How to Build Authentic Connections with Cold Emailing

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 used to send >250 custom outbound emails every week. Yesterday, I was introduced to someone who remembered one of those emails from literally 10 years ago. Here's my outbound strategy for anyone that wants to master cold outreach: 1️⃣ do not sell yourself at the open >> seriously, stop talking about yourself. no one cares about you << Instead: just say who you are, and move on to talk about them. 2️⃣ tell people why they are great - I liked to make a list of at least 5 points - I would write custom points for each recipient - I wrote simply and directly - Inspired by Dale Carnegie - people like to be liked 3️⃣ sell the CONVERSATION, not the opportunity - I never pushed people into existential consideration - I only asked them for 15 minutes, they could spare it - I NEVER sold the role or company, I'd only give them 1 sentence about it 4️⃣ be very direct - I always told people "I think you could be a fit for a job here" - But... I never said the specific job, or qualified it further - People need to know what you want, but they don't need all the details 5️⃣ use humor - I've meme'd since the dawn of my professional time - It seemed to work, lots of people just wanted to respond - Them responding = opening to get them on a call 6️⃣ be fast + use tools - you need to move fast to get 50 good messages out per day - I used a template to populate my open + add bullet points (but not content) - I used TextExpander to insert saved "custom" points. If I'd already written to a musician and explained why I thought their background in music made them an interesting prospect for an engineering role, I'd save that exact verbiage and re-insert it with TextExpander in future messages. - I use all the gmail hotkeys, it helps give you little bits of advantage on a process you will repeat tens or hundreds of thousands of times - it's worth getting gud -------------------------------------- That's it. Remember that people like being liked. Remember that no one cares about you. Remember not to force people to think too far ahead. Oh... and remember that 90% of the time, it won't be the right time, and that's just the process of finding the 10% who are ready to talk.

I just watched a sales rep spend 3 hours crafting the "perfect" LinkedIn message to a prospect who bought from his competitor yesterday The prospect had been posting about their challenges for 6 weeks. Sharing articles about the exact problem this rep's solution solves. Commenting on industry discussions about implementation timelines. But this rep never engaged with any of it. Instead, he was busy perfecting his cold outreach template while his competitor was building relationships in plain sight. This is social selling backwards. Most sales teams treat LinkedIn like an email database with better targeting. They research profiles → craft personalized messages → send connection requests → pitch immediately But social selling isn't about better cold outreach. It's about becoming part of your prospect's decision-making process before they even know they're buying… and just keeping it casual, like a normal human. Here's what the highest-performing social sellers actually do: → They follow prospects months before reaching out → They add value to conversations prospects are already having → They become a trusted voice in their prospect's content feed → They earn permission to have sales conversations When you consistently add insight to someone's posts for 4-6 weeks, your eventual outreach isn't cold anymore. It's the natural next step in an existing relationship. Your prospects are literally telling you their priorities, challenges, and timeline through their LinkedIn activity. Stop treating social selling like fancy cold calling and start treating it like relationship building at scale. How much of your prospect research happens on LinkedIn versus actually engaging with their content? — Enjoy this? 📱 Join our community: https://lnkd.in/e3WAJnft

𝗠𝘆 𝟱-𝗦𝘁𝗲𝗽 𝗟𝗶𝗻𝗸𝗲𝗱𝗜𝗻 𝗢𝘂𝘁𝗿𝗲𝗮𝗰𝗵 𝗙𝗹𝗼𝘄 (𝘁𝗵𝗮𝘁 𝗰𝗼𝗻𝘀𝗶𝘀𝘁𝗲𝗻𝘁𝗹𝘆 𝗴𝗲𝘁𝘀 𝗿𝗲𝗽𝗹𝗶𝗲𝘀) Most salespeople treat LinkedIn outreach like a cold email mass blast or a generic pitch and pray for replies. No wonder most messages get ignored. Over the past 20 years in sales (and after helping hundreds of sellers), I’ve built a simple 5-step outreach flow that actually starts conversations instead of killing them: 𝗦𝘁𝗲𝗽 𝟭 – 𝗖𝗼𝗻𝗻𝗲𝗰𝘁 𝘄𝗶𝘁𝗵 𝗰𝗼𝗻𝘁𝗲𝘅𝘁. Don’t just hit “connect.” Personalize your request with relevance. Show you know who they are and why connecting makes sense. 𝗦𝘁𝗲𝗽 𝟮 – 𝗥𝗲𝗳𝗿𝗮𝗺𝗲 𝘄𝗶𝘁𝗵 𝗶𝗻𝘀𝗶𝗴𝗵𝘁. Instead of pitching, share a short, valuable observation about their role/industry. Position yourself as someone who brings perspective—not pressure. 𝗦𝘁𝗲𝗽 𝟯 – 𝗘𝗻𝗴𝗮𝗴𝗲 𝘄𝗶𝘁𝗵 𝗮 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻. Ask something that sparks dialogue (not a yes/no dead end). The goal is to open the door, not close the deal. 𝗦𝘁𝗲𝗽 𝟰 – 𝗔𝘀𝗸, 𝗱𝗼𝗻’𝘁 𝗮𝘀𝘀𝘂𝗺𝗲. When the timing feels right, ask permission to share how you help—don’t force it. Respect earns replies. 𝗦𝘁𝗲𝗽 𝟱 – 𝗧𝗲𝗹𝗹 𝗮 𝘀𝗵𝗼𝗿𝘁 𝘀𝘁𝗼𝗿𝘆. Stories beat stats. Share a quick example of how you’ve helped someone like them solve a similar problem. Relatability builds trust. 👉 Put all 5 together, and you’ve got a natural, non-pushy flow that feels more like a conversation than a pitch. I'm curious, which of these 5 steps do you feel 𝘺𝘰𝘶 𝘯𝘦𝘦𝘥 most in your outreach right now? Drop it in the comments and I’ll share some message templates with anyone who chimes in.

Raise your hand if cold emailing someone actually makes you sweat 😓 I get it — cold emailing can feel incredibly daunting, but it doesn't have to be. As someone who has "shot her shot" many times over InMail, DMs, emails, etc. there's a few tips I have on how you can (as my amazing co-host Gianna Prudente says) make the cold email a little warm: 1. First, remember there's still another person on the other end. Behind every inbox is a human being with their own goals, challenges, and experiences. Approach your email with that in mind. Instead of diving straight into a request, take a moment to acknowledge their work, share why you admire it, or highlight something you have in common. BE PERSONABLE, Y'ALL. 2. Balance professionalism with personality. Yes, you want to sound polished, but don’t be afraid to let your personality shine! Authenticity goes a long way. Share why you’re reaching out, what you hope to learn, and how you see this connection being valuable for both of you—not just you. I also do believe in courtesy: When you reach out, say "good morning" or "hello". Don't just jump into the ask. 3. Focus on building community. Networking isn’t a one-way street. The strongest relationships are built on mutual value and not feeling like you're being taken advantage of. Instead of making it feel transactional (“Can you do this for me?”), think about how you can contribute to the conversation or be helpful in return. You’ll go farther by fostering relationships over time rather than expecting quick wins. Remember: the goal isn’t just to make a connection—it’s to build a relationship. Let me know in the comments below what some of your favorite networking tips are, and be sure to check out the latest episode of "Let's Talk Offline" (and be sure to follow the show!) where Gianna and I hang out with our work bestie, Morgan Young all on building your network and getting more comfortable with building your community.