How to Keep Sales Emails Relational and Human

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.

“Hey there! I see you work in performance marketing…” If you’ve ever rolled your eyes at outreach like this… you’re not alone. In today’s age of AI-powered tools and data, generic messages are starting to feel lazy. Especially in B2B, where your audience is informed, busy, and expects relevance. Here’s what I believe: When you reach out to someone with no mention of their name, their role, their post, or a shared context, you’re signalling, “I couldn’t be bothered doing a little research.” And if I’m a decision-maker or an influencer in your target account, you just lost your chance to build a meaningful connection. 📊 Consider this: about 80% of B2B buyers expect personalised interactions from their vendors. If you skip that step, you’re not just missing a best practice; you’re mismatching expectations. So what does truly personalised outreach look like? “Hi Vineeta, I loved your recent article on Black Friday campaigns. It made me think…” “We met briefly at [Event] you mentioned scaling tech hubs in Bangalore; wanted to share…” “Noticed your role as Marketing Lead at [Company], we’ve seen similar firms cut vendor onboarding time by 40%…” If you treat the inbox like a hopper for mass messages, you end up in the “delete” or “ignore” pile. If you treat it like a doorway to a conversation, a human one, you start relationships. You earn trust. And that builds pipelines. Here’s the reality for marketing & sales leaders: 🔹 Our job isn’t to send one-size-fits-all outreach. 🔹 Our job is to engage humans, professionals who appreciate relevance. 🔹 In the AI era, automation should enable personalisation, not replace it. 🔹 Lazy outreach isn’t clever. Thoughtful outreach is. So if your inbox is full of “Hey there” messages, remember: you’re not just a name on a list. And if you’re the one sending them, it’s time to do better. To all marketers, sales pros & growth leaders: if you call yourself someone who drives revenue, start with respect for whom you’re talking to. #B2BMarketing #Sales #Personalisation #ABM #Growth #MarketingLeadership

Most people send a plain text email after a great sales call. I send a video. The screenshot below is a real follow-up I sent after a prospect meeting. Instead of just recapping in writing, I recorded a 2-minute Loom video sharing what I learned, what I’m envisioning for their event, and why I’m genuinely excited to work together. In today’s world of noise and automation, a video like this is a humanizer. It gives them something to feel, not just something to read, and it gives them a powerful tool to forward to their internal decision-makers. The psychology behind this is fascinating. When someone sees your face and hears your voice, it activates the mirror neuron system in their brain, essentially helping them feel emotionally connected to you, as if they’re in the same room. That’s empathy. That’s trust. And trust is what drives decisions. Research shows that only 7% of communication is verbal; the rest is tone, facial expression, and body language. In a sales process full of text and data, the human brain craves the richness of video. It’s also about cognitive ease. According to research from Princeton and the University of Michigan, people are more likely to trust and act on information that feels easy to process. A clear, engaging video makes your message stickier. Add a little story, a little emotion, a little spark, and suddenly you’re not just another vendor in the inbox. You’re a trusted voice. Taking the time to send a video builds social capital. It says, “I care.” It says, “This mattered to me.” That emotional generosity has ripple effects in a referral-driven business. So if you’re trying to stand out, build relationships, and grow your business, try adding a short, heartfelt Loom video to your follow-ups. Whether it’s a cold prospect, a warm lead, or a longtime client, your energy is your edge. Presence beats polish every time. Link to how to use Loom is in the comments. Happy Monday ya'll, let's go scale our impact.

