Why long cold emails get buried in Outlook

“Keep cold emails less than 5 sentences because people have the attention span of a goldfish.” I hear this advice all the time. But it’s not quite right. People don’t have short attention spans. They have short interest spans. If your email doesn’t illuminate a meaningfully different idea related to a problem your prospect doesn’t know about, short won’t save you. If it’s specific, relevant, and speaks to what they’re actually dealing with? They’ll read every word. Let’s compare: ⸻ Short, but generic: “Hey Sarah, saw you’re hiring 4 SDRs. Wondering if you’d be open to a quick call to explore how we can help with SDR ramp time. ACME reduces ramp time by 28%. Let me know!” That’s short. But it’s also forgettable. It doesn’t show you understand her world, her workload, or her hesitation. ⸻ Longer, but relevant: “Hi Sarah, Looks like you’re hiring SDRs, which suggests onboarding is eating up 10–12 hours a week per manager. The process typically involves call reviews, shadowing, and quick feedback in Slack or Gong. It works but only when there’s time. And when things get busy, coaching slips. Teams try templates or one-off trainings. But those don’t fix the root issue: reps don’t know how to think on live calls, they’re just memorizing lines. Reps use ACME to practice daily, so coaching time is used to fine-tune, not build from scratch. No new tools to roll out. No extra work for your managers. Want to take a peek?” That’s longer. But it shows understanding, insight, and empathy. Don’t aim for five sentences. Aim for five seconds of “this person gets me.”

I've reviewed 300+ cold emails for clients this quarter. There's a ton of variability in the prospect roles my clients are targeting (CIOs, CROs, Heads of Maintenance, Repair & Operations, CMOs, Chief Sustainability Officers, Directors of Engineering, Directions of Operations, etc.). Yet, there were 2 cold emails I saw over and over. #1 - The Kitchen Sink "Dear prospect, my name is Jen and here's a small novel about who we are, what we do, and why we're great. Are you free next Tuesday for me to tell you more about us?" Word count is 200+. Reading time is 90+ secs. Bullets. Lots of long sentences, big words, & commas. Large chunky blocks of text. I used to send these, too. I thought the job of a cold email was to impress them with what WE do. I didn't know exactly what would impress them, so I threw everything in there. I left no juice for my follow up emails, so I resorted to "bumps" and "thoughts". What I didn't know is that when a reader opens these emails - it screams effort. Effort is our enemy. Ever heard the saying "if you want to be interesting, be interested?". Cold emails don't have to sell "us" yet. Job #1 is to show the prospect we have a unique POV into why them, why now. #2 - The Love Bomb "Dear prospect, I'm so impressed with this overly generic thing I found about you after doing 3 seconds of research that has nothing to do with what I'm emailing you about. Anyway, I'd love to have the chance to schedule time with you so I can understand your priorities and then use that information to sell you something." It's understandable why WE'D love to have prospects tell us their priorities. But, consider it from the prospect's side. Does sharing publicly available information about their company priorities sound like a good use of their time? And, forced compliments or forced, generic personalization doesn't have the desired effect. It screams "I know I'm supposed to personalize, so I'm checking the box". If you have something personal AND relevant to the message - great! If you have something personal, but irrelevant to the message? Throw it in a PS. Leaders - if you haven't done so, ask your AEs, AMs, and SDRs to submit a cold email for one of their target accounts. It will help you understand what beliefs & assumptions your reps are operating under.

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.

