he Art of Selling: How to Get Your DM Pitches Right

Why your direct messages sound like a commercial break—and how to fix them

Picture this: you're watching your favourite TV show, completely absorbed in the plot. Just as the protagonist takes a dramatic turn—boom—ad break. Irritating, right?

Now imagine you’re sending cold direct messages (DMs) to potential prospects. That interruption? That’s how your DM can feel to someone on the receiving end when it’s poorly timed, impersonal, or pitch-heavy. It lands like an ad jammed in the middle of a meaningful experience. And it gets tuned out just as fast.

So how do we stop sounding like commercials and start becoming conversations people welcome? Let’s explore.

The Science Behind Ad Fatigue and Cold DMs

Why your DM feels like a pitch before they’ve even read it

Over time, our brains have been conditioned to detect and dismiss sales-y content. We’ve developed cognitive ad-blockers. Just like how we skip ads on YouTube or scroll past sponsored posts on Instagram, we’ve trained ourselves to ignore messages that feel transactional.

Now apply that to cold DMing. When someone receives a message from a stranger, especially one that follows a familiar sales format, the brain immediately categorises it as “pitch alert.” And what follows? Ignore. Delete. Ghost.

Here’s why that happens:

• ❌ We associate unfamiliar messages with spam
• ❌ Familiar sales language triggers defensive behaviour
• ❌ Messages that feel templated lack emotional relevance

But there’s good news. When you’re familiar to them, the reaction flips.

The Power of Familiarity

If someone knows you—or at least recognises your name from their feed—they’re far more likely to open your message. Better yet, they may even want to read it.

People buy from people they know, like, and trust. Which means before you drop the pitch, you need to do the groundwork to make sure you’re seen as a warm, familiar face—not a cold, anonymous message.

Start by:

• Sharing consistent, valuable content
• Leaving meaningful comments on their posts
• Engaging in thoughtful ways long before you slide into their DMs

Build the familiarity first. The pitch comes later.

Selling Isn’t the Problem—Your Approach Is

Why people don’t hate being sold to (they hate being sold to poorly)

Selling is essential. But bad selling kills opportunities. The moment your message smells like a mass-produced pitch, it gets ignored. So how do you flip the script and create a DM that starts a real conversation?

Let’s break it down.

1. Lead With Value

You have one shot at a first impression—don’t waste it on a “Hey, I’d love to jump on a call and share more about what I do.”

Instead, give them a reason to lean in. Share something useful. Respond to something they’ve posted. Offer a perspective that sparks curiosity.

• Bad: “Let’s schedule a quick 15-minute call so I can tell you more.”
• Better: “That post you shared about burnout in founders really hit home. I’m seeing the same with my clients—particularly around [insert insight]. Curious to hear if that’s something you’re navigating too?”

No pressure. Just relevance and value.

2. Personalise It, Always

People can spot a copy-paste job from a mile away. If your DM feels like it could’ve gone to 50 other people, it loses all emotional weight.

Instead:

• Reference something specific about their recent post, work, or business
• Mention a shared connection or experience
• Ask a question that feels tailored, not templated

This doesn’t just build trust—it makes your message human.

3. Focus on Conversation, Not Conversion

Your first DM isn’t the sale. It’s the start of a relationship.

So don’t rush. Create space for back-and-forth. Your role isn’t to close the deal in your first message—it’s to earn the right to have a deeper chat.

Questions build bridges. Value builds trust. Conversations lead to conversions.

Final Thoughts: It’s Not About Persuading—It’s About Connecting

The key to better DM outreach is understanding people, not pushing product

The best salespeople aren’t pitch-perfect. They’re emotionally intelligent. They take time to listen, build rapport, and understand before offering a solution.

So before you hit “send” on your next DM:

• Ask: Have I shown up in this person’s feed before today?
• Ask: Am I leading with something they’ll care about?
• Ask: Am I starting a conversation—or just sending a cold ask?

When you approach DMs with curiosity, empathy, and relevance, you stop sounding like an ad—and start sounding like someone they’d actually want to hear from.

Let’s make cold DMs a little warmer.

Take Action

• Audit your last five DM pitches. Would you reply to them?
• Start engaging with three new people a day on LinkedIn—comment, react, be seen.
• Draft your next DM using the principles of familiarity, personalisation, and value.

And if this post helped reframe your thinking—share it. Tag someone who needs to get their pitch game right.

Let’s turn those commercial breaks into conversations that count.

‍