Why witty email subject lines work better

Why Being Weird in Sales Works (and How I Learned to Love It) Let me share a story that taught me the power of being unapologetically weird in sales. A few years ago, I was trying to land a meeting with a VP who had gone completely silent after an initial call. I’d sent polite follow-ups, clever subject lines, and even a LinkedIn message—but nothing. It was radio silence. Finally, I thought, What do I have to lose? So, I sent this email: Subject: “Are you ghosting me? 👻” Body: “Hi [Name], I’ve got to ask—did I say something wrong? Or are you secretly testing my persistence skills? Either way, I’m not giving up that easily. If this email feels like a bad first date, let’s change the narrative and schedule a quick call instead. No candles or awkward small talk required. Just good conversation. 😉 Let me know! Best, [Your Name]” Within an hour, I had a reply: “This is hilarious. Let’s talk tomorrow.” Why Being Weird Works in Sales Here’s the thing: prospects are bombarded with sales pitches daily. Most emails, voicemails, and LinkedIn messages look like they were written by the same person. If you want to break through the noise, you have to stand out—and being a little weird is often the fastest way to do that. Weird isn’t about being random. It’s about being memorable, authentic, and a little unexpected. The Science Behind Weirdness 1. It’s Disruptive. People skim emails. A quirky subject line or offbeat opener can stop someone mid-scroll. 2. It’s Relatable. Humor or creativity shows you’re human. Prospects buy from people, not pitches. 3. It Builds Connection. Being different sparks curiosity and makes prospects more likely to respond. Weird only works when it’s intentional :) What’s the weirdest thing you ever did to get unghosted 👻 Giulio Segantini

I tested 40 subject lines over 6 months.   Here are the 8 that consistently hit above 60% open rates — and why they work:   'Quick question, [Name]' → Feels personal, low threat 'Saw you're hiring SDRs' → Trigger-based, proves research 'Idea for [Company]' → Curiosity + specificity '[Mutual connection] suggested I reach out' → Social proof 'Your competitor just did something interesting' → FOMO 'Re: [their recent LinkedIn post]' → They wrote it, they'll open it 'Not sure if this fits' → Uncertainty disarms the sales radar '[Name]' → Just their name. Shockingly effective.   What they all have in common: → Under 6 words → No exclamation marks → No 'I' as the first word → Feel like they came from a human, not a campaign   The subject line has one job: Get the open.   It doesn't need to sell anything. That's the email's job.   Which subject line format have you had the most success with? #B2BSales #EmailMarketing #ColdEmailTips #LeadGeneration #SalesStrategy

The subject line's job is never to explain the email. Describe what's inside and you've made the most COMMON mistake in the inbox. The brain has a biological compulsion to close open loops. An unresolved question or a story without an ending physically can't be left alone. Netflix turned that into a business. Every episode ends right when the tension peaks, so stopping feels awful, and the average user watches three to five hours a week because of it. Reed Hastings said their biggest competitor is sleep. Every subject line you write is doing one of two things: 1) Describing what's inside. "Meaningful pendant, up to 40% off." You know exactly what it is before you open it. That works for someone who's been eyeing the product and just needed a reason, and the discount is the reason. 2) Opening a loop the brain has to close. Anti Social Social Club sent a subject line that was one word, "tomorrow." And that was it. You don't know if it's a drop or a limited collab. If you're even a little into the brand, you open it because you can't afford NOT to. The first version tells you exactly what's inside.... while the second makes you open it to find out. Both work, for different people and different moments. But the brands with the highest engagement lean on the second one. They make not opening the email feel like pausing Netflix mid-cliffhanger. The loop comes with one catch: It only works if the email actually closes it. If you open a loop and the email never closes it, people stop trusting your subject lines.

