April 1, 2026

If you've spent any time on LinkedIn, you know what the inbox usually looks like: generic openers, fake compliments, and a pitch in the first sentence. Messages that were clearly copy-pasted to 500 people and somehow still made it through.

Most cold outreach is so bad that replying to any of it sounds like a prank (even when it's not April Fools).

But every so often, someone gets it right. And when that happens, I screenshot it.

I study these messages to understand why they land and send them to my team. What made me pause, think, and actually reply back? Because that's the whole game, and it's what we obsess over for our clients every week.

Here are three that made the cut recently, and exactly what they got right:

DM #1: The 'pick a lane' question

Why this worked for me:

• Relevance without being generic. He referenced something specific about how I show up on LinkedIn, not just my title or name. It signaled he actually scrolled through my profile, which is rare and instantly disarming.
• His question had two clear pathways. Instead of a vague “I’d love to connect and learn more about your work,” he gave me something easy and specific to respond to. Two options = low friction. I could pick a lane.
• The conversation felt mutual. His questions showed insight, not just interest in what he could extract. I knew a pitch might be coming eventually, but I was also learning from him along the way.

DM #2: The high-value check-in

Why this (mostly) worked for me:

• I've been connected to this person for a few years, but have never bought anything from her. Her warm check-in message led with giving, not getting. No ask or pitch, just an offer to be useful. That’s a complete pattern interrupt from the usual “I’d love to grab 15 minutes” opener.
• The question was open but bounded. She didn’t ask me to fill out a form. One topic. That’s easy. I can answer that in 10 seconds.
• Buttttt I would drop the rocket emoji and make it more specific to a resource she thinks I would find helpful based on my topics and expertise.

DM #3: The potential before the pitch

Why this worked for me:

• Proof he actually listened, or at least had his AI Agent listen for him. He referenced a specific episode and a specific concept from it, not just “I love your podcast.” That takes 5 extra minutes and communicates respect for my time immediately.
• A story, not a pitch. He didn’t say “we offer ghostwriting services.” He showed me a result through a relatable narrative. I could see myself in the story before he ever made an ask. Somehow this guy knows I have two half-written books on my nightstand and five in my head.
• The close was confident without being pushy. “I’ve been thinking about how your content could do the same.” That’s it. No calendar link or call to action. Just a planted idea. He trusted me to follow up if it resonated.

These worked for me because they signaled relevance, value, and respect for my time. They offered value and then put the ball in my court.

Not long ago, I sent you the recap of a conversation I had with a guy from Hinge, and how the best relationship advice maps almost perfectly to outbound strategy.

The short version: humans can smell desperation and misalignment. Good messaging meets people where they are. These three DMs prove it in practice, and it's the reason why our clients average a 30%+ positive reply rate on their LinkedIn outbound campaigns, far outpacing the industry average of 10–20%.

It’s not magic, but it takes an extra 3-4 steps of work that most people don't want to do. We hand-select people who are actually the right fit. That specificity changes everything downstream. We comb through profiles before a single word is written. What did they post last week? What’s their company going through? What are they proud of? The research IS the message. We craft messages that are hyper-targeted to that individual. The result: messages that don’t get ignored, deleted, or reported as spam, because they don’t feel cold.

3 Easy Ways to Try Cold DMs This Week

You don’t need a full campaign to start. Here’s where to begin:

1. Build a niche list of 50–100 people. Resist the urge to go broad. Smaller and more targeted = higher reply rates, better conversations, and less wasted energy. Think: who is the perfect person for what I’m offering right now?

2. Connect before you message. Follow them. Engage with a post. Let your name become familiar before you land in their inbox. Warm up the relationship even slightly — it changes the context of everything that follows.

3. Send a first message that signals relevance and value, not a CTA. Your first message is not a pitch. It’s an introduction. Show that you’ve done your homework. Ask something genuine. Offer something useful. Trust that the conversation will do the selling, because it will, when you have something valuable to offer.

And if you need our team to handle this for you, just reply to this email and we'll get the ball rolling.

What’s the best cold message you’ve ever received or sent? I’d love to hear about it!

Keep experimenting,

Brynne

p.s. We're only TWO weeks away from the next Thoughtful Leaders cohort, and Week 4 is all about intentional messaging where I break down more examples like this and give you the tools to get started. Register here if you're ready to show up on LinkedIn thoughtfully and intentionally.

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