DMing without feeling salesy.

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Hey, Reader,

A founder asked me this in the DMs recently…

“How do I DM people on LinkedIn without feeling salesy?”

And if you’ve ever hesitated before hitting send…you’re not alone. Many of us can relate.

Isn’t this the fear?

Sounding pushy and transactional...

Sounding like THAT person.

Ugh. I know I don’t want to be that annoying woman waving her LinkedIn services around, trying to get someone to sign on the dotted line.

And I’m willing to bet you don’t want to be that person either.

So instead of staying stuck there, let’s break this down in a very tactical way that feels helpful. Here's my process...

Watch for the right signals.

DMs feel awkward when they come out of nowhere, don’t they?

But they feel much more natural when there’s already been some form of interaction.

Now I'm not necessarily saying never make a cold call (sending a message to someone you've never really had much contact with) because maybe that works for you.

But the majority of the time before I reach out to someone, I try to make sure at least one of these green flags is in play...

They viewed my profile.

They commented on one of my posts.

They liked one of my posts.

They replied to a comment I left on their post.

None of these guarantees a conversation. But all of them signal awareness, and awareness turns outreach into warm outreach.

Warm outreach is what I prefer when given the choice between it and cold calling.

Warm outreach is when someone knows who you are… or at least your name feels familiar when they see it.

So when a message shows up, it doesn’t feel random.

Instead, you tend to think, "Oh, hey, I know (Insert name). I've seen he/she comment on my posts a few times."

Why most DMs feel salesy…

Most salesy DMs feel icky because you can sense the other person’s agenda right away.

That’s been my observation.

Sometimes they start off warm…

But before you know it, the message ends with a link prompting you to sign up or make a purchase.

With real relationships, links come after relevance is established.

People can feel when the goal is connection and when it’s just conversion.

And look, I get it. Most of us have services to sell. (Me, too!)

But I’m willing to bet you’d agree that you only want to work with people you can actually help.

And how are you supposed to figure that out if you’re not trying to understand the person, their current situation, and what they’re focused on right now?

When someone leads with an offer out of the gate, it tells me they haven’t taken even a few seconds to qualify me.

Where are the questions?​
​Where’s the interest in what I’m actually working through?

It’s off-putting.

It doesn’t work.

And it’s exactly why so many of us fear sounding salesy because we don’t want to be associated with this vibe.

Which is fair.

So here’s my rule I like to live by...

Don’t lead with your offer.

It needs to be earned.

What to consider instead.

The easiest way to not feel salesy?

Be a human and act like you would when trying to meet someone new.

And please don't default to a template that doesn't fit your personality.

Just be real and keep it simple at first.

Here are some of my most recent initial DMs to folks, pulled directly from my messages...

The follow-up after an event...

When you see someone like your comment on another post...

When someone likes your post and you notice something you have in common...

Take the pressure off and just try to initiate contact.

It's pretty much the same way I’d start talking to someone if we met at a conference and I recognized their name from LinkedIn.

Most of the value here is in listening. Actually listening.

And with more back-and-forth, it’s the depth of the conversation that builds trust.

Once you've built trust, you can ask whether it makes sense for the two of you to jump on a call to talk further.

A few important nuances people overlook in the DMs.

This part matters, and I think it's worth calling out while we're on the subject of DMs...

Curiosity without authenticity still feels fake.

If you’re clearly following a script, people can tell.

So, do some more self-reflection and notice what you say when you talk to people.

If it helps, actually study the transcripts from the AI notetakers in your meetings and watch the flow of those conversations.

How do you actually speak with another person? What are the words you use?

Use that as a guide to sound more like you.

And I have to bring it up...

Sending DM after DM with no response is not the answer.

Silence can actually yield a lot of information.

If you're not hearing back from someone, maybe they're not on LinkedIn much.

Or it could simply mean, “Hey, I’m not ready to chat right now.”

If you still admire what someone stands for even though they're tough to get a DM response from...

Comment thoughtfully on their posts.

Add value where it’s visible.

But please don’t hound them and overdo it. If nothing comes from trying to comment on a few of their posts...

Cool your jets.

And move on.

There are a billion+ people on the platform, and I'm pretty sure you won't run out of people to speak with.

It's ok to be clear about your value.

Being non-salesy and approachable doesn’t mean being vague.

If you have something helpful to offer, it should come up organically when the timing is right.

Not from desperation.
And not from trying to force anyone into a call.

When you’re genuinely trying to help, that energy is obvious.

And when the fit is there, the conversation starts to move towards how you might work together, if it’s mutually beneficial.

But you can’t rush it.

At the same time, you also need to know when to move on.

Not every DM conversation needs closure.

You can usually feel when a thread starts to drag and when someone keeps asking for more without respecting your business boundaries.

And in those moments, it’s ok to be direct.

It’s ok to remind them what you offer and that it’s a paid service.

Most people respect that.

Because many of us are in the same boat.

We're building businesses to support ourselves, our families, and the life we want to create, and there's no shame.

That deserves to be honored, too.

Did any of this help? Reply and let me know.

If you missed it...

Amanda Hoffman and I did a LinkedIn Live talking about merch. If you're even considering merch for your business (or thinking you're not "big" enough), listen to this 15-minute segment.​

Or check out my interview with David Young on The Underlayer, where we talked more about what actually shows up before a career shift, the friction felt, and when success starts changing.

Do you have a podcast targeted to other founders or CEOs?

Let me know if coming on to talk about LinkedIn would add value to your audience. I'm interested in doing more of these.

Oh, and for readers in Columbus, I'll be making another appearance to do a Tiger Talk for Innovate New Albany.

It's free! Register Now.​

Thanks for hanging out.

Talk soon,

Find me on LinkedIn, YouTube, or book a 1-on-1 clarity call​

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