Common Mistakes In Writing Sales Emails

Look, cold call pick-up rates and landing in spam are NOT the reasons why outbound isn't working for you in 2025. How do I know? We've worked with thousands of reps in the last few years: - I see all the sh*tty emails - Hardly any reps leave voicemails - People are afraid to call cell phones - Leaders are afraid to set call activity targets - Product pitching like crazy So why isn't outbound working for you? Messaging. I know. Messaging isn't a sexy topic. But poor messaging is likely why outbound doesn't work for you. Common messaging mistakes: ⛔️ Creating outbound messaging in a silo Mistake: A lone BDR leader, sales exec, or marketing exec creates all the cold call talk tracks and email sequences by themselves. Impact: Messaging sounds generic and has too much personal bias. ⛔️ Marketing or product creating outbound messaging Mistake: A PMM or marketing leader writes all the outbound messaging Impact: Since they've had little (or zero) conversations with real customers, the messaging is super generic ⛔️ Product voice: feature heavy messaging Mistake: Messaging focuses on how the solution works, specific features, etc. Impact: This might work on a webpage, but not in a cold email. Messaging feels super salesy and isn't appealing to execs. ⛔️ Not "chunking up" to business outcomes Mistake: Messaging addresses all of the pains of the user, not the decision-makers Impact: Reps get delegated down to product users and struggle to start sales conversations at the exec level ⛔️ Not leveraging customer conversations Mistake: Not using recorded customer conversations to inform messaging Impact: Messaging doesn't use the customer's language and feels generic. What to do instead: ✅ Build a messaging team Get no more than 10 of the best people together to build common messaging. This should include a few of the best AEs, marketing, customer success, sales leaders, product specialists, etc. And make sure to assign a single person to own messaging. ✅ Live workshop messaging by persona/vertical Run live workshops to work out messaging together. At a minimum, messaging should be created for each specific persona. For enterprise, messaging should be created by persona AND industry. A healthcare security leader speaks a different language than a SaaS security leader. ✅ Build a messaging matrix This is what the end product should look like: Personas → Priorities → Current Solutions → Problems/Impact → Desired Outcomes Now you have something that can easily be repurposed into talk tracks and emails. ~~~ If 2025 H1 pipeline looks thin—and outbound isn't producing results—get back to the basics and start with great messaging. Marketing should NOT own sales messaging. Sales needs to own sales messaging. And everyone needs to collaborate together for great messaging. Agree or disagree? 

It took me 6 years as a commission-only sales rep to make my first $1M in commissions in a single year. If I could go back in time and help my younger self get there faster… I’d tell him to NEVER do these 7 mistakes: 1. Stop being a product pusher You’re not selling the thing You’re selling the results of what your thing does Don’t focus on your product’s features and benefits Focus on the person’s/company's problems and where they want to be. That’s what prospects care about. 2. Sounding needy Sounding desperate will just drive prospects away You don’t want to say things like: “Just tell me what it’s gonna take for you to buy today” (Lowers your status) “If you buy today, we can offer a 20% discount” Etc… 3. Being assumptive too early You don’t want to say things like this too early in a conversation: “When we onboard you, we’ll do XYZ” It will trigger sales resistance with many prospects and cause them to emotionally shut down and throw objections at you. 4. Lowering your status Most salespeople lower their status to “please” the prospect. They build “fake rapport”, say “yes” to everything, and let the prospect have all the “power” You want to do the opposite to come across as the trusted authority, the expert who can solve their problems and get them the results they want. 5. Sounding overly-excited Ever heard “If you’re not excited about what you’re selling, your prospect won’t buy”? That’s a big myth. In fact, there's no data that supports this assertion at all. If you come across as overly-excited and biased, you’ll just trigger sales resistance with many prospects. You want to come across as more neutral, unbiased, collective and detached. 6. Sounding scripted Great salespeople are like great actors/actresses. They know their lines, but they sound natural. You should 100% have a framework/script so you don’t wing it. But you want to understand it so well that everything you say sounds natural. 7. Asking surface-level questions Surface level questions aren’t enough to get your prospect to emotionally open up to you. Don’t ask: “What are your top 3 challenges right now?” Ask: “Off the record, what’s really going on over here that’s caused you to look at possibly changing companies/vendors?” (curious tone)

