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Stilettos in the Sandbox · Oct 19, 2025

The ABCs of DMs: How I Start Conversations That Actually Convert

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Tara Lassiter · Stilettos in the Sandbox

Too eager. Too generic. Too long.

Everyone’s busy trying to say the right thing, when what people really want is to feel seen.

If you’ve ever stared at a blank screen, wondering how to start a conversation without sounding like a bot or a beggar, you’re not alone. And you’re not bad at sales, either. You’re just sending DMs like it’s still 2018 (or like the bros hawking AI/spray and pray tools).

So don’t take it personally. Nobody’s ignoring you because you’re not good enough (you’re more than enough).

They’re ignoring you because your message looks like everyone else’s.

I’m juggling homeschool and a home-based business. I don’t have time to waste on tactics that don’t work (who does?).

Here’s how I write messages that stand out in a crowded inbox and get responses like this:

Expandi’s State of LinkedIn Outreach report found personalized connection requests get 3–5x higher response rates than generic ones.

Also, Skylead’s data shows conversation-led messages outperform pitch-first DMs by over 40%.

Even more, according to Attentive’s Global Personalization Study, 81% of people ignore irrelevant outreach, while tailored messages directly increase both loyalty and sales.

So no, your prospects don’t hate your messages. They don’t mind your interruptions, either.

They just hate being marketed to when they could be talked to.

Here’s the simplest, most powerful way I’ve found to turn a cold DM into an actual conversation.

I call it The ABC Method (and it’s not short for Always Be Closing 🙄):

A — Acknowledge

Show you’ve done your homework. Mention something specific they’ve said, shared, or achieved.

“I saw your post about scaling your team without losing culture. That’s such a tricky balance.”

B — Build a Bridge

Create a connection between their world and yours.

“That’s actually what my clients have been navigating this year as they grow.”

C — Call to Conversation (with Curiosity)

End with a genuine, low-pressure question.

“Curious, how are you keeping the connection strong as you scale?”

That’s it. No awkward pitch. No paragraphs.

Just three simple beats that show respect, relevance, and real curiosity.

The ABCs work because they let you personalize without performing.

You’re not proving your worth, you’re inviting conversation.

When I say this isn’t just “vibe-based strategy,” I mean it.

According to Dr. Robert Cialdini’s research on reciprocity, people are wired to respond when they feel acknowledged.

The classic Harvard Xerox study (Ellen Langer, 1978) found that when people added a reason, any reason, after a request (“because…”), compliance jumped by up to 60%.

Similarly, the Global Risk Community’s 2024 study on curiosity showed that curiosity triggers dopamine, increasing focus and engagement.

Translation:

When you make someone feel seen, give them a reason to care, and leave a small loop of curiosity open, they can’t not respond (eventually).

That’s not manipulation. That’s just being more human than your competitors. It may take a few days, weeks, or months to get a response. Everyone’s busy, but they’ll notice that you’re different, and that’s what makes them come back.

One of my clients came to me convinced she was “bad at outreach.”

Her messages were long, polished, and completely forgettable.

She was doing what most of us are taught: lead with credibility, talk about results, and show value.

It read like a résumé with punctuation.

We replaced her scripts with the ABC framework.

Her next message went something like this:

“Hey, I saw your post about juggling client delivery and new business. What you said about systems really hit home. I help founders get new business with strategic content, so I was curious, how are you balancing the two right now?”

One sentence of acknowledgment.

One bridge of relevance.

One curious question.

Her reply rate that week? 30%.

And her tone? Lighter. Confident. Conversational.

She wasn’t selling anymore. She was seeing.

That’s the point: you don’t build pipelines. You build relationships that fill them.

I see so many founders and consultants who spend more time rewriting DMs than sending them.

If that’s you, please stop.

DMs aren’t essays. They’re invitations.

Your goal isn’t to impress someone in one message. It’s to start a micro-conversation that leads somewhere natural.

Try this:

  • Set a timer for 20 minutes.

  • Send 10 ABC-style DMs.

  • Don’t over-edit.

  • Don’t over-explain.

  • Just acknowledge, bridge, and invite curiosity.

Even if three people reply, you’ve opened three doors you wouldn’t have yesterday.

Those doors lead to calls, collaborations, referrals, friendships, and actual momentum.

Emails are crowded. DMs are conversational.

According to Expandi’s 2025 data, average LinkedIn DM reply rates hover around 35–45%, while cold email averages 12–18%.

That’s not a small gap. That’s a chasm.

Somehow, people still cling to email because it feels “professional.”

But professionalism isn’t platform-dependent, it’s purpose-dependent.

A well-crafted DM that acknowledges someone’s work is infinitely more professional than a 300-word pitch they never asked for.

So buckle up, buttercup, we’re in the trust economy now.

And curiosity is your currency.

You don’t have to sound like a closer to close.

You just have to sound like a person who’s interested, not interesting.

Because at the end of the day, sales is simply a structured conversation.

Despite what you may believe, structure doesn’t kill connection (or creativity), it gives it somewhere to go.

When you Acknowledge, Build a Bridge, and Call to Conversation, you’re not manipulating behavior. You’re modeling respect.

Respect scales faster than any funnel.

And that’s what makes the ABCs timeless.

If you don’t have a waitlist but you’ve been overthinking your DMs, here’s your challenge:

This week, send five ABC-style messages to people you actually want to talk to.

Don’t pitch. Don’t attach links. Just… start the conversation.

Your future clients are one DM away if you can just sound like a human.

Conversations are an underrated KPI. Start there.

  1. Expandi: State of LinkedIn Outreach (H1 2025)

  2. Skylead: LinkedIn Outreach Trends 2025

  3. Attentive: Global Personalization Study (2025)

  4. Global Risk Community: Why Selling Through Curiosity Works

  5. Langer, E., Blank, A., & Chanowitz, B. (1978). The Mindlessness of Requested Behavior: The Xerox Study.

If today’s post hit home, let’s keep the conversation going. You can:

Read the original on taralassiter.substack.com

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