I Worked in Sales for 13 Years — Here’s What I Learned

Moving product has very little to do with actively pitching

Tim Denning
Jul 24 · 6 min read
Photo by LinkedIn Sales Navigator on Unsplash

Working in sales was something I never set out to do. It happened by accident when I was in a family business and the only job left was sales. When I began selling, I sucked. Leads would literally hang up on me the moment I dialed their number and attempted to introduce myself.

Fast forward 13 years, and I have learned many lessons about selling. The biggest lesson of all is this: we’re selling in our day-to-day lives every day whether we realize it or not.

That’s why I wrote this article. If ever there was going to be a life skill that could help you, it’s selling.

Take it from someone who was a skeptic and used to think that good products sell themselves — they don’t. Humans sell products to humans through the art of selling.

1. Passion for the Customer

Customers can sense when you care and when you are trying to make a commission off them. Having a passion for the customer is about deeply caring for their problem.

The excitement of solving the problem and seeing the customer win is what drives high-performing salespeople.

The best example I have seen in the last 13 years is when one of my colleagues was sitting at a showcase presentation to display the latest innovative ideas. Her one and only enterprise client got named in the presentation. My colleague stood up and cheered for her client in front of a group of conservative (mostly) strangers and risked looking like a total idiot. Cheering her customer on and showing them how much she cared was worth a minute or two of awkwardness.

When you are really passionate about your client, you do crazy sh*t like this because you are truly passionate and not just pretending to be.

Once a client sees this sort of passion in you and feels that it’s real, they will walk over hot coals to do business with you, and they’ll fend off your competitors. That is the power of passion.

2. Have Empathy for the Customer’s Problem

A problem can only be understood fully when you feel what your clients feel and can talk to them on that level.

Empathy wins customers in secret every day. In my own career, when one of my clients is feeling pain, I feel their pain too.

One such example that stands out after so many years is when a company I was working for had major technology outages. They lasted for weeks and weeks. Our clients were agitated, and we were trying everything to resolve the problem.

I had many sleepless nights during those few weeks. I pictured the clients dealing with their direct customers’ frustration and not being able to enjoy the simple pleasures in life, such as holidays and takeaway food on footy night.

The pain that I was feeling was what drove me to do abnormal tasks to try and resolve the problem. I didn’t want to feel the pain any longer and neither did my client. What hurts them also hurts me.

Developing empathy for a client is how you talk to them on a different level, one that is much deeper and longer-lasting than a transactional relationship will ever be.

3. Practice Humility, Not Selling

The biggest blocker to selling a product or a service is you.

And by you, I mean you and your ego. Being humble when you sell is infectious to customers because it’s so rare.

In 2014, I went after a client ferociously and lost. Everything that could be done was done. The relationship was strong and the trust was definitely there. But after all of that, they chose another supplier and I was gutted.

In defeat, I was humble and wished the client all the best. Staying in touch was important to me because I wanted to ensure they ended up where they aimed to be.

Three years on, the client didn’t get the results they were sold. Because I had kept in touch, they asked me to help. I offered the help for free. At no stage did I pretend I was better or insinuate that the client had made a bad decision — that is what your ego tells a client.

By seeing the problem for what it was and not trying to directly sell my solution in an over-the-top way, the client went from frustration to appreciation.

This is how you can act humble when you are selling. Ultimately, you win more deals by being humble even if you don’t succeed the first time.

4. Truly Understand the Problem

Solutions that are sold on a daily basis don’t solve the customer’s core problem. They pretend to solve a problem. Understanding a client’s problem takes patience, time, and your full attention. The problem always looks simple at the beginning until you dig deeper.

The way to solve a client’s problem is to become a well-crafted artist in asking questions. Questions such as:

The questions go on and on. What starts out as the original problem often is a symptom of the actual problem.

You have to dig deep to the heart of what is going on, and when you do, you’ll understand a customer’s problem on an entirely different level. That will give you a competitive advantage.

5. Listen More Than You Talk

Customers want to be heard above all else. A simple test you can do is to estimate after a sales meeting how much time you were talking and how much the client was talking.

I always try to allow the client to do at least 60% of the talking. Inserting gaps of silence to let the client take in what I’ve said is important as well.

Silence allows a customer to think. Filling up an entire meeting with your own voice demonstrates that you don’t care and you’re not willing to see the client’s problem in all its glory so that you can eventually solve it.

6. Build Relationships Rather Than Acquire Customers

Relationships is the most overused word in sales. It’s often a misused term.

Here’s the difference:

A relationship is built on trust. This means taking actions that may not be in your best interests or the interests of reaching your sales target, but rather always doing the right thing for your client.

The silly thing is that when you take actions that may stop you from selling or hitting your sales target, you get a whole lot of hidden benefits such as:

Aim for relationships with people, and you will become uncommon and produce sales results in the long-term that look unattainable from the outside.

7. Be OK With Losing

Selling is tough because you have to accept that you will probably lose more times than you win.

You have to learn to lose and be able to see the lessons and areas for improvement so that you can win next time. If you don’t handle losing or rejection well, it can be tough to sell.

Disconnecting from the outcome is how you overcome the feelings associated with losing and continue moving forward.


Each of these lessons can be applied in life — they’re not just designed for selling a product or service in a business context.

You are selling when you:

Everything you do will involve you influencing another human being, and that is selling. Selling doesn’t have to be scary if you take the human approach.

The human approach is always to treat someone with care, respect, and honesty. If you do this, you can sell literally anything to anyone.

Better Marketing

Advice & case studies

Tim Denning

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Viral Blogger - Inspiring the world through Personal Development and Entrepreneurship. www.timdenning.net

Better Marketing

Advice & case studies

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