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This article was published on April 27, 2016

3 sales tricks I learned from dating

3 sales tricks I learned from dating
Hampus Jakobsson
Story by

Hampus Jakobsson

Hampus is the CEO of Brisk, which provides sales productivity tools to companies like Evernote, Hootsuite and Zendesk. In 2002, he co-founde Hampus is the CEO of Brisk, which provides sales productivity tools to companies like Evernote, Hootsuite and Zendesk. In 2002, he co-founded pioneering mobile UI firm TAT which was acquired by Blackberry for $150m in 2010. Hampus is also an angel investor in over 40 startups.

When I was 12, I briefly acquired a girlfriend called Maria. I’m not sure how it started, but I am sure how it ended: badly.

In high-school I dated Eylem, a Kurdish girl. Everything was great when we were alone, but she was distant in public. It took me many years to understand where both relationships went wrong.

Now I run a company which makes tools for salespeople and I’ve noticed that dating requires many of the same skills that you need in sales or customer success.

Sales and dating both involve interacting with another person with a particular goal in mind. And both can be improved with practice. In the digital age, sales often means selling at a distance and at scale using email, messaging and other remote communication methods, just like online dating.

There are three parts to making a sale or building a new relationship: Courting, Politics, and Curriculum.

Part one: Courting


The first thing we learn when dating is how to behave with someone you want to impress: How to ask for things, how to gauge their interest and maybe eventually how to persuade.

In this regard, sales best-practices are good dating best-practices too.

Shut your mouth
First ask questions, then stop talking. Really listen to them.

This might feel hard as you want to show how smart or worthy you are of the other person’s attention (or money). But you must first seek to understand, then to be understood.

Be empathic
Whether you’re dating, doing customer development, or prototyping with customers, you need to understand that the other person is not necessarily like you.

You first need to discover who they are by watching and listening. Don’t rely on what their friends or parents say about them.

Learn more from Bréne Brown and Rob Fitzpatrick on how to listen with empathy.

Emotion trumps logic
The Heath brothers describe the brain as an emotional elephant, with a logical rider sitting top of it.

Elephant and rider stand at a fork in the road – one path tried and tested, the other murky and unknown.

You are the unknown path. It’s not enough to persuade the driver. The emotional elephant needs to feel safe, attracted and excited about this new path. Otherwise the rider is going to have a hard time steering the elephant along the new path.

So speak your prospect’s language and remove all fear, uncertainty and doubt about your path. What are your weak spots? What do they see when they look at you?

Ask, learn, and address.

Part two: Politics

board room

Politics is what happens behind the scenes, when you are not around.

The object of your interest will check you out online and ask others about you. Never underestimate the importance of politics – especially if your “ask” is a big one, like marriage or a large contract.

Sales people have perfected the skill of pushing people to sign but pushing has become less relevant in our digital world, where people have many more choices and do a lot of online research before buying.

Total honesty
If you want a long term relationship (this applies all SaaS sales and some dating) you can’t lie, cheat, or force your way.

Start by understanding what the other party is looking for. If you’re selling a complex service and the other person wants something that just works, whether that’s a relationship or a piece of software, then it’s better to refer them to someone else.

Make them your ambassador
One of the biggest lessons I learned when I built my first company was to empower other people to become our ambassadors.

We give them all the material they needed to show their bosses how amazing we were as well as slides to do internal presentations. We gave them arguments to win over their internal buyer.

I didn’t send pitch decks to my wife before we married, but I’m sure she pitched me to her parents.

Figure out who the decision maker is
Ask how customers make decisions, who makes them, and what products they have previously bought and rejected.

This applies to exes too.

If possible, ask to talk to the decision maker yourself. That way the pitch doesn’t get distorted and the feedback comes clear.

If your new boyfriend’s mom thinks your Facebook picture gives a bad impression, listen to her, apologize, and change it.

After all, it was just spring break…

Part three: Curriculum


Curriculum is sales-speak for what to do when.

We’ve all wondered after a successful first date when to send the next text message. Should I wait for the other person to send it first? Do I sound too eager? Is not hearing anything for a week a bad sign?

The wonderful thing with online sales is that you can track and automate curriculum, because you should have lots of data. You can also do this with online dating.

So what went wrong with my early relationships?

With my high-school sweetheart Eylem, it was politics. Her father didn’t mind her seeing me, but made two things very clear: She was going to marry a Kurdish man and her cousins might not be too nice to me if they knew.

That explains why she was weird in public.

With Maria, well… I was too young to understand that having a relationship requires maintenance. Unfortunately, I also had a knack for choosing women who believe they are low maintenance, when they are in fact they are anything but.

In short, I did not understand the curriculum.

Use the salesman’s knowledge of of courting, politics and curriculum wisely and you might end up with a new love in time for Valentine’s day. Happy Dating!

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