Long, complex emails don’t make me think you're smart. They tell me you don't understand basic buyer behavior. Your prospects aren’t reading your sales emails. They’re skimming. They’re standing in line at Starbucks, cleaning out their inbox. They’re looking for a reason to delete, not to reply. If your email doesn’t pass the 1, 10, 100 test - it’s getting ignored I teach this framework to every sales team I work with. It’s simple and it works. Here’s how to apply it: 1 = One clear call to action Do not ask for a meeting, feedback, interest, and availability in the same message. You get one ask. Make it count. 10 = The first 10 words must earn attention This is your subject line + preview text. It’s the only thing your prospect sees before deciding to open or delete. If those 10 words don’t create curiosity or show relevance, it’s over. 100 = Keep your total word count under 100 The average exec scans an email for 3–4 seconds. If they can't get context immediately, your email is an auto-delete. Make it short. Make it relevant. Make it easy to reply. The 1, 10, 100 Rule isn’t about oversimplifying your message. It’s about respecting how buyer's interact with cold email so you can deliver more value and earn more engagement. 📌 Remember RELEVANCE is essential. Don't think a well-formatted email replaces the need to say something that matters to the reader. ✨ Enjoyed this post? Make sure to hit FOLLOW for daily posts about B2B sales, leadership, entrepreneurship and mindset.

Your email has under 3-sec to capture attention. So if your cold outreach sounds like: “Hi Linda - hope you’re well. I’m part of the account team aligned to XYZ and we work with companies in your space to help streamline…” ❌ You’ve lost them. Because here are the facts: 30% of prospects look at your email for 2 seconds 41% look for 2 to 8 seconds 29% for > 8 seconds [source: Litmus] A big reason this is the case is because the majority of cold emails sound like - first 90-characters are too salesy - lead with the solution, not the problem - jumbled up, long and not mobile friendly - >100 words rambling on about the product - your language (features) vs theirs (problems) - buzzwords, capabilities + product jargon galore - hard for them to understand what you’re saying ………………………………… The key is to flip the script on each of those points Let’s take this one for example “Hi Linda - see you’re using SAP, Salesforce and other apps to run your business. Not sure if you see this, but we find tech leaders often rely on excel, ETL + manual coding to tie data together. It can be tedious and error prone, leading to project delays. With [solution], X company avoids having to cobble up data from different systems. They can easily integrate their key apps with a clean front-end in a low-code environment. Leading to integrations taking hours vs weeks. Worth a chat?” ……………………………… Cold email isn’t dead. But if we don’t lead our message with the prospects language, it’ll be on its last legs.

Why your emails are getting ignored. If you are sending cold emails to school and district leaders and not getting responses, you are not alone. The problem is not necessarily what you are selling. It is how you are positioning it. Every week, school decision-makers receive hundreds of sales emails from companies. The ones that get ignored all make the same mistakes: They are generic. “We help schools improve student engagement with innovative learning solutions.” They sound like every other pitch. “Can I get 15 minutes on your calendar to show you how we can support your district’s goals?” They make it about the vendor, not the school. “Our platform helps districts achieve better outcomes.” How do you get your email opened? Be specific and show that you understand their district’s needs. “[XYZ] Grant will be open for applications next month and it looks well aligned to [district's strategic goal]. Can I walk you through the steps to apply and provide additional resources?" Make it about them. Instead of pushing a meeting, offer something valuable. “A few districts in your state are funding this through [grant name]. Want me to send you details?” Keep it short. If your email looks like a wall of text, it is getting deleted. Say less, get to the point, and focus on relevance. School leaders do not respond to sales pitches. They respond to helpful, well-timed outreach that solves a real problem. If your emails are not working, rewrite them with one goal in mind: making it easier for the district to say yes to meeting with you.

It only takes a prospect 3 seconds to scan your cold email. If they can't immediately understand what you want, they WILL delete it. Long emails feel like work to read. And busy executives don't have time to decode your novel-length pitch. When you explain everything upfront, you eliminate curiosity. No curiosity = no reason to respond. Whereas, shorter emails create urgency. And they force prospects to engage if they want more information. Here's what works right now: "Hey [Name], noticed you're the founder at [Company]. Mind if I share a quick video showing how we helped [Similar Company] automate their client onboarding process?" Two sentences, one observation and one specific offer. You’re not looking to close the deal in your first email. You’re just looking to get a response. My view on long emails is that they try to do too much. And essentially they overwhelm prospects with information they didn't ask for. Whereas, short emails do one thing well: They start conversations!! Just keep in mind that when you focus on one specific result for one specific type of client, your emails convert.