Your brain makes the "open or delete" decision in 500 milliseconds. Faster than a single heartbeat. Half a second. Before you consciously think "Should I open this?" your brain has already run a complete evaluation and made the call. Here's what happens in 500 milliseconds: Stage 1: Pattern Recognition Your brain instantly categorizes every subject line: → Work email (CEO update, team meeting) → To-do item (action required, deadline) → Shopping (order confirmation, sale alert) → Marketing (newsletter, promotion) → Personal (friend, family) The moment the brain files the email into "marketing," it applies a higher skepticism threshold. Subject lines must break the expected pattern within this category without triggering spam signals. Stage 2: Threat/Opportunity Assessment Your amygdala, the brain's threat detection system, evaluates whether this email signals danger or benefit. Generic warnings get ignored. Specific threats or opportunities trigger attention. Stage 3: Relevance The prefrontal cortex asks: "Does this matter to my current goals?" If the subject line doesn't signal direct relevance to the reader's role, situation, or concerns, the brain moves on. Stage 4: Frame Activation Specific language patterns activate conceptual frames that determine how the entire message will be interpreted. Security-focused language activates protective thinking. Achievement-focused language activates competitive thinking. Growth-focused language activates possibility thinking. The frame you activate in the subject line sets the stage for everything that follows. Stage 5: Decision The brain calculates: "Is opening this email worth the brain energy?" And makes the call: open, archive, or delete. What this means for you: Write for clarity first, psychological triggers second. Your subject line should clearly communicate who this is for and what value they'll get by opening. That's non-negotiable. But within that clarity, you can leverage these neurological mechanisms to increase the likelihood that your target audience, the people who will actually take action, decide to open. Break expectations within your category ❌ "Newsletter Marketing Tips #47" ✅ "The WordPress setting that tripled our traffic" Signal concrete consequences or opportunities ❌ "Don't make these email mistakes" ✅ "Is your email signature killing your credibility?" Use role or situation-specific language ❌ "Marketing automation tips" ✅ "CMOs: Your Q4 pipeline problem has a name" Make it instantly clear who this is for and why it matters now. The goal isn't to trick people into opening. The goal is to make it immediately clear to your target audience - the people who will actually click, reply, or convert - that opening this email serves their interests. I'm breaking down subject lines in this week's edition of the EmailOS newsletter. Have you subscribed yet? Subscribe: https://lnkd.in/g9h83HNV

They tested two headlines. One word was different. One ran for 40 years. Over a century ago, a copywriter named Maxwell Sackheim was trying to sell a mail-order English course. He tested headline after headline, and most of them flopped. Then he tried: "Do you make these mistakes in English?" It ran for 40 years. No challenger ever beat it. Here's what's wild. They also tested: "Do you make mistakes in English?" One word different. It failed. The word "these" changed everything. Without it, the reader answers yes or no and moves on. With "these," they have to keep reading to find out what the mistakes are. That one word created a question the reader couldn't answer without reading further. Your subject lines can do the same thing. "Big sale this weekend" tells them everything. Nothing left to wonder about. "We're pulling 3 products from the store on Friday" makes them ask which 3 and why, so they open the email. The difference between a subject line people skip and one people click is the same thing Sackheim figured out a century ago. Give them enough to care. Hold back enough to keep them.

I've been writing copy for 8 years. And I just realized, I use the same 3-ingredient formula in everything. → Subject lines → Hooks → Bullets → CTAs → PS lines Everything. The formula? Benefits, Curiosity, Drama. That's it. Let me show you what I mean. Subject line example: Bad: "New email strategy guide" Better: "The 3-email sequence that brought in $253K (steal it)" → Benefit (brought in $253K) → Curiosity (what's in those 3 emails?) → Drama (steal it = urgency + simplicity) Hook example: Bad: "Email marketing is important for growing your business." Better: "I sent 3 emails nobody asked for. Made $253K. Here's what happened." → Drama (nobody asked for them) → Benefit ($253K) → Curiosity (what happened?) Bullet example: Bad: "Email automation tools" Better: "The one automation most brands ignore (costs them 6 figures)" → Curiosity (what's the one thing?) → Drama (most brands ignore it) → Benefit (saves 6 figures) CTA example: Bad: "Download the guide" Better: "Get the 3-email template that recovered $30K from dead leads" → Benefit ($30K recovered) → Curiosity (how does it work?) → Drama (dead leads = thought they were gone) You don't need all three every time. But the more you layer them, the stronger the pull. I use this in every single piece of copy now. It's become muscle memory. Which of these do you lean on most: benefits, curiosity, or drama? #Copywriting #EmailMarketing #MarketingTips LinkedIn LinkedIn Guide to Creating