4 Sales Mistakes Costing You Clients—and How to Fix Them

Nearly two decades ago I started my career in the automotive industry. Like many of us, I got into the business by accident. I needed a job fast, the barriers to entry were fairly low, and I wondered how hard it could actually be. I’m grateful that I had an incredible mentor in Jack Clagg who taught me a simple and human-centered approach to sales. I’m profoundly grateful for his wisdom, mentorship, and the foundational knowledge he shared for me to be able to have a successful career. Since then, I’ve been training salespeople—first in the car business and now in a host of different industries. 

Over the past 17 years, I’ve observed four key mistakes that prevent individuals from achieving more sales success. 

Mistake #1: Salespeople have the wrong mindset. 

This single point could be a book, but let me tease out some of the ways that I have seen this show up. 

First, salespeople typically don’t have generous intent for their prospects and clients. They take the approach that a client is an adversary or an opponent to be engaged with rather than a person that can be served. Cynicism sneaks in and we start making assumptions about our prospective client and their situation. We then build our sales approach on this false foundation. As a result, competitiveness and jockeying for power in the negotiation starts to up the tension. Don’t misunderstand me, I’m one of the more competitive people you will meet, but I also have had to learn that I get more of what I want when I help others get what they want, to paraphrase Zig Ziglar. 

Secondly, a significant number of salespeople lack confidence in their product and themselves. Their lack of belief directly correlates to a lack of sales. This isn’t about faking it till you make it. It’s about an intimate understanding of your product, your own strengths as a salesperson, and the unique problem your product solves. It’s about practicing the craft and believing you actually have something valuable to offer that will improve someone’s life or business. And it’s about having the confidence to be the process leader. Salespeople try to be deferential to customers and allow them to lead the process because they don’t want to lose the sale. A prospect will be more decisive and pay more for strong sales process leadership. 

Lastly, salespeople take rejection personally as opposed to an opportunity to learn. Every “no” affords us with a chance to improve our skills. These get missed when we hear someone saying “no” to us, as opposed to our product. This results in a spiral in which salespeople start creating objections and answering them before a prospective client even raises them. We refer to this as negative thinking, which I think is a bit of a misnomer. I would call it confirmation bias. C.S. Lewis famously wrote, “Suspicion often creates what it suspects.” If we are looking for objections, we will find plenty. If we are looking for opportunities, we will find more than we could ever imagine. 

Mistake #2: Salespeople are too focused on outcomes. I once had a client who had a death grip on outcomes. If he met someone, he would wonder when they were going to become a client, which created a vicious, anxious spiral. He failed to focus on the process because of his obsession with the results. The best athletes are the ones who are in love with the process. Consider Tom Brady or current PGA superstar Scottie Scheffler. When they are interviewed, they share how much they love practicing and executing each individual play or shot with excellence. The same goes for the highest performing salespeople. They are focused on winning each step of the process rather than winning the game. It’s the sum of all the parts that makes up the whole. When we understand that outcomes are merely a collection of steps executed with excellence, the sales take care of themselves. 

Mistake #3: Salespeople solve the wrong problem for the wrong people. I’ve observed salespeople trying to motivate customers to value what is most important to them rather than what is most important to the customer. On the one hand this is because the salesperson may be providing a great solution to someone who is not their ideal client. On the other hand, it could very well be that the solution that they are providing doesn’t solve the prospective client’s actual problem. A misunderstanding of the problem and the prospect often results in what people refer to as “pushiness” or what I would say is borderline manipulation. When we provide a real solution to our client’s problems, the sale is obvious and natural. 

I recall showing up to a meeting with an individual who is now my client. We had been talking for a few months and had agreed to get together for lunch. She had a rapidly growing business that she wanted to bring a proven strategic operating system so she could harness her team’s power. It was the exact solution she was looking for. She asked me what my fee was. I told her. She said send me the agreement. She signed it, and we have been working together for a few months now. Oh, that sounds so easy, Josh. Well, it was. Why? Because I took the time to understand her real problem and I brought a solution that solved it. It was a no-brainer to sign up. 

Mistake #4: Salespeople lack good communication skills. In that story I just shared, I learned about what this client was looking for by asking questions with the intent to gain understanding. I wasn’t looking for opportunities to prop myself up, demonstrate the value of my product, or anything else. I can’t help anyone if I don’t understand what the real issue is. Here’s a hint: the real issue isn’t usually what someone explains at the outset. Take, for instance, a meeting I recently had with another prospective client. They shared with me some struggles they were having with their agreements. I asked them lots of questions and what I (and they) learned was that they were trying to create this whole new agreement because they had a lot of clients who weren’t ideal and didn’t share their values. So what showed up as needing help with an agreement actually was a marketing and client enrollment problem. The only way to uncover that was to be curious. I was in no hurry to solve that problem until I properly understood it. 

One of the most valuable skills that I have learned in sales is to slow down to get better results. I’m not talking about delaying, but I’m also not talking about rushing. Consider what happens when we provide the wrong solutions to a problem. We’ve lost our prospective client’s trust and we have to start over. Clients always want to know the price but if we offer that before we understand their problem, that results in a critical error that’s really difficult to recover from. Frankly, I’ve always thought that putting a premium on someone’s ability to talk fast and rush the process was a mistake. Yet, as a society, we have glorified that, and it’s the single most significant error that salespeople make. They talk too much. If they would be patient and curious enough, their prospective client would offer them all the information they need to make the sales process the easiest one they’ve ever been through. 

I never intended to include sales training in my coaching practice. However, after many individuals came to ask me if I would help them with their business development efforts, I became curious about how I could serve them. As a few of them became clients, I observed similar patterns in the discussions I was having. Then I began to see the positive impact of our work together. They were multiplying the fee they were paying me and they were increasing their incomes by 10-30%. I started to wonder what could make it even stronger. I concluded that a group of people doing this together could be even more impactful than the one-to-one coaching I was doing. And so the Bethesda Sales Academy was born. The inaugural cohort for this program starts in mid-September. If you are interested in learning more, reply to this email and I’m happy to share the details and see if it could be a good fit.