When I first moved back to the United States after living in post-revolutionary Egypt while I did economic development work, I decided to give online dating a try.

Within a day of setting up my OK Cupid account, there were dozens of lazy and creepy messages from desperate guys.

There were a handful of really nice and thoughtful guys I went on dates with too, though.

After a few weeks, I started to realize the parallel between online dating and sales.

The guys with the best approaches had similar strategies and "game" to some of the best salespeople, while the worst messages reminded me of really bad spammy cold emails I had received before.  

This is what my online dating experience taught me about sales:

#1. Writing Thoughtful and Original Messages Usually Wins

Just like some people are more attractive than others, some products and services are also more naturally appealing to buyers than others. How "unsexy" or "sexy" a product or service is will determine how easy or hard it is for the salesperson to sell it.

However, the best "inside" (remote) salespeople are the ones who can craft thoughtful messages that stand out in our inboxes and our minds.

Whether you're online dating or trying to decide on which vendor to buy a product from, you won't pay much attention to the 50 messages that look and sound identical because you're overwhelmed and can't easily differentiate them. That's why copying cheap tactics that everyone else's using doesn't work very well, since everyone else is already using them.

Instead, you want to be the person who writes something that sounds original and unique.

Ideally, that message should focus on something that would appeal to the person you're messaging, rather than everything about you or your company.

#2. Don't Be a Narcissist, Or You Will Turn People Off

No one wants to read a long from a narcissist: not in sales, not in dating.

Whether you're dating someone or in sales, you won't have much luck if you make everything about you. No matter how incredible you or your product may be, people don't want to hear someone talk about themselves all day.

They don't care.

What they really want is to have a conversation, and have someone listen to them. When you show you want to learn more about someone by asking them questions this signals that you actually care about them. It shows them that you want to learn more about them, instead of just being in love with yourself.

So no matter how amazing you are, try to make the conversation, whether offline or online, about them, instead of you or your company.

#3. Be Persistent, But Not Creepy

Persistence is part of the secret to being successful in both dating and sales.

You can't give up too easily, or you'll lose out on great opportunities that might have come to fruition if you just kept trying.

You never know when it might just not be the right timing for someone, or if they have objections or deal breakers you might not have appropriately addressed. If you keep trying you might be able to overcome those hurdles; or you might not, but you'll never know if you don't try.

But there's a difference between being persistent and being creepy and obnoxious.

I often see salespeople writing cold emails and cold calling when it's clear that someone is absolutely not interested. I realize that many salespeople are still evaluated on metrics like "calls dialed" or "emails sent," which is a big part of the problem and not their fault. However, "just following up" with people for the sake of following up, without empathy or strategy, is incredibly annoying and very ineffective.

So if you're going to be persistent, try to have empathy and pay attention to the signals the buyer (or your date) is giving.

Have they indicated any sort of interest in your product (or you)?

If they aren't responding to you, why might that be?

What else new can you say or try that you haven't done already so that you're not just being obnoxious, repetitive and redundant?

The more you think about them and less about you, the more successful you'll be.

#4. Keep Testing Different Things Until You Figure Out What Works For You

No two buyers are identical, and no two women are either.

Just as different men have varying tastes in what kind of women they like, as well as what approaches will work for them, companies need different sales pitches because their products and services are different and they might be selling to a different audience.

That's why it's important that you try different things to see what works for you.

My favorite dates and messages from guys on OKCupid were the ones that were thoughtful and original that had creative and interesting ideas for dates. But those guys didn't necessarily win me over on the first date either.

The one that I was most fond of did not impress me with his earlier messages.

But he kept trying, and every time he would message me he would mention a new activity, like going to the exploratorium, an art show, a secret dinner, urban exploring or a concert, until finally he figured out what worked with me and what didn't.

Whether you're dating or in sales, you need to test enough things to figure out what strategies work for you overall, as well as which techniques and tactics will work with different people, as not everyone will be the same.

Published on: Mar 9, 2016
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