Cold emails don’t have to feel cold. When you master tonality, each email becomes a conversation that resonates with your prospect. Here’s how you can strategically shift tone to create emails that build trust, uncover insights, and drive action: 1. Curious Tone: Start your outreach with curiosity. It’s a subtle way to show genuine interest in your prospect’s needs. By asking questions about their challenges or industry, you encourage a reply that opens the door for deeper dialogue. "How are you tackling X challenge?" feels far more engaging than a direct pitch. 2. Challenging Tone: Perfect for prospects who may be hesitant or stuck in decision-making. This tone nudges them to consider the cost of inaction, positioning you as the solution. Use it to highlight what they might be overlooking, but avoid sounding confrontational. A line like, "What happens if X challenge goes unaddressed?" can create a sense of urgency without pushing too hard. 3. Concerned Tone: This tone works wonders when addressing objections or discussing pain points. It conveys empathy and builds rapport, making you sound like a trusted advisor rather than just another salesperson. For example, "I’ve noticed many businesses in your industry are struggling with X; it’s a challenge that shouldn’t be underestimated." 4. Playful Tone: Ideal for sparking connection. A touch of humor or lightness can make your email stand out, especially in a crowded inbox. This tone is best used sparingly and works in less formal industries. A playful P.S. like, "I promise no hard pitch — just seeing if we’re on the same page!" can keep the conversation approachable. 5. Confused Tone: This is a subtle yet powerful approach that encourages prospects to elaborate on their challenges. By “not fully understanding” an aspect of their industry or company, you prompt them to explain — often revealing deeper insights. A line like, "I’m trying to wrap my head around X; am I missing something here?" signals curiosity and shows you’re listening. 6. Multi-Tonal Approach: The real art of tonality comes when you mix these tones across your emails. For instance, start curious, then shift to concerned or challenging based on their reply. It’s all about keeping the conversation natural and engaging — just as you would in person. --- Craft each email with intention, and let your tone drive the conversation toward connection. In cold email outreach, a well-chosen tone makes all the difference between an ignored message and a conversation starter. #ColdEmailTips #SalesStrategy #Tonality

Email personalization isn’t just about adding ‘Hey [First Name]’ and calling it a day 🙄 If you want to stand out in a sea of bland, forgettable emails, you’ve got to go deeper. → I’m talking about crafting emails that make people feel seen. → Emails that actually connect with your audience and feel like a conversation - not a sales pitch. 🌶️ Here’s the deal: Personalization is about RELATABILITY. It's about knowing your audience so well that your email feels like it was written just for them, not some generic template. So, what does that actually look like? ⚡️ Share behind-the-scenes content - like how your products are made or a day in the life at your brand. Let them feel like they’re in on something. ⚡️ Send curated recommendations based on their purchase history. Not just “You bought this, so you might like this,” but more like “You’ve got great taste in [product category], here’s a vibe we think you’ll love.” ⚡️ Celebrate their milestones - birthdays, anniversaries, or even the day they joined your community. Make them feel special. ⚡️ Tap into shared values. If your brand cares about sustainability, empowerment, or community, weave that into your storytelling. Relatability is about connecting on a deeper level, not just selling a product. The bottom line? An email that feels human is an email that converts. Build trust, spark a connection, and let your brand’s personality shine through 💌 #personalizedmessaging #customerengagement #emailmarketing #DTC

10/10 Sales emails fail before the offer even shows up When people open an email, they can instantly sense whether it was written by a human or assembled like a document The moment it feels formal, heavy, or over-structured, the reader mentally checks out. They may not unsubscribe it immediately, but they stop engaging with it. That usually happens because the email was written directly inside the email tool. When you open Gmail or Outlook, your brain switches into “professional writing” mode. You over-explain You add filler lines You sound like a company, not a person The result: Clean grammar. 0 emotion. Low replies. Now try this instead. Write the message as if you’re texting someone you respect but don’t know well. Short lines. Natural pauses. One thought at a time. Look at what happens when you write the same message in iMessage, WhatsApp, or Notes first. You remove corporate tone automatically You keep sentences tight You sound human, not scripted That shift alone changes the entire feel of the message. This is why replies increase. People do not reply to emails. They reply to messages that feel like they were written for them. A simple way to apply this in daily outbound work is to treat every email like a text conversation that just happens to be sent via email. Write the message in a notes app first.  Read it once slowly. If it sounds like something you would genuinely send to a person, keep it. If it sounds like something you would never say out loud, rewrite it

