The Top Misconceptions in Startup Sales, Episode 7
Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the next few months, in the form of weekly episodes, we’ll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you’ll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here’s your seventh installment. Read on.
“I don’t have anything in common with this person. How can you expect me to personalize my message to this prospect?”
“Paul, I can’t relate to him playing competitive volleyball. And being an all-American and MVP.”
“What do you mean? You’ve never played volleyball?”, I replied.
“Well, a little bit in middle school. But that’s about it. I really don’t feel qualified on the topic. And it might feel like a stretch to mention that we have that in common.”
I can’t tell you how many times this issue pops up in my coaching with clients.
Quite a few founders and startup operators feel like they need to have something in common with their prospects in order to personalize at all.
And I’m here to tell you that’s a limiting belief. It sets the bar too high. And it prevents folks from personalizing well. Or even at all.
Now, is it more potent to personalize with a tidbit you have in common with a prospect? Of course. I’d be lying if I said otherwise. Having something in common with the person you’re reaching out to tends to establish an instant kinship. It not only makes the person feel seen. But also says, “Hey, we’re part of the same group. We’re cut from the same cloth. You and I are similar. We should be talking.”
But limiting yourself to things in common will only curb your personalization. Some LinkedIn profiles are very sparse. Some prospects don’t have much of a digital footprint. What you might end up with to pick from might not include anything you perceive as a commonality.
So what do you do then?
Dale Carnegie had our answer, way back when. “You can make more friends in two months by being interested in other people than you can in two years by trying to get other people interested in you.”
Be interesting by being interested.
Remember: with personalization, we’re trying to make the other party feel seen, heard and understood. A deep human desire we all possess. When you make a person feel seen, they feel special. And are compelled to reply to your outbound message.
With good personalization, you aim to increase your reply rates, which in turn has a chance to pull up your interested reply rates.
But none of that says that you need to have anything in common with your prospect. You just need to let your curiosity lead the way. What do you find fascinating about your prospect? What makes them unique? What do you think they’re most proud of?
If you can express genuine interest in those parts of themselves, more often than not, you’re going to unlock a connection with a prospect.
Let’s work with the instance we mentioned above. My client didn’t feel like they had played a sport at a high enough level to comment on it. Or to even relate to it on a deeper level.
I nudged him a bit. “What if you asked him about All-American collegiate volleyball career? And how it contributed to his success in business? Perhaps he picked up lessons that enabled him to really soar…”
“You’re right, I could definitely do that. Let’s write it together.”
We came up with something like this.
Couldn’t help but notice that you had crushed volleyball back in college…what lessons did you pick up during that time that have contributed to your success in business?
We took the liberty to make a link from his starring in a college sport to his outstanding career in business. My client exhaled. He didn’t feel out of his depth. Or that he was speaking out of context. All he did was lead with genuine interest and curiosity.
An additional note on personalization: the more specific you make it, the better. Meaning: the more you get to what makes a person unique, the more they’re going to feel like you understand them.

Let’s imagine for a second that you had spent a few years in your mid twenties in New York City. And that you wanted to reach out to me cold, to sell me your product. In thinking about how you were going to get my attention, you looked up my LinkedIn profile and found out that I too had spent the first couple years of my career in Gotham (not the truth; I was actually in Paris).
You might decide to personalize the beginning of your email to me like this:
Subject Line: hello from a fellow former New Yorker 🗽
Hey Paul,
I noticed you had spent the first couple of years of your career in New York (I also did in my late twenties)…how cool was it to be young in that town? The intensity and liveliness of it was intoxicating to me. I never felt bored.
Now this is what I’d call decent personalization. Just north of mediocre. But far from spectacular. You’re trying to connect with me about living in one of the largest metropolises on the planet. 5 boroughs. A city of more than 8 million people. But it lacks a lot of specificity. I might feel a little anonymous – which interestingly is how people feel in large cities like NYC – if I received this message.
Now compare it with this bit of personalization below.
Subject Line: working out of Williamburg 🍕
Hey Paul,
I saw that you worked out of Billyburg the first couple of years in your career. I happened to be in NYC too (lower Manhattan more specifically) in my late twenties. You ever go to Macolletta? Wasn’t their Margherita pizza just amazing (sauce super fresh, and crust perfectly puffy)?
Now this one above is very good. You’ve gone from talking about a metropolis to the specific neighborhood (Williamburgh) within a borough (Brooklyn). You even zero’d in on a great pizza joint I may have gone to. Or heard of. You’re using NYC jargon – “Billyburgh” – to identify Williamsburg. Finally, you blended our commonality of being former New Yorkers, with genuine interest in my unique experience within a smaller subsection of Gotham.
Feel the difference?
Good. Now get out there and personalize to your little heart’s content.
Remember: there’s no need to have anything in common with your prospect. All you need is genuine interest and curiosity. And an ability to verbalize it.
Next week, we’ll discuss that, while tempting, low-hanging fruit is not the most important thing to focus on in your go-to-market.