When Good People Are Bad Salespeople

No good person wants to believe that they are a terrible salesman. Sure, you have to be a bad salesperson before you can become a good one, but you’re incredibly unlikely to be the Hitler of B2B sales if you have at least an average moral intelligence (MQ). In my book, a good measure of a salesperson’s MQ is whether they think selling is something you do to someone or for someone. But here’s a confession: the story of how I became a really bad salesman and (eventually) a better one.

The Center Cannot Hold

I was among the best sales people, you see, before my manager forced me into outside sales. When I worked in operations, I called prospective clients and asked them for meetings. A good number of them agreed to meet with me, and because I had a few years of experience solving my client’s problems, I was able to recognize their challenges and suggest to them some ways I might be able to help. Winning deals was nothing more than asking for a chance to help.

I had no quota and I wasn’t responsible for scheduling new meetings, even though I was able to meet new prospective clients every week. But once I was given the title of Field Salesperson in Los Angeles, things immediately fell apart. I became a bad salesperson.

Mistake 1: A Change in My Intentions

My first mistake came right away. Instead of calling people to see if I could meet with them to help them solve the problems I knew how to solve, I started calling them to “secure a meeting.” Before being thrown into a sales role, I had no trouble getting meetings. I went from not worrying about whether I got a meeting to “needing” to get a meeting. I was no longer focused on helping the prospect succeed, but on what I needed to succeed in my role. This change in mindset made me a terrible salesman, despite once being one of the best sales people.

It’s important to note here that my manager didn’t put any pressure on me to schedule meetings. The fact that I had some weeks with a single meeting and some weeks with three meetings was never mentioned. But I had read a then-popular book on sales (no, I won’t tell you which one), which offered me a hard approach to sales that I was far too immature to use effectively. I came to believe that everything came down to how many meetings I could schedule. Luckily, that book’s model soon made me feel bad about myself, so I abandoned it, but the damage was done.

Mistake 2: Trying Way Too Hard

My second mistake was changing my discovery process. When I wasn’t a salesperson, I asked a few very natural questions about the client’s usage of the service I sold, and I gave them a tremendous amount of space to share with me. I was a very good listener and a good student, paying attention to the clients.

But once I gained some “real” sales experience, I started to dominate the discovery process, spending more time talking and less time listening. I was armed with solutions, and the minute my unfortunate prospects shared their issues I started to solve them one by one, without so much as a follow-up question. I was trying way too hard to solve their problems, and in doing so, I alienated many of my prospects. It suddenly became much more difficult to get a contract and to earn their business.

Mistake 3: Pitching Like the Devil

Once I was trained to sell, I caused a staggering amount of harm to my prospective deals. If bad selling were a crime, I’d be praying that the statute of limitations has run out by now.

As a new salesperson, I was provided with an 84-page monster of a proposal to present to my clients. It started with the company’s history, followed by our approach, and finally listed every feature, benefit, and advantage known to the industry. When I say that I literally read the proposal to them from front to back, I mean that I did exactly that, with no deviations. There are people who still haven’t recovered from the yawnfest that was my presentation—it could spawn a sleep so deep that it would make a fairy-tale villain jealous.

At the time, it never dawned on me that back before I was a salesperson, I had never walked into any meeting with anything more than a legal pad, a pen, and business card. I never had a brochure, a presentation, or any sales collateral. Yet, I went from effortlessly winning deals to struggling and losing what were not even opportunities.

Back to the Garden

It took me far too many months to give up that approach. I didn’t give up on selling, though. In fact, in spite of all the obstacles I was putting in my own way, I knew I was never, ever going back to working in operations. The reason was simple: I realized that I could do more to help my clients in sales than I ever could in an operational role. Why solve small problems when you can help solve larger ones?

Armed with that insight, I went back to what I was doing when I wasn’t a salesperson. My results immediately started to improve. I got less frustrated and worried less about any one particular outcome, instead “trusting the process” of making cold calls, believing the prospect would tell me what I needed to know, and asking if I could have a chance to help them. The outcomes eventually took care of themselves, something that only happens if you consistently do the work.

The reason good people are sometimes bad salespeople is that selling is difficult. It takes time, training, and development that only comes from experience, so we can improve the complex, dynamic, nonlinear conversations that we engage in when we sell.