Top 8 Common Sales and Leadership Mistakes (And How to Avoid Them)

Want to fast-track your sales and leadership success? Avoiding these costly mistakes can save you time, money, and frustration.

It is better to learn from others’ experiences than to make the same mistake yourself. While this is good and helpful advice, when an error directly harms you, it stays with you much longer than if you had watched someone else make the same mistake. The rest of this post describes mistakes, missteps, and failures that I learned the hard way. You may have encountered some of them, too. The first five apply to salespeople; the last three are for sales leaders.

Critical Sales Mistakes to Avoid in Your Career

1. Believing My Clients Know More than Me: I spent my early years being a good sales rep, not realizing that I knew more than my clients. This meant I failed to position myself as a peer or trusted advisor. Eventually, I discovered that, most of the time, I was correcting clients’ false assumptions. If you want to avoid this mistake, you must do the work to know more about your client’s problems and what they need to improve their results.
2. Taking Bad Clients: You might believe a deal is a deal, but this is not true. I have had several difficult clients who caused me to waste time chasing payments or stepping in to prevent them from mistreating my team. In some cases, it got to the point where I had to fire these clients. One client even told me he would fire me if I asked to be paid. I fired him instead. The mistake was working with this company in the first place.
3. Over-Serving My Clients: To be fair, these clients were gargantuan. I would visit them in the morning and circle back in the afternoon. While it worked for my clients because I was always available, it prevented me from acquiring other large companies. Eventually, I realized I was spending too much time without increasing my revenue—or, more importantly, my commissions.
4. Wasting Time on Sales Technology: I had email long before most people, and a CRM very early. I wasted time setting up technology. Before these tools, I won deals with a stack of index cards, a Sharpie, a phone, and an index finger. Now, sales leaders believe technology creates efficiency and improves effectiveness. The truth is you are efficient only when you are doing what you need to do, and effective only when your client is engaged with you in a sales conversation.
5. Responding to Low-Value RFPs: I spent a lot of time filling out RFPs because I believed I had a chance. Recently, a young sales rep told me they had a 75 percent chance of winning a deal based solely on their solution and response—without ever speaking to a buyer or decision-maker. If you want to respond, you should first call the client and share something that gives them pause, causing them to ask you what they might have overlooked. No one wants to fail because they missed something important.

Leadership Mistakes That Sabotage Sales Success

1. Believing Everyone Worked Like Me: I became a sales leader at 26 and thought everyone worked the way I did. As it turned out, few matched my effort, with most doing too little throughout the day and week. If you are a sales leader, you want your team to be motivated to match your effort. You need to impose standards around the work that needs to be done and the results you demand.
2. Making Poor Hiring Decisions: The first person to score 99 percent on our assessment turned out to be the worst sales rep I ever hired. He was a good person, but a terrible salesperson. We eventually found him a more suitable role. I learned that it’s critical to ask difficult questions that reveal who you are really hiring.
3. Failing to Protect Your Sales Team: There are people who believe they can contribute to your team’s work—whether by scheduling meetings, advising on your sales methodology, or involving your team in non-sales projects. These individuals are often not in sales roles because they avoid selling, yet they provide advice without the breadth or depth needed to add value. Protect your team from those who would distract them or work against you and your sales force.

Being aware of these eight mistakes will help you avoid similar pitfalls by applying the strategies outlined in each one. By studying these failures, you can save yourself time and avoid poor results you might otherwise encounter by repeating common mistakes.