How The Email Subject Line That Made My CEO Cry And Got Me Promoted Transformed My Career

Last Monday, at the ungodly hour of 2:14 in the morning, I found myself staring at my screen, eyes bloodshot from a binge-editing session that had outlasted three cups of coffee and a highly regrettable energy drink. You know, the kind that tastes like a sugar-coated lightning bolt? Anyway, I was in the throes of a personal crisis: How do you get your emails noticed in the avalanche that is the corporate inbox? That’s when inspiration struck, as these things do, in the form of a ridiculous idea: What if I could make my CEO cry with an email subject line? Now, I’m not talking about the tear-jerking, I-just-watched-Marley-and-Me kind of cry. I mean the kind of happy cry that makes someone stand up, look over their cubicle, and shout, "Who wrote this?!" (Or at least I hoped it would be that kind of cry. Worst case, I’d settle for a sniffle.) So, armed with nothing but an absurd goal and the delusional confidence that accompanies a 2 AM creativity high, I set out to craft the perfect subject line. By 3:42 AM, I’d narrowed it down to three contenders—all of which relied heavily on the art of curiosity mixed with a dash of flattery. The winner? “Open for a Smile: A Hidden Gem Just for You.” Cheesy? Absolutely. But also oddly effective. Why did this work? It’s the emotional bait-and-switch. You see, most people go through emails like they’re playing Minesweeper—a quick scan and a steady hand to avoid disasters. When you lead with curiosity and promise something positive, you’re tapping into a powerful human instinct: the irresistible urge to know more, paired with the hope it’s good news. And let’s be honest, my CEO’s inbox wasn’t exactly a treasure trove of uplifting messages. (Mostly budget reports and “urgent” requests marked with varying degrees of panic.) The results were beyond my wildest caffeine-fueled dreams. Not only did my email get opened first thing in the morning, but I also received a company-wide shoutout for “capturing the essence of what our team stands for.” And yes, my CEO did wipe away a tear during the meeting, claiming it was “allergies.” We all knew the truth. That subject line led not only to me getting a handshake with an intensity that could rattle bones, but also a promotion to Chief Writing Alchemist. (No, I didn’t make up that title. But yes, I’m considering getting it printed on a mug.) So how can you bring a bit of this magic into your own email writing? Start with the subject line. Seriously, it’s like the trailer to a movie. If it doesn’t grab you, you’re not sticking around for the full feature. Experiment with curiosity-driven phrases that promise something personal or positive. Your subject line should be the hook that makes even the most mundane email the equivalent of a blockbuster premiere. To get started, imagine your recipient is a jaded email veteran, eyes glazed over from their morning scroll. Craft a subject line that speaks directly to their inner human—not their inner robot. Try something like, “Your Daily Dose of Joy Inside” or “A Small Surprise Awaits You.” Keep it genuine, and if you can, deliver a little joy in the body of the email too. A quick win might be a relevant compliment or a fun fact that’s actually fun. Now, for the pièce de résistance: real results. I tested this strategy on internal memos, client updates, and even the dreaded “we need to talk” email. Open rates skyrocketed from a miserable 15% to an astounding 82%. My favorite achievement? A client who replied, “This is the first time I’ve smiled reading an email. Can we clone you?” (I politely declined, though the thought of an army of Alex clones is oddly appealing, if not a little terrifying.) For those ready to advance to email subject line wizardry, remember this: personalization is your secret weapon. Use names when appropriate, reference specific shared interests or experiences, and always be prepared to deliver on the promise your subject line makes. And don’t be afraid to experiment. A/B test like your career depends on it (because, let’s face it, it might). So, ready to make your inbox a place where people actually want to hang out? Start with the subject line. Transform your emails from digital napkin notes to conversation starters. And if your boss cries happy tears, well, consider it a job well done. Now, go forth and conquer the inbox. Just be sure to share your success stories—I’ll be waiting with a fresh cup of coffee and a notepad, ready to learn from the newest subject line sorcerers.