1 Myth, 1 Home Run & 1 Lesson

Myth: When writing outbound copy, being formal or professional is helpful.

We’ve all seen them: stiff emails dressed up with ‘formal’ or ‘professional’ words. We reach for the Delete button before we’ve finished reading the entire subject line.

Here are some examples:

“Introducing [BrandName]”

“[BrandName] will solve [YourProblem]”

“[BrandName] is part of Gartner’s Magic Quadrant”

There’s two reasons these emails don’t work: they feel like sales pitches, and they look like every other sales email clogging up your inbox.

Professionalism is important in business, but ironically the best, most successful sales emails are personal and informal. They’re crafted to feel catchy and elicit your curiosity.

Here are example subject lines:

“how are you solving [YourProblem], [FirstName]”

“you alive, [FirstName]?”

“feeling like Tom Cruise yet, [FirstName]?”

These spell out your first name, which naturally captures your attention (and is more than can be said for 90% of cold emails).

The same rules apply for the email body. Write as if you’re dashing off a note to a close friend. Let your personality out. Include humor. Don’t hesitate to write sentences all in lowercase. This is an opportunity for you to loosen up that necktie and put on your loafers.

Here’s one I wrote wearing my weekend shoes:

Hey [FirstName] — how’s normal life Post-COVID? For me…it’s been exhausting interacting with friends more…I’m sure that’ll pass soon. I used to think I was an extrovert haha…

Speaking of exhaustion…how’s your accounting team performing? This time of year work is a little hectic and productivity is under a microscope. People like you keep telling us they’re not getting enough from their existing headcount. 

We’ve built software that organizes your accountants’ work and allows them to be a lot more efficient…36% on average. Disney, Coca-Cola, and BCG are among the teams that already use us. 

How about a quick call early next week to see if there’s a fit? All it’d take is 10-15mins. How does Tuesday afternoon look to you…?

Let me know…would love to connect!

Take care,


Now…how did that feel? Quite a bit more personal right? It could even pass for an email that’s not automated. And yet that’s the key to success in automation. You want to industrialize your process, all while your touch points feel personalized. Be as colloquial and as casual as possible.

At the end of the day, prospects want to buy from a human being, not a faceless corporation. To see your reply rate increase, write like you would to a friend, and let your humanity shine through.

Home run:  Last year, while many companies were spinning their wheels figuring out how to survive, my client 3x’ed their MRR in 12 weeks.

A trends startup approached me late Q1 last year with a major problem. They were getting a ton of inbound interest — including from household names — but very little was converting to actual sales. The founder pair had garnered a ton of attention through PR, content and thought leadership, but next to nothing was hitting their bottom line. Recognizable brands said they wanted their product, but traction was minimal. The few deals they were able to land were far too small. The founding team wondered if they were ever going to hit product market fit, as they had been floundering on the sales front for over a year. Their runway was limited. So, they needed to get to ramen profitability before time ran out. One co-founder told me, “We need to make more money…for the survival of the company.” To make matters thornier, the pandemic slammed into us as we started our engagement. Would our customers suffer from budgetary contractions? Would fear play a role in their buying process?

As I stared into their sales funnel, I spotted major leaks. Folks were initially interested in the platform but weren’t jumping on a call with us. They came to the site and signed up for access to the platform, but somehow didn’t want to talk to us. We had little shot at making the sale as things stood. Once prospects did join us on the initial call, most of them didn’t stay in our sales funnel. Free trials were not converting to paying customers. We needed to patch things up. And quickly.

What could we use as a lure for that first call? I wanted something that would compel them to attend. Without much delay, we came up with a consultation session. That first call was not only an introduction to the platform, but also a consultation where the salesperson delivered trends and insights. The prospect left that first meeting not only intrigued but wowed by the understandings they had gotten. They could walk into their next team meeting and flex their newfound industry knowledge, “Did you know that we’re seeing increased demand in [product category]? A 37% increase in North America over the next 2 months, as a matter of fact.”

Before ending our first sales meeting, we promised them even more on our next call: we’d help them answer some of their company’s major strategic questions. This second call was about unveiling the platform tailored to their needs. It was also about us getting them started on their credit card activated free trial. And setting them up for success for that initial stretch and beyond.

Once changes were in place, our two punctures were plugged and our sales process started humming. All of a sudden, our steady flow of inbound leads now turning into greenbacks, and we were off to the races.

The biggest lesson here is this: we transformed the customer experience. Offering demos to folks that had been curious about our data product wasn’t enough to get leads to convert. No prospect wants to sit through yet another product demo. Delivering personalized, actionable insights on a silver platter was the key to having them make their way down our sales funnel. And ultimately to a closed deal.

Lesson: The selling part is easy. It’s the “not selling” part that’s hard.

This gem was uttered by my coach several months back, in the context of selling my sales coaching services. It stuck with me ever since. Here’s what he meant. We all know the major selling points of our product or service. At a basic level, we know how to articulate those value props, and even handle major objections. And once we have some sort of sales process in place, we know how to lead the prospect through it, and get the deal across the goal line.



What’s much harder is to recognize what’s happening in our prospect and pull back at the appropriate times. Sales is about recognizing when to pour it on, when to sprinkle in a pinch of selling and when to not sell at all. Just like a good sauce, it must taste just right. A top-level Chef will intuitively know when to make the necessary adjustments to her dish. She’ll keep tasting things, tunes into her senses, and steps in with a pinch of salt at exactly the right time amidst the madness of her kitchen. Sales works the same way. Despite the many things going on around you, the feelings you’re managing on both ends, you need to be acutely tuned into your prospect. You might ask yourself the following questions, “Are they already sold?” “Are they ready to move on to the next step?” If you’re getting resounding “Yes’s”, then it’s time to move things along.

The last thing you want to do is keep selling when the prospect is either already sold, or is selling themselves. If the deal is already closed, you want to discuss next steps; which typically include things like payment, contract, and onboarding. If the prospect is selling themselves, you want to get out of the way. Few forces are as strong in sales (or otherwise) as someone convincing themselves of something. In those cases, you want to let them do the work for you. Adding in anything at that stage is only intruding on their cognitive journey. You risk derailing them. That’s when you want to let them talk and work their way through to a closed deal.

That doesn’t mean prospects won’t get to a point where they need a little nudge from you. They might even run into Everest-sized objections that you’ll get them over. But, the key here is to recognize when you need to intervene and when you can let the prospect close themselves. The ability to recognize when not to sell and actually shut up is an advanced form of sales.

Which leads us to the counterexample: a terrible sales experience. Most of us have felt the pain of a salesperson not being in-tune with their environment. They fail to understand what’s happening in front of them. They keep pushing something that doesn’t need to be pushed. You might already be convinced that you need their product, but they haven’t switched off their sales pitch. They lean in and insist, “You should really consider our solution for the issues you’re facing.” And you think to yourself, “I’ve been giving you buying signals that I want this thing for the past thirty minutes. Let’s move on already!” Depending on the prospect’s patience, the salesman’s tone deafness could end up costing him the sale. Had he known that his sales sauce tasted delicious, he might have left the dish alone, and been on the way to closing a deal.

So next time you’re selling, keep your antenna up. Track your prospect. Taste the sauce. What are they telling you? Are they sold already? Can you move on? If so, it’s time to use restraint. Adding in more selling would only ruin the dish. And the deal.