Going on 3 Dates a Week Dramatically Improved My Sales Skills. Here Are the Biggest Lessons I Learned.

I went on three dates a week for a year. As a byproduct, I accidentally improved my sales skills. Here's what I learned.

learn more about Dejon Brooks

By Dejon Brooks

Opinions expressed by Entrepreneur contributors are their own.

As I entered my 20s at the beginning of 2021, I decided to move out of my parents' house. I wanted to start fresh socially and move somewhere far away from home. Fast-forward six months, and I've successfully moved from Atlanta, Georgia to Provo, Utah. When I arrived in Provo, I had no friends. Even though there are two significant universities down the street, I realized that I had to put myself out there and meet new people.

To do this, I set a goal to meet two new people a day. Not only did this allow me to make new friends, but I naturally crossed paths with people I was compatible with. Some of these people, I asked out on dates.

Keep in mind, while I was growing up, I never went on any dates — so I had no dating experience. But after meeting two new people a day, not only did I start going on dates, but as a byproduct, 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. Everything comes down to timing

One of the first lessons I learned from going on three dates a week is that everything comes down to timing. Not just timing as in being ready for a relationship or marriage but also when it comes juggling the timing between school, work, family, travel and so many other factors.

This is why I am 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 blasts are so powerful.

Someone who is not interested today could be ready to buy six months down the road. You just have to be consistent and catch them at the right time. Because of this insight, I've spent a lot of time learning how I can maximize email marketing within my business. Once I have email marketing mastered, I'll next start looking into other advanced retargeting methods.

2. Not everyone is interested

Within the last year, I've been able to individually meet over 3,000 people (both guys and girls) because of my goal of meeting two new people each day. This includes learning their name and speaking with them for at least 2-3 minutes.

After interacting with this many people around my age range, I quickly learned that not everyone is going to like me. When it comes to finding people you are compatible with, you have to play the numbers game until you find someone who likes you.

I noticed that everything becomes easier when you find people who truly like you for who you are. This is not only true with dating but for just about everything else, including sales. All of my best customers came from people who were truly interested in what I had to offer. Some of them did require a push on the back to help them make the leap, but they were interested.

Related: 6 Tried and Tested Methods to Improve Your Sales Skills

3. How to ask great questions

One thing dating has taught me is how to ask great questions. Icebreaker questions are nice, but after going on 100+ dates within the past year, you start wanting deeper and more meaningful interactions.

You want to understand people's pasts and how it shaped them into the person they are today. You want to understand their thought process, how they handle conflict, etc. You slowly start appreciating the internal more than the external.

To uncover the internal attributes, you must learn to ask great questions and become a good listener. All of my first dates are meaningful coffee shop dates where we get to learn about each other's life stories. Some of the questions I love asking are:

  • Why did your last relationship end, what did you learn from it? How has it shaped you into the person you are today?

  • What are red/green flags you look for when dating?

  • What is your relationship like with your family?

  • What is your defining moment?

  • What are your dealbreakers?

  • How do you handle conflict?

Learning to take time to understand someone and ask the right kinds of questions truly has helped me improve my sales skills exponentially. It allowed me to understand the customer's pain point and provide them with the best solution that will fix their problem.

Related: The 3 Most Important Skills in Sales

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

I don't recommend going on three dates a week, though. It is exhausting emotionally and financially, but thankfully, I was able to learn a lot from it. What you should do is make an attempt to meet new people as often as you can. Doing so 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.

Dejon Brooks

Entrepreneur Leadership Network Contributor

CEO & Founder of Trend Watchers

Dejon Brooks is an entrepreneur who founded Trend Watchers with his life savings. Aged 21, Dejon has turned Trend Watchers into a successful business. After reaching over 100M+ people on his personal accounts, he now helps content creators go viral by taking advantage of internet trends.

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