Creating head-nod moments in cold emails

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.

Marty’s been fly-fishing 3 months every year for 52 years. This year, he took me with him. Here’s the first thing Marty taught me: “To attract fish, you need to use flies that mimic the bugs in the water.” “These are nymphs.” “Fish are more likely to bite if the fly resembles their natural prey, which right now are these guys.” “It’s called matching the hatch.” In sales, you have to match the hatch too. Your prospects are more likely to “bite” when you match the conversations already happening in their heads. How do you match the conversation? Mine success stories for quotes about what sucked before the customer switched – AKA the “before story.” The key is selecting words within quotes. Extra points if you find emotionally charged words like “nightmare.” For example, here’s a before story quote I found for HEY: “Been using HEY several weeks and no longer dealing with spam, long lists of “unread” messages, or sorting out annoying but important docs” And here’s how I used the before story quote in a cold email: “You shouldn’t have to deal with spam, long lists of ‘unread’ messages, or sorting out annoying but important docs.” The big idea? Good messaging isn’t written; it’s found. Match the hatch.

There's a "C" word I used a lot in my cold emails. I've since stopped. I realized I was often using it in selfish ways: "Curious if you're available next week for a 15 min call." "Curious if you've heard of our company before before." Once I started doing cold email reviews for my workshops, I realized a LOT of us were doing it. So, it became a bit of a nagging, irritating word for buyers to see in a cold email. Now, my philosophy on cold emails is this. A great message sparks curiosity for the prospect to take another look at their beliefs and assumptions about their OWN business, not ours. It's not about being curious if they're free on Tues at 9 am. Or, being curious if they've heard of us. It's about striking a match that lights up their "perceptual curiosity". Perceptual curiosity = the type of curiosity we feel when something surprises us or when something doesn't quite agree with what we know or think we know. Often described as an "itch we need to scratch". The response to feeling perceptual curiosity = we try to find out new information in order to relieve that type of curiosity. Scratching the itch = saying yes to a call, or asking for more information The goal of a cold email isn't to impress them with our case studies, our ROI numbers, or our awards. It's to bring a specific problem POV, loosely held (+ seeking to be corrected), that provokes the prospect to reconsider their beliefs and assumptions about the root cause of the problem, the size of the problem, or the unintentional/under-appreciated negative consequences of current state. In doing so, we give prospects a reason to reconsider how they're solving the problem today. I'm off to the UK tonight to run workshops this week with two companies who want to bring this idea to life in their cold email messages & discovery call motions. Goal = craft a message that gives prospects a valid reason to learn more about the cost of inaction (COI). IMO, a big part of Sales is about understanding basic human psychology. Why? Because humans are pretty predictable creatures. In their personal lives and in their business roles. Excited to be back in the UK with some great GTM teams 🇬🇧 PS - I spelled curiosity incorrectly EVERY SINGLE TIME I USED IT IN THIS POST. Thankful for the red squiggly spellcheck line. Why no love for that "u" in curious? PPS - I'm no expert in psychology (I graduated with a Parks & Rec major, don't laugh...ok, laugh). But, I do think it's an underrated Sales superpower when sellers have a psychology background. PPPS - no fish & chips this time