Stop trying to sell in the first message. You're not Amazon Prime. People don’t open LinkedIn expecting to make a purchase. They’re here to connect. To learn. To be inspired. But too many treat DMs like a checkout page instead of a conversation. Every week, I get cold messages that jump straight into a pitch. No introduction. No context. No attempt to build trust. And the result? Silence. Because when you lead with selling, you lose the one thing that actually drives conversions on LinkedIn: relationships. Here’s what most people get wrong about selling in the DMs. They think speed equals success. They think dropping their offer in message one makes them efficient. But it’s not efficient. It’s lazy. And it rarely works. Over time, I’ve found a better way. It’s slower. More intentional. But it leads to real conversations with decision-makers — and more closed deals. Here’s what I do instead: ↗︎ Step 1: Build trust first Start with something specific about them. A recent post. A podcast. A shared interest. Make it personal. Not robotic. ↗︎ Step 2: Ask thoughtful questions Your goal is not to qualify. Your goal is to connect. Be curious about their goals, challenges, and context. ↗︎ Step 3: Share value before asking for anything This could be an insight, a trend you’re seeing, or a tip they can use right away. When you give first, you earn permission to ask. ↗︎ Step 4: Make the invite to chat feel natural Don’t pitch a 30-minute strategy call. That’s heavy. Just suggest a quick 15-minute call to connect and explore if there’s alignment. ↗︎ Step 5: Follow up without being annoying People are busy, not rude. Give them time. Follow up once or twice — kindly, not aggressively. This approach works. Not because it’s some magic script. But because it treats people like people. So the next time you think about pitching in the first message, remember: You're not Amazon Prime. Trust isn't delivered in 24 hours. Build it first. Found this useful? Hit the 🔔 icon in my profile. Get notified of my next post. Repost it to help 1 new person. ♻️
Why Lazy DMs Kill Buyer Trust
Explore top LinkedIn content from expert professionals.
Summary
Lazy DMs—meaning generic, rushed direct messages—undermine buyer trust by making outreach feel impersonal and transactional rather than authentic. When sellers skip relationship-building and send mass-produced pitches, buyers are less likely to engage, seeing these messages as intrusive and not tailored to their real needs.
- Personalize your outreach: Reference something specific about the person, such as their recent work or interests, to show you’ve done your homework and genuinely want to connect.
- Engage before pitching: Build familiarity by interacting with their content and starting conversations before sending any sales message, so you’re recognized as a trusted contact rather than a stranger.
- Add real value first: Share helpful insights or resources before making any requests, earning the right to ask for time or attention by being generous and relevant.
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Your cold DMs are killing your reputation before you even get a response. I know because I've received 100's of them & sent plenty of bad ones myself. My message requests are filled with "I can get you leads" and "Want to try our tool?" pitches that instantly make me ignore the sender. These low-effort messages are ineffective, and they're actively damaging your professional reputation with every send. When someone blasts me with a generic pitch, I immediately think less of them. That relationship is damaged before it even starts. Now, there is a solution but it requires actual work: Send 10 focused DMs instead of 1,000 spray-and-pray messages. But to make those personalized DM's effective, I suggest you: 1) Create something valuable specifically for them. "I noticed your new products are fire but there's nowhere to buy them online. I built you a simple Shopify page to sell them. Mind if I share the link?" 2) Record a personalized Loom video identifying 2-3 specific issues with their website/content and how to fix them. Both approaches require research and customization. You can't scale them to thousands of messages. But the truth is that 10 well-researched DMs that get 9 responses will always outperform 1,000 generic messages that get the same 9 responses.
