How Going to 3 Dates a Week Improved My Sales Skills

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As I entered my twenties in early 2021, I decided to move out of my parents’ house. I wanted to make a new social start and move away from home. Fast forward six months, and I successfully moved from Atlanta, Georgia to Provo, Utah. When I came to Provo, I had no friends. Even though there are two major universities down the street, I realized that I had to stand out and meet new people.

To do this, I set myself the goal of meeting two new people a day. Not only did it allow me to make new friends, but I naturally met people with whom I was compatible. Some of these people I asked for dates.

Keep in mind that while I was growing up, I never dated – so I had no dating experience. But after meeting two new people a day, not only did I start dating, but as a by-product, I ended up improving my sales skills by accident. Here are three important things I learned from my experience:

Related: Take your sales skills to the next level with these 5 simple steps

1. Timing is everything

One of the first lessons I learned from going on three dates a week is that it’s all about timing. Not just timing like getting ready for a relationship or marriage, but also when it comes to juggling timing between school, work, family, travel and so many other factors.

That’s why I’m obsessed with email marketing. Email marketing sounds lame and old, but it takes advantage of one key thing: catching people at the right time. This is why weekly email sends are so powerful.

Someone who isn’t interested today might be ready to buy in six months. Just be consistent and catch them at the right time. Thanks to this idea, I spent a lot of time learning how to maximize email marketing within my business. Once I’ve mastered email marketing, I’ll start investigating other advanced retargeting methods.

2. Not everyone is interested

Over the past year, I have been able to meet over 3,000 people individually (boys and girls) due to my goal of meeting two new people every day. This includes learning their name and speaking with them for at least 2-3 minutes.

After interacting with so many people in my age bracket, I quickly realized that not everyone would like me. When it comes to finding people you’re compatible with, you have to play the numbers game until you find someone who likes you.

I’ve noticed that everything becomes easier when you find people who really love you for who you are. This isn’t just true for dating, but for just about everything else, including sales. All of my best clients came from people who were genuinely interested in what I had to offer. Some of them needed a push on the back to help them take the leap, but they were interested.

Related: 6 Tried and Tested Ways to Improve Your Selling Skills

3. How to ask good questions

One thing dating has taught me is how to ask good questions. Icebreaker questions are nice, but after going on 100+ dates over the past year, you’re starting to crave deeper, more meaningful interactions.

You want to understand people’s past and how it shaped them to become the person they are today. You want to understand their thought process, how they handle conflict, etc. You slowly begin to appreciate the inside more than the outside.

To discover internal attributes, you must learn to ask big questions and become a good listener. All of my first dates are meaningful dates at a coffee shop where we get to know each other’s life story. Some of the questions I like to ask are:

  • Why did your last relationship end, what did you learn from it? How did that make you the person you are today?

  • What are the red/green flags you look for when going out?

  • What is your relationship with your family?

  • What is your defining moment?

  • Who are your dealbreakers?

  • How do you handle conflict?

Learning to take the time to understand someone and ask the right questions has really helped me improve my selling skills exponentially. This allowed me to understand the customer’s pain point and provide them with the best solution that will solve their problem.

Related: The 3 Most Important Sales Skills

As someone who had never dated before, going on three dates a week for the past year has taught me a lot. Not only did I learn a lot of relationship building skills, but I was also able to significantly improve my social and sales skills as a bonus.

I don’t recommend going on three dates a week, though. It’s emotionally and financially draining, but luckily I was able to learn a lot. What you should do is try to meet new people as often as possible. It will teach you the importance of timing, help you understand and accept that not everyone is interested, and allow you to ask better questions as your sales skills improve.