The ingredients lay before you. All chopped up and prepped. Looking gorgeous and fresh. How are you going to make the meal now? What’s the recipe for a great outbound message? Well…that’s where we start today. I’ll be giving you some methods and frameworks on outbound copywriting that take you from rookie to advanced in no time. So, read on. Feel free to take notes. And as always, drop me a line at paul@gassee.com if you have any questions.

Over the past decade, hundreds of founders and startup operators have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the series unfolding in the coming weeks, you will not get only the required frameworks to get you thinking properly about prospecting as a founder. But you’ll get the tools necessary to generate consistent pipeline for your company. So sit tight. Tune in. And, as always, be loud with your questions. Here’s your fourth installment.

Formality kills in outbound copy. And I’m not using the modern slang version of “kills”. No, it murders your outbound copy. Meaning: pronounced dead on arrival in your prospect’s inbox. Before it’s even fully read. The reasons? To start, formality lowers your status in your prospect’s eyes. Your pandering makes you feel inferior to them. Which you want to avoid. In your sales conversations, you want to be the sherpa. The trusted industry expert. The confidant. The person that will guide the prospect through your sales process until the product has been implemented and is delivering value. That role is only possible when your status is a little above that of your prospect. Not coming from below. Addressing your target recipient with a “Dear Sir or Madam” will only start things off on the wrong foot.

The other reason why being overly formal hurts you? It makes the prospect feel like you’re sending them an automated email. Any time we see an overly formal piece of copy, our brains register it as part of an automated effort. The copy hits our retinas, and we’re like, “This message feels so generic and dry. It’s not coming from a human being.” And we press ‘Delete’ or ignore it outright. When you’re less formal, however, and let your personality shine through, we tend to look at the message and ask ourselves, “Could Sophia’s email be one-to-one? As opposed to one-to-many? I could see her writing this herself. Doesn’t feel like AI slop at all.” And when you’ve landed in that camp in your recipient’s mind, you’ve already won. That’s why we tell our clients to write like they would to a friend. Or an internal colleague. Let your individuality show. Your hair down. And allow us to see your quirks. Your idiosyncrasies. Whatever makes you you.

Let’s face it. Even before AI slop was a thing, we were already inundated with dry corporate jargon, business buzzwords and dull copy that made little sense. Anything you can do to stand out will only be to your benefit. So allow folks into the workings of your mind. Let them into your inner world. And reap the benefits of getting more engagement and replies from prospects.

We’ve established the imperative of ridding ourselves of formality. Now, step into this scene of the contemporary workplace, if you could.

Minuscule attention spans. The limited real estate of smartphone screens. And the busy lives of our target prospects. Jake, the Chief Technical Officer at a Series B startup you’d love to sell to, sneaks a look at his iPhone 17 on his lunch break, as he waits in line at his favorite taco truck. He’s coming up for air after wall-to-wall morning meetings, and is finally checking email. Intrigued by your subject line, he clicks on your email. You’ve got a few seconds to capture his attention. With these modern day constraints, it’s no surprise you’ve got to keep your copy super short. Crisp. To the point. With no wasted movement. Zero fluff. Just concentrated essence. Like a morning ristretto. It needs to pack a punch and compel Jake to schedule a quick Zoom call in the coming days.

The point here is: your outbound copy needs to be precise. For a full pitch outbound email, it should be five to eight sentences. Ten at the very most.

And we tend to be long-winded as founders or startup people. We’re proud of our product, that’s been gestating for months. The company we’ve built and its mission. And yet, we must do everything in our power to restrain ourselves. To curb our need to express ourselves fully. We need to find a way to condense what needs to be stated. So as just to elicit the prospect’s curiosity. And invite them to start a conversation with us. Making your copy short is one of the most potent things you can do for your outbound message.

Another powerful action you can take? Pay close attention to your subject lines. And the beginnings and ends of your outbound messages. We tend to focus on the email body copy. Because it feels like the piece de resistance of our communication.

But, in doing so, we forget that our subject lines are pickup lines. You could be the most empathetic, loving partner. But if you’re unable to get the attention of a potential mate sitting across the bar from you, it all doesn’t matter. They won’t be able to experience you as that wonderful person. The same goes for your subject line. You could have the most wonderful email body copy. But without a good subject line that grabs your recipients and entices them to open your email, it’s all for naught. Your email body might as well be blank. One of the bigger topics I coach my clients on is to spend more time on their subject line. Make sure it’s titillating. Curiosity-inducing. That it lures the prospect to click on your email, itching to discover what’s inside. It all leads to more opened and read emails. Which, in the end, gives you a much better chance at more interested replies and booked intro calls.

The beginnings and ends of outbound messages get short shrift but should also be crafted with care. Why is that? Well, because they are often shown in email or LinkedIn messaging clients as “teasers” of the longer message. A good opener in your outbound message will hook your reader. And a good ending will leave them with a lingering impression. If you’re able to make those two bookends crisp and compelling, you’ve got a shot at getting your prospect read on and respond.

Now that we’ve covered the parts of outbound copy that don’t get enough attention and some of the no-no’s when it comes to copywriting, I have a question for you: ever feel stuck when you’re trying to come up with copy?

Well, you’re not alone. It’s a common issue for all of us humans. We stare at our laptops, hands on keyboards, with enough knowledge about our product to make most heads explode. We’ve taken the time to get to know our target market intimately. And we’ve even put together our outbound copy building blocks. And yet, nothing comes out when we’re pressed to produce copy. Like crippling resistance. An intense form of writer’s block. We know we’re got to conjure up something brilliant to catch a prospect’s attention, and we’re all too aware of the constraints at hand. What’s one to do? Well, we’ve got a solution for you.

Rob – our head of outbound & ops – once came up with what we now call the “60-second torture exercise”. Faced with this issue himself, the guy decided to force his creativity by adding another constraint. It might sound counterintuitive, but he was freed by it, believe it or not. It worked so well for him that I was his second guinea pig. I instantly loved this torturous practice so much that we now run all of our clients that want to generate good outbound copy through it. “So, Paul, what’s this torture device you speak of?”, you might ask. Well, it’s dead simple. You pull out a timer. And give yourself exactly 60 seconds to produce the first pass at your outbound email body copy. That’s it! Yes, you’ll get a chance to refine the copy you put down. Perfect it. Take other passes. But the sheer act of adding this time limit allows you to get over yourself. And put that first splatter of paint on the canvas. Freeing yourself from your neuroses. Your self-consciousness. Now, when you do this, it’ll most likely feel like you’ve been thrown in the deep end of the pool. Like it’s an impossible feat. But as time goes on, with more reps, you’ll start to find it manageable. And you’ll produce copy that’s crisp. To the point. Without the fluff that might have been plaguing you in the past. Try it, and as always let us know how it goes.

You now have some method for outbound copywriting. What’s your north star going forward? How do you know if you’re being successful? What to aim for? How to go about improving over time? That’s where we’ll start next week: the metrics you need to track and understand to get better at outbound. And their newfound immense importance to you. Ciao, until next week.