One of the greatest opportunities I see for the next generation of client-facing professionals: Being the ones who can read and exercise the norms, whether with colleagues or clients, and still infuse their own personality into the work. Those who can master this will be the ones who build stronger relationships and ultimately win more business. Sure, the pendulum has swung hard toward AI efficiency. And proficiency in it will likely be an essential skill. But over-relying on it? That comes with a hidden cost: it can dull the skills of empathy, discernment, and human connection. I suspect it might become tempting to believe that the safest path to employment and promotion is to keep your head down in automation:  Follow the prompt exactly, never straying from the template, and assume that originality is too risky. But customers can feel when you’ve disappeared behind automation… and it seems that they don’t love it. According to Salesforce, 52% of customers say they’re willing to pay more for a great customer experience, and they define that experience as one that feels more personal and less automated. That means the professionals who keep showing up with genuine connection won’t just feel different (in a good way!), they’ll be the ones winning more trust and more business. This humanness will be the differentiator. Some easy ways to practice this is to start by noticing the social norms, and then thoughtfully adding personality to them. Like: ☑️ Pay attention to how experienced colleagues communicate with clients. What tone do they use in emails, how do they open conversations, how do they handle pushback? How can you use that as a framework and then infuse your personality into it? ☑️ Notice how client meetings start. Do they jump right into business, or spend a few minutes building rapport? What do you know about the client that you can chat about beyond asking about the weather :)  ☑️ When you send a recap or follow-up, include a warm line or a small personal detail you remembered, instead of relying solely on a template. Because if more than half of your customers are willing to pay more for an experience that feels human, it’s a skill worth exercising to make sure they get it! #YouthSkills

Your prospects don’t need another “Hope you’re doing well” in their inbox. And they definitely don’t need another “Just following up…” If your outreach sounds like everyone else’s, it gets ignored. Every salesperson is saying the same thing. Every inbox is flooded with weak, low-effort messages. If you want a response, you need to stand out. Here’s what you should STOP saying: "I’d love to connect!" → No one connects for the sake of connecting. "Are you the right person for this?" → Lazy research kills deals. "Let me know if you’re interested." → Your job is to create interest, not wait for it. Instead, say something worth replying to. Open with relevance: “I saw your post on [topic], and…” Make it about them: “Curious—how are you handling [pain point]?” Challenge their thinking: “Why are you doing [X] this way, when you could do [Y] instead?” Provide value upfront: “We found [insight] works best for [pain point]. Thought you’d find it useful.” The best messages feel natural. They read like something you’d send to a colleague. No fluff.  No filler.  No corporate nonsense. Fix your outreach, and you’ll fix your response rates. Share this with your team if they’re still sending bad messages.

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.

You know how most cold emails feel....off? I think there's ONE big cause behind this. Companies fall in love with a value proposition - it's great when the founder uses it to describe their company to friends, investors, media, etc... ...so they hand it off to a rep. "Go write a cold email!" The problem is that a value prop is a (very) high-level summary of what the company does. A sales conversation needs to be the opposite. ❌ high-level ✅ super specific ❌ about the company ✅ about the customer So while value props are great for internal direction and quick intros with strangers, they're not good for connecting with prospects. This sets the sales rep up for failure. Of course the email sounds general, impersonal, vague, etc. Instead, try using the job story framework. It comes from the Jobs to be Done (JTBD) methodology, and it looks like this: When [SITUATION]... I want to [MOTIVATION]... So that [DESIRED OUTCOME]. Unlike most value props, a job story is written from the perspective of the customer. I've been a JTBD practitioner for about 7 years (thanks Val Geisler for setting me on that path). It's a game changer for customer research and copywriting. I use job stories these days when training sales reps to write more human, more natural, and ultimately more effective emails. A good job story can totally transform the direction of your emails....and you can create many, many different stories. Here's the prompt (btw it does something secret that I didn't mention in the carousel below....but I'll talk about it tomorrow and show you how to isolate the BEST job stories): ------------------------- ------------------------- "Imagine a B2B SaaS company [Company Name] with the following value proposition and target audience: Value Proposition: [Describe the key service or product offering and its primary benefits.] Target Audience: [Define the specific group of businesses or professionals the company aims to serve.] Based on this, create five job stories for the company, focusing on how its product or service addresses specific scenarios and needs of the target audience. Each job story should follow this format: 'When [specific situation or challenge faced by the target audience], I want to [what they want to achieve or the action they want to take], so that I can [desired outcome or benefit].' After creating the job stories, evaluate and rank them based on their impact and relevance to the target audience. Explain your reasoning for the ranking, focusing on factors such as the universality of the need, potential impact on the customer's business, and the emotional resonance of the story. End your response by summarizing how these job stories collectively showcase the value of [Company Name] to its target audience." ------------------------- ------------------------- Special shoutout to Katelyn Bourgoin and Neal O'Grady 🍉 for bringing up job stories in the last Un-Ignorable cohort. If you use this, let me know!