Why leading with a pitch fails in cold email

I just deleted 147 cold emails without reading them. Here’s what they all got wrong: Every morning, my inbox looks the same. A flood of pitches from people trying to sell me something. Most days, I just mass delete them. But this morning, I decided to actually read through them first. Within 5 minutes, I spotted a pattern. Everyone was making the exact same mistake. They were all trying to close the deal. ALL IN THE FIRST MESSAGE 🥵 Let me show you what I mean (with two small examples): APPROACH A: "The Wall of Text" Send 100 cold emails with full pitch, calendar link, and case studies. • 3 people open • 0 responses • 0 intros This looks exactly like the 147 emails I just deleted "Hi [Name], I noticed your company is scaling fast! We help companies like yours optimize their marketing stack through our proprietary AI technology. Our clients see 300% ROI within 90 days. Here's my Calendly link to book a 15-min chat: [LINK]. Looking forward to connecting! Best, [Name]" BORING!!! APPROACH B: "Micro Conversations" Same 100 prospects, broken down into micro-convo's. Email 1: "Do you know [mutual connection]?" • Send 100 • ~40 open • ~20 respond Email 2: "They mentioned you're scaling your marketing team. I'd love to connect about [specific thing]." • Send to 20 who responded • ~15 continue engaging Email 3: "Would you mind if they made an intro?" • Ask 15 engaged prospects • ~10 intros Final score: • Approach A: No intros • Approach B: 10 intros How to Apply These Lessons (Tactical Summary): 1. Focus on Micro-Conversations: Break your cold outreach into smaller, manageable steps. Build rapport before making any asks. 2. Personalize Everything: Reference mutual connections, specific company milestones, or shared interests in every message. 3. Play the Long Game: Aim for replies in the first message.. not conversions. If you’ve been struggling with cold outreach, you might just need a new approach. Give this one a try and lmk how it goes.

I’m tired of connecting with someone on LinkedIn only to get pitched their product or software within five minutes. Yes, sales matter. But relationships matter more. When the first message is a pitch, it tells me you’re chasing transactions, not building trust. It skips the part where we actually get to know each other. Where we learn if there’s alignment. Where we find out if what you’re offering even solves a real problem. The best partnerships I’ve been part of didn’t start with a cold pitch. They started with a conversation. Ask a question. Learn what matters to me or my team. Offer something helpful before asking for time. It’s not about playing games. It’s about respecting people and earning the right to share what you do. Sales will always be part of business. But if you’re not building relationships, you’re building a house on sand. #SalesWithIntegrity #RelationshipsFirst #LinkedInCommunity #TrustMatters #BusinessDoneRight #CustomerExperience #ListenBeforeYouPitch

I’ve trained hundreds of sales reps over my career. Here’s the exact framework I use to write good cold emails from start to finish: 1. Lead with the pain not the pitch The goal of a cold email is to start a conversation, not close the deal. It’s to reflect back a real pain your buyer is already feeling often before they’ve articulated it themselves. No one cares about your product. Especially not in the first touch. They care about themselves and their problems. The biggest mistake I see reps make is trying to close too early. They shove value props, case studies, feature sets, and “we help companies like…” I always come back to this: “No pain, no gain, no demo train.” You’re not here to educate. You’re here to trigger recognition. To make them nod and go: “Yeah, we’re feeling that.” 1. Write like a human The best cold emails don’t have long intros. No “hope this finds you well.” Just a clear, honest attempt to connect over something they care about. Let’s say we’re targeting agencies running 10+ client accounts. Here’s how I’d start: “Hey — I saw you’re managing multiple clients. Curious if you’ve had to deal with deliverability issues lately, especially with the new Google/Microsoft changes. Is this on your radar?” That’s it. No pitch. No product. Just a relevant question that hits a live pain. You don’t need clever. You need to be clear. 1. Structure matters (but keep it stupid simple) I’m not into formulas. You don’t need a 7-step framework to write a good email. You need to understand the buyer and speak to them like a peer. Think about it like this: Line 1: Show you’ve done your homework. Line 2: Bring up a real, relevant pain. Line 3: Ask a question that invites a reply — not “yes.” If your email looks like a blog post, you’re doing it wrong. The goal isn’t to explain. The goal is to start a conversation. 1. Use follow-ups to build narrative (not nag) Most follow-ups sound like this: “Just bumping this to the top of your inbox.” “Not sure if you saw my last message.” Useless. Instead, think of your cold email sequence as a way to diagnose pain over time. Email 1 brings up the initial problem. Email 2 digs into what happens if it doesn’t get solved. Email 3 introduces that you might have a solution, if they’re open to it. Each message earns attention and adds value. Follow-ups shouldn’t be annoying. TAKEAWAY Conversations > conversions. Relevancy always wins.

Most reps start cold outreach with: "I saw your company..." Then wonder why they get ignored. I’ve reviewed 1000+ cold outreach messages. The ones that worked all followed the same pattern: INSIGHT → PAIN → QUESTION Most cold outreach fails because you lead with YOUR agenda: "I'd love to show you our solution..." "I think we could help you with..." Prospects immediately think: "Another sales pitch." Delete. The framework that gets 15-20% response rates: Step 1: INSIGHT Lead with something they don't know about their situation. Share an industry trend or benchmark. "Most VPs we work with don't realize that 60% of their pipeline stalls because..." Why insights work: They position you as an expert, not a salesperson. They create curiosity instead of resistance. Step 2: PAIN Connect that insight to a potential problem they might be experiencing. "...which means you're probably dealing with longer sales cycles and more 'no decisions'..." The key word is "probably." This feels consultative, not presumptuous. Step 3: QUESTION Ask if they're seeing something similar. Not if they want a demo. "Are you seeing similar patterns in your pipeline?" Why questions work better: Questions start conversations. Asks trigger resistance. Full example: "Hi [Name], Most sales VPs don't realize that 73% of deals stall because reps are selling to champions instead of decision makers. This usually shows up as lots of 'positive feedback' but deals dying in committee. Are you seeing similar patterns where reps have great conversations but struggle to get deals across the finish line? Best, [Your name]" What this accomplishes: ✅You sound different from every other rep ✅You lead with value instead of ask ✅You focus on their problem, not your solution The psychological shift: Instead of "This rep wants something from me," they think "This person might understand my situation." Common mistakes to avoid: ✅Don't make the insight too generic ✅Don't make the pain too assumptive ✅Don't end with a meeting ask The result: 15-20% response rates because you sound like a consultant, not a vendor. Stop pitching. Start consulting. — AEs! Check out the 3 questions that break through price objections here: https://lnkd.in/gbBjgxxS Sales Leaders: Want to install a revenue system that your reps can follow? DM me.