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They say good judgment is the result of prior lousy judgment. That idea has proven true for me over the course of my life in sales. The following stories of nine mistakes are all true, and the name of the person responsible is known to you and cannot be changed to protect the guilty.

  1. Buying Clients: I was very young with a flush expense account to entertain clients or prospects. I had called on a contact at a large company in Century City to schedule a meeting, but all my attempts ended badly. I decided to ask the contact for lunch, and she agreed. She ordered two appetizers, two meals, and two desserts. The second of each course was her dinner later that night. She said hardly a word at lunch. However, by saying nothing, she said everything. Although you will see it done from time to time, you can’t buy clients.
  2. Not Checking for Competitive Threats: After five or six sales calls with a decision-maker, I gained a verbal commitment and scheduled to pick up a contract the following week. Instead, I received a call that he had chosen my competitor. After I had left the building, a competitor presented and showed hi something I didn’t offer. He liked what he saw and changed his mind. I never asked what other options he was considering or if he had seen anything he wanted that I hadn’t shared with him.
  3. Selling Price from Behind: My price was always higher than my competitor’s prices. My strategy was to build the value up before disclosing my higher price as a way to validate it. I had not yet thought of the difference being a more significant investment in the client’s solution, though that is what it was. At some point, I started explaining to prospective clients in the first meeting that my price was higher than my competitors, and the difference in price was how we invested in improving their results. I built the value through the rest of the process. It’s hard to see a higher price at the end of the sale—even when it serves your client to invest.
  4. Big Logos: My small company and I won a lot of huge, well-known clients. I created a slide with all the big logos and added them to a slide deck I used to explain our offerings. Many people were impressed. Several smaller prospects, however, had a negative response to the logos. One of them said, “I believe we might be too small for your company.” I protested, explaining that we were also a small company. What I did not understand for some time was that some clients were looking at the list and recognizing the risk of other, much larger, much more prestigious company they were sure would get the attention they needed. You have to know your audience, and the proof you need should match the client’s concern, not create a new one.
  5. The Front Door Is Locked: I started by calling on people in Human Resources. Most of them would tell me they already had a partner, and that my services were not needed. Some of them would meet with me to learn enough about my company to be able to tell other people on their team, we were not a good fit—and to protect their incumbent. So instead of walking through the front door, I very literally started walking in the back door of buildings and finding the person who used the service I provided. I found my way to the people who wanted better results and were not married to my competitor. The people guarding the front door found out they were going to be using us only after the decision was made by someone who wasn’t getting what they wanted.
  6. Assuming What’s Important: I had a meeting with a client that took me seven years to obtain. To prepare, I read the last three years of their annual reports, including the Chairman’s letters. Having done my homework, I had a list of their three biggest, most strategic initiatives. When I sat down with my contact, I started to describe how my solution could help with the strategic initiatives. He asked me where I came up with those initiatives, and I told him. He replied, “No one in this building cares about any of that. I need people who can drive forklifts. Can you get me those people.” Never one to avoid a necessary change of plans, I quickly said “yes,” without another word about the Chairman’s letter. I overshot the mark by not knowing my audience.
  7. Big Does Not Mean Dream Client: At the time, my largest client was spending millions of dollars with my firm. They were always late on their bill, and they were not good partners. There were many people on their leadership team who brutal to my people—and tried very hard to be tough on me, but lacking in effectiveness due to my demeanor in conflict. At some point, I had enough of how they treated my people and their lack of payment. The CEO of the company told me if I ever asked again or mentioned how they handled my people, he would fire me (using much more colorful language and what he thought was a threatening tone). I calmly told him I expected him to pay me, and that I was sending them the thirty-days notice canceling our contract. The money spent doesn’t mean your client is a dream client.
  8. New Stakeholder: After serving a client for seven years, they hired a new person into a role with authority over my program. The new stakeholder’s power grew as some of my contacts moved out of the company, always taking my team with them because of the better results we provided them. The new stakeholder wanted to make a name for themselves and decided to attack my company and me over our pricing. I defended the investment they were making and did my best to explain why they had made it in the first place. When this stakeholder had the opportunity, they removed us from the company. We continued to work on the stakeholders who knew us, and because of the decisions the new stakeholder made, within a year she was gone. We were back. Because we held so many relationships and did such good work, we suffered from the false illusion that we were safe. We were not.
  9. Not Leading: As a young leader, I found it challenging to get the results I need through others. I started with a terrible premise. I assumed that all people were just like me, self-starters, needing no direction or leadership. That plan, as you might have guessed, was a disaster. I doubled down on that bet by hiring experienced people and compensating them so I wouldn’t have to lead them. The results were even worse. After spending too much time and way too much money, I accepted that everything was my fault, and I started to lead.

There is no substitute for experience when it comes to your growth and development. You can learn as much from your mistakes as you can your successes if you derive the lessons and avoid them in the future. What mistakes have you made, and what did you learn from them?

Sales 2019
Post by Anthony Iannarino on August 14, 2019

Written and edited by human brains and human hands.

Anthony Iannarino
Anthony Iannarino is a writer, an international speaker, and an entrepreneur. He is the author of four books on the modern sales approach, one book on sales leadership, and his latest book called The Negativity Fast releases on 10.31.23. Anthony posts daily content here at TheSalesBlog.com.
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