The Worst Sales Mistakes I Have Ever Made

As I emerged from a great vacation with my family, I had a lot of time to reflect on my career. After 12 years in sales, I couldn’t help but think about some of the worst sales mistakes I’ve made – because these are what teach me the most.

As with most lessons learned, I’ve gained insight through trial and error by making some significant sales mistakes.

Learning from your mistakes can be a challenge. It often takes honest introspection and determination to change. However, the benefits outweigh the effort – each and every time.

Here are five of the worst sales mistakes I have ever made. I’ve done the heavy lifting, so maybe you won’t have to.


1. Taking Rejection Personally

After graduating from Miami University (Ohio) with a degree in exercise science, I started my first job out of school cold calling businesses and selling computers. Considering I had no background in business or sales, it took me a while to learn not to take rejection personally. After receiving significant sales training, I hit the phones.

Needless to say, handling rejection came early and often. Unfortunately, I took things too personally, which made me question if I was cut out for sales. Luckily I decided to have fun, laugh and learn from my failures. This decision helped me maintain a positive attitude and continue developing a great sales career.

Sales Tip: Learn from every experience and stay positive. Don’t take rejection personally.

2. Acting like I Knew More Than I Really Did

With the daily expectation to make 100 calls to CTOs and CIOs of large companies, I quickly found myself in very high-level technical conversations that I had no business being a part of.

Being young and dumb, I subscribed to the mantra: “Fake it ‘til you make it.” However, prospective clients saw through my guise and discredited me as a reliable source. I lost many opportunities to secure great clients due to this mentality.

Sales Tip: Be honest and genuine. Prospects will respect you more if you point them to the resource they really need.

3. Thinking That I Knew Enough

Unfortunately for many sales professionals (including, for a while, myself), learning typically stops after college. As I became comfortable in my sales position, my hunger for continual knowledge subsided.

Once we started Acquirent, I realized that there was so much more that I needed to learn. In order to keep up with new advancements, I need to read, listen and learn constantly. Today I make it a point to read and absorb as much as I can to stay ahead of the pack.

Sales Tip: Challenge yourself to learn at every occasion, and keep learning no matter how far you are in your career.

4. Valuing My Commission, Not the Customer

A number of times I concentrated too heavily on what my commission check would look like from a sale instead of how I could help a customer. Every single time I did this, I lost the customer, and the commission check.

In the end, I realized that by concentrating on caring for my customer first, my commission check would be taken care of as well.

Sales Tip: Provide value to the customer and everyone wins.

5. Not Asking for the Close

On occasion, after paying attention to my customer’s needs, building rapport, answering questions and serving as a resource, I would scratch my head when my manager would ask “Why hasn’t this closed?”

Pouring through my notes and reviewing old emails didn’t reveal an answer. Until a lightbulb went off: I never asked for the close. It took several losses to realize the customer often waits on you to initiate the closing process.

Sales Tip: Ask for the close and start closing more sales.

Don’t make my worst sales mistakes – learn from them. As you make your own blunders, find the lesson and move forward all the wiser.

Happy selling!