The Biggest Outbound Sales Mistakes Founders Make, Episode 6


We tend to think that our email body copy is the most important thing we’ll be writing. 

But you could send a blank email if it’s left unopened by your prospect. 

Your subject line is your pickup line. If you don’t elicit curiosity and have your prospect click on the email, there’s no need to spend time writing the body itself. 

The same goes for the first and last few lines of your email. If you don’t write something attention-grabbing and compelling, your prospect might open the email, start reading it (or skim down to the call to action), and press “Delete” before giving it a second thought.


In the last 8 years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. I’ve done my best to help. And in doing so, I’ve spotted patterns: those costly outbound sales mistakes that keep occurring, and that prevent startups from growing to their full potential. Over 10 weeks, we’ll examine each of these very closely: at the pace of one per week. Consider this your mini-series on the biggest outbound sales follies founders make. And here’s your 6th installment. Read on.

Founders don’t devote enough attention to their subject lines and the beginning (or end) of their outbound messages.

Paying close attention to what you write early and late in your messages will do you good. Put yourself in your prospect’s shoes. 

What would intrigue or titillate them? What would get them to read on? 

Those are the questions you should be asking yourself as you write your subject lines and email body copy. A quick example to illustrate this: when coaching our clients, we tell them to never capitalize any of the words in their subject lines. Something as minute as that changes the way the prospect interacts with the subject line. Instantly, the message feels personal. And your brain can’t reconcile it coming from a marketing automation tool. “It must have been penned by an actual human being, sitting behind their typewriter, thinking of me exclusively.” Well…part of that might be wishful thinking…but a prospect can dream.  

If you take your craftsmanship seriously, you might come up with subject lines that are similar to some of our favorites. “quick question” is a classic, as it tends to feel like something you’d write to a friend or acquaintance. And who doesn’t get curious about a question being directed at you? We are trained from a young age to answer questions that are asked of us. Why would that change in this email medium? 

Another fun one that works well is “how’s Croatia?” This one we’ll tend to use as the subject line for a breakup email. That email asks the prospect if they’re enjoying Croatia from the top deck of their megayacht as they’re sipping on Dom Perignon and being fed caviar. It paints a surreal picture of them without a care in the world because they’ve completely solved all the problems they have ever faced in their professional lives. As they’re most likely not on the Mediterranean on a large boat, they have to ask themselves, “What am I missing? Why don’t I jump on the phone with Matt so he can help me solve some of my issues?” What started it all, however, is the catchy subject line. If you’ve never been to Croatia, or are not there at the moment, you’re going to be asking yourself why you’d receive such an email, and will likely click on it out of curiosity.   

Lastly, any time you can include your prospect’s first name in a subject line, it’s a good thing. We’ve been trained to respond to our name since shortly after birth. We can leverage that instinct by making sure we call upon the prospect in subject lines like “quick question, [FirstName]” or “feedback from you, [FirstName]?”. 

An advanced tip for you: In an outbound LinkedIn message, your recipient will be able to not only see your message’s subject line but also the first 5 to 8 words. The more alluring these are, but more likely you are to engage them in a conversation. Make sure you make those lines snappy and differentiated from anything else they might receive from LinkedIn messages. Here are some examples:


Hey Marc, I sent you a couple emails about sales consulting. Did you see them? 


Hey Marc, I went to USC, graduated 2005. Would be great to connect with an alum. BTW also saw you know Peter Smith – he’s a good friend!

In each instance, the first bit of the message has a high probability of tickling your prospect’s brain. The first one mentions emails that have been sent. It’s likely to elicit a little FOMO. Who wants to miss an important email? The second LinkedIn message makes sure to point out two things the rep and the prospect have in common – going to USC, and having Peter Smith as a connection. It’s hard to ignore someone who went to your alma mater. And if Peter Smith is also a close friend, it’s almost impossible to imagine the prospect wouldn’t respond to this message if they see it.


In the New Year, we’ll go over something founders do out of haste but ends up hurting their chances of engaging with their target persona.