I've booked over 1,000 sales calls using my "1-2 Punch" cold email strategy, and I'm going to break down exactly how it works: Here's the #1 mistake I see in cold emails: People write a 4-paragraph manifesto to prospects who've never heard of them. Product features, company history, client logos - the whole nine yards. You're basically screaming "I'M HERE TO SELL YOU!". And once you show all your cards upfront, your follow-ups have no ammo left. Instead, here's how my 1-2 Punch strategy consistently books calls: Round 1: The Jab 👊 Think of this as your feeler email. Keep it intentionally brief and spark curiosity. "Are you looking for more qualified sales calls each month?" "We can book 10 sales calls on your calendar each month on a pay-per-call basis. Interested?" These work because they're easy to reply to and don't feel "salesy". One powerful sentence is all you need to create curiosity. Round 2: The Right Hook 🥊 THIS is where you unleash everything you were tempted to put in email #1. Here's a real example that landed a $45k deal: "The reason for my email the other day is because we can book 10 calls on your calendar each month on a pay-per-call basis with personalized cold emails. We recently did this for [Company X], and they closed $25k in their first month. We guarantee a minimum of 10 qualified appointments, or you don't pay. Our average client sees a 3.2x ROI within 60 days. Would you like to discuss this approach for [Company Name]?" Perfect timing? Send your Jab on Tuesday/Wednesday morning, wait 48 hours, then throw your Right Hook if there's no response. Two more follow-ups max after that. Implementation is simple: Take your current first email, bump it to email #2, and write a short, punchy opener for your new first email. Then watch your numbers climb. Speaking of numbers: My traditional approach got a 2% meeting book rate. The 1-2 Punch method gets 8%. That's a 4x improvement simply by reordering and restructuring your emails. Real talk: This strategy works because you're playing the long game. You get two chances to connect before revealing your full pitch, and you're not coming across as desperate in email #1. Btw, what's your go-to cold email strategy?

Your sales emails suck. And guess what? I know because I get 30 of them a day. I see the same mistakes over and over...the boring intros, the endless rambling, and the generic pitches that make my inbox feel like a nightmare. Want to know why? Because your email has 3 seconds to make an impression. THREE. Seconds. That's how long you have before I hit "delete" So if you’re not cutting through the noise, you’re just part of the problem. Here’s why your outreach isn’t working: 🚫 Cut the fluff, now – “Hope you’re doing well” or “Just checking in” is a one-way ticket to the trash. No one has time for that. If you don’t get to the point within the first 5 words, you’re done. ✂️ Get to the point fast – Lengthy emails are a killer. Research shows emails under 50 words see 83% more replies. That means if you're writing a novel, you’re already losing. 📚 Personalize (like actually personalize) – "I see you're in [insert job title here]”—that's not personalization, it’s lazy. Do your homework and show that you understand my specific challenges and goals. If you don’t, I’m clicking delete before you even finish your sentence. 🎯 Relevance matters more than anything – If your email isn’t directly tied to what I’m trying to accomplish, it’s not going to get a reply. I don’t need a generic pitch; I need to know how you can help me solve my problems today. 🔥 Stop the lazy copy-paste – If I can tell you’re sending the same message to 100 people, I’m out. Your outreach should feel like you’re speaking to me, not to the entire world. Personalization isn’t just a buzzword. You’ve got 3 seconds to grab attention and show value. If you’re still using the same tired tactics, you’re wasting your time...and mine. 🎤 🫳 ALSO MASSIVE SHOUTOUT to the folks using video to prospect, can say that personalized video messages get a response from me every time. I LOVE them.

I've run hundreds of email account audits, and I always see the same mistakes. Here are the "5 Deadly Sins" that are killing your email performance – and how to fix them. MISTAKE #1: TOO MUCH EMAIL VOLUME When it comes to email marketing, engagement is far more important than list size. Sending too many emails can overwhelm your subscribers, leading to lower engagement rates, increased unsubscribes, and damage to your sender reputation. This turns into a “boy who cried wolf” scenario, where too much volume results in your messages getting ignored or sent to SPAM. THE FIX: Focus on quality over quantity. Prioritize sending valuable content at a steady cadence rather than hitting an arbitrary volume target. MISTAKE #2: NOT SEGMENTING YOUR AUDIENCE If you’re still sending “email blasts” in 2024, you’re gonna have a bad time. Sending the same email to your entire list without considering a subscriber’s unique needs or interests is a recipe for terrible engagements, sales, and unsubscribe rates. THE FIX: Segment your list based on demographics,interests, or behaviors. Send hyper-personalized content to maximize relevance and improve conversion rates. MISTAKE #3: WEAK OR MISLEADING SUBJECT LINES Using vague, spammy, or clickbaity subject lines is an absolute no-no. If your subject line is unclear, it’s not getting opened. If it makes a promise that your content doesn’t deliver on, your subscribers will lose trust, killing your future engagement metrics. THE FIX: Craft subject lines that are both clear and compelling. Set expectations for what’s inside and make sure the email content follows through on that claim. MISTAKE #4: IGNORING MOBILE OPTIMIZATION Current estimates suggest that around 60% of website visits take place on mobile devices. Similarly, studies have shown that around 40-60% of email opens happen on mobile. So, why do so many brands invest thousands in mobile optimization for their SITE, and almost nothing in optimizing their EMAILS? THE FIX: Use responsive email templates that adjust to any screen size, and always test how your emails look on mobile before sending. MISTAKE #5: FAILING TO ANALYZE PERFORMANCE For many brands, email marketing is an item on a to-do list that just needs checked off. If you’re not running a post-send analysis to determine what’s working and what’s not, you are absolutely leaving money on the table. THE FIX: Analyze your email marketing metrics on a monthly basis to understand what’s working and use that to drive further experimentation and optimization. I see these mistakes in every single account I audit – and it KILLS me. Get these low cost, high impact opportunities dialed in and you’ll dramatically improve your results.