How I failed in my first sales job

Back in the late 1990’s, I was studying a business degree full-time at university. But I was getting bored with my part-time job at the hardware store. I wanted to feel the excitement of being part of a business and not just reading about it in a textbook.

Something needed to change!

After speaking with my friend, Chris he offered me my first sales job selling door-to-door security products. The work was commission-only, meaning if I would only be paid when a sale was made.

Chris took me out on a trial run and the work felt exciting and potentially profitable. Chris was a sales pro. He had developed a very relaxed approach to greet people at the door and make them feel comfortable. He connected instantly with people by being curious and light-hearted at the same time.

When he identified a suitable customer, he adjusted from relaxed to a razor-sharp sales pitch which gave him a very high success rate. However when he could not qualify them as a good customer, he would stay in his relaxed position and relocate to the next house.

Chris possessed a vast library of sales and influencing skills that simply went over my head at the time.

Feeling high in self-confidence I decided to give it a go. The first few weeks I was earning slightly higher than my previous job. I would usually only need to knock on doors for a 90-minute session a few times a week to earn a comfortable student living.

Then I had this brilliant idea. I decided to sell for an entire Saturday and make my biggest sale ever! My goal was to make enough money to afford a short holiday.

So the next Saturday I started nice and early. My energy and motivation was high because I knew what I wanted – more money!

The first hour of selling went by. No sales. That was okay. But then it stretched to two hours. I was feeling a bit anxious. I had ever gone this long without a sale. Was I doing something wrong? Was I targeting the wrong people?

Without realising it I had stopped trying to connect with my potential customers, and just my internal questions and fears. I finally made it to four hours of selling. I had come close but no sales. After lunch I kept going. This time I was on autopilot. I needed to talk to as many people as possible!

Finally after six hours of no sales results, I gave up.


Feelings of both failure and frustration swept my mind.

I concluded I did not have the charismatic or outgoing nature to ever be successful in selling.

Fast forward 20+ years, I have been fortunate to have had a rewarding career in sales. I would not swap it for any other job in the world.

David Mayer and Herbert M. Greenberg wrote a wonderful article in the Harvard Business Review (HBR) entitled, What Makes a Good Salesman (2006).

To put it simply the best sales people have the following two characteristics:

  1. They have strong customer empathy skills
  2. They also have strong “ego drive” to achieve success

When these two characteristics are both high and with a salesperson, their chances of success will skyrocket.

In hindsight my friend, Chris had developed these skills in his door-to-door business. He developed a great connection with potential customers, knowing how to relate to them instantly. He also possessed high ego drive. Behind that relaxed exterior was a focussed and calculating sales professional who was highly motivated to achieve his numbers.

Key takeaways

  1. As a startup founder, reflect on how you are connecting with your potential customers. Do you know how they are feeling? Do they feel you understand them? If the answer is maybe, then perhaps you can work on that?
  2. Secondly we all need to feel accountable. It can provide positive pressure for us to reach the “unachievable”. I invite you to find a coach or mentor that will keep you focused constantly on achieving both short-term and long term sales goals.

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