~1% of people post regularly, so don't worry about it clogging your notifications. Even if it does, that's a signal you need to be spending more time on the platform.
  2. You should not include a note in your connection request. Hot take, but this is based on our experience. You'll get less accepted requests if you include a note. Why? You're more likely to give them a reason not to accept.
  3. Odds are your connection will last longer than your current job. There is nothing more cringe than going to a connection a couple years later and seeing an absolutely atrocious pitch. (Yes... we've lived this.) Say no to pitch slapping, automations, etc. You're burning bridges.


If #2 bothered you, let's make amends by talking about how to thoughtfully engage people.

For starters, if someone is actively posting and engaging on LinkedIn. Like and comment on their stuff. Hopefully that's obvious, and it isn't why you came here.

LinkedIn DM Framework

Here's a framework for writing a compelling DM:

A) Start with an observation

B) Tie that observation back to an insight or challenge

C) Ask a question

... sound familiar?

It's because it's pretty much identical to how we suggest starting a cold email. You have to give the reader context on why you're there.

Here's where LinkedIn becomes a little different.

In a cold email you should shy away from open-ended curiosity, non-"to-do list" items, personal experiences. On LinkedIn, you should lean into these things.

The inbox is a to-do list. Social media is more akin to a conference.

Want an example?

"Hey {prospect}, saw you're coming into your role at {SMB Company} after spending your career mostly with enterprise orgs like {big company}.Have you found how they approach {topic} to be dramatically different?"

You're not pitching. You're starting a conversation.

There are hundreds of ways you can approach starting this dialogue. It could be work experience (see above). It could be something someone else at the company posted. It could be something going on at the company in general.

If you approach it more closely to how you're approaching your cold email, that's okay too.

Avoid going off about yourself. You're looking to start a conversation about the topic — this isn't a pitch.

Your goal is conversation.

Some disagree with this. They like to just be efficient with a short pitch.

Your challenge is the window size is microscopic. You basically have 30 words max. The closest we'd get to a pitch is:

"Will, saw the sales org grew like crazy this past year. How are you feeling about the team's email reply rates?"

Fits nicely with the chat box, but opens up a lot of room for a follow up.

Compare LinkedIn DMs to Sales Email Cadences

How does this all fit into a sales cadence or sequence?

It's not one size fits all. Some persona are more active on LinkedIn than others. If they are more active, maybe dedicate a few touch points to LI.

A good second touchpoint would be an audio note, restating your reason for reaching out.

You can also use LinkedIn's native video tool. I prefer their native tool because it doesn't bounce someone to a third party page.

Be sure to write a quick summary below, so that they can get the gist with or without watching or listening.

If they're not responding, we suggest capping outreach at three messages. A third note should push them back to email.

Something like,

"Hey, given {reason I reached out} I shot you an email. Did you have any feedback on it?"

Give it a swing and let us know how it goes.

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