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Your outbound doesn’t need another tool. It needs a reality check. I talk to founders and revenue leaders every day who are frustrated. Cold outreach isn’t converting. Calendars are empty. Teams are “busy,” but nothing’s moving the needle. And the default reaction? “Maybe we just need a better tool.” “Let’s try an AI SDR.” “Let’s crank up the volume.” No. You don’t need more tools. You need to stop doing the stuff that’s quietly killing your pipeline. Here’s what I see again and again inside broken outbound systems: 1)Sending lazy "just checking in" follow-ups Translation: "I have nothing useful to say, but please notice me." Every low-effort follow-up erodes trust. It’s outbound spam dressed up as “polite persistence.” 2)Over-relying on automation crutches Prospects can smell a mass-blasted, AI-crafted message from 5 miles away. Automation without relevance = faster brand decay. 3) Leading with your pitch deck "Can I show you our platform?" is the easiest way to get ignored in 2025. If you’re not starting with their challenges, you’re already deleted. 4) Obsessing over volume instead of precision 5,000 messages won’t beat 500 precision targeted ones. Spray-and-pray is a losing game…especially now that inboxes are smarter and buyers are more selective. 5) Measuring vanity metrics that don't pay you Open rates ≠ pipeline. Reply rates ≠ revenue. Your CRM can look “active” and still be ice cold. Pipeline is built on qualified conversations, not vanity metrics. So what actually works today? ✔️ Research-first targeting ✔️ Multi-channel orchestration (email + LinkedIn + warm content) ✔️ Commercial insights over canned CTAs ✔️ Follow-ups that deliver new value, not noise ✔️ Outbound that feels more like a conversation…not a pitch deck in disguise Outbound isn’t dead. But lazy, copy-paste, volume-driven playbooks? Absolutely are. You want better results? Start by respecting the person on the other side of the message. And build a system that’s engineered to convert…not just operate. ✚ Follow for expert GTM insights & growth strategy
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People don't buy from strangers. They buy from people they recognize. Your cold DMs aren't working. Not because your offer is bad. Because you're a stranger. Think about it: would you respond to someone you've never seen before asking for your time, money, or attention? Probably not. But if someone who's been commenting on your posts, sharing valuable insights, and actually engaging with your work reaches out? That's different. That feels like a conversation, not a pitch. Here's what I do now: Before I reach out to anyone, I make sure they've seen my name at least 3-5 times. A comment here. A share there. A thoughtful reply to their story. By the time I DM them, I'm not introducing myself. I'm continuing a relationship that already started. And that changes everything. Because people don't buy from strangers. They buy from people they trust. And trust isn't built in a DM. It's built in the dozens of micro interactions before it. So if your outreach isn't working, maybe it's not your message. Maybe it's your approach. Show up first. Add value first. Build trust first. Then reach out. Do you engage before you DM, or do you go straight for the pitch?
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I didn’t lose that deal because of price. I lost it because I didn’t build trust. Here’s what happened: Last week, a potential client slid into my inbox. Their business looked solid. Their budget was healthy. Their problem? Right in my wheelhouse. I sent over the proposal in under 24 hours detailed, professional, priced fairly. Guess what happened? Silence. I followed up twice. Still nothing. Two days later, I saw they hired someone else. At first, I told myself: “Maybe they just found a cheaper option.” But then I looked closer. They didn’t pick a cheaper offer. They picked someone they’d been talking to for months. Someone they’d commented back and forth with on LinkedIn. Someone they trusted. That’s when it clicked: People don’t choose the best service. They choose the relationship that makes them feel safest. This is why your funnel isn’t just about steps. It’s about signals. Every email. Every follow-up. Every bit of content. Every DM. It either builds trust or breaks it. Funnels don’t convert cold leads. Funnels convert warmed-up, trust-fueled, seen-and-heard humans. And the truth is: No amount of automation can replace genuine connection. So before you ask someone to buy, ask yourself: Have you earned their belief? Because trust isn’t a “nice-to-have” in business. It’s the dealmaker. #funnel #funnelupscale #business #leads
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These 4 mistakes costing you leads and trust. If you’re a coach, avoid these at all costs! I’ve spent years learning psychology and helping coaches grow their businesses. Here are 4 common DM mistakes I’ve seen that ruin trust and opportunities. 1. Pitching too soon. ➟ There’s a 99.999% chance that if you pitch your services in the first message, you’ll lose the opportunity. 2. DMing your posts for likes. ➟ DMing someone to “please like and comment on my post” doesn’t win support, it loses respect. 3. Rushing the relationship. ➟ Asking for an e-meet or sharing contact number in your first message is like asking a stranger for coffee before saying hello. 4. Ghosting their messages. ➟ Ignoring messages is more than rude, it closes doors to potential opportunities. Here are my advice: ↳ Build trust before you pitch. ↳ Engage with their posts every day. ↳ Have genuine conversations in DMs. ↳ Never ignore messages of prospects. ↳ Never be Too Salesy in conversations. As a coach, you might have a great "OFFER". But if prospects ghost you, it’s because you skipped the trust-building phase. When you treat every lead like a relationship not a transaction, your DMs turn into opportunities. P.S. Coaches, your DMs are where clients are won or lost. If you’re neglecting that, then you’re leaving opportunities on the table.