The Advisory Career

Five Common Sales Obstacles and How to Overcome Them

A Salesperson’s Handbook

by Paul Cherry

Mr. Cherry is President of Performance Based Results and is the leading authority on customer engagement strategies. He has more than 23 years’ experience in sales training, leadership development, sales performance coaching and management coaching. He is also the author of Questions that Sell: The Powerful Process for Discovering What Your Customer Really Wants and Questions that Get Results: Innovative Ideas Managers Can Use to Improve Their Team’s Performance. For more information on Paul, please visit You can also reach him at 302-478-4443 or

Lucy was a brand new salesperson who wanted to make a big impression. She did everything she could think of to establish relationships with prospects and wow them with her proposals. While she was not failing as a salesperson, Lucy was certainly not leading her team in sales either.

After nine months of below average performances, she knew something had to change—but what? Veteran salespeople know that while every customer is unique, the obstacles to a sale are predictably the same and occur rather frequently. Once you understand these obstacles and the strategies to overcome them, you will have all of the tools you need to make the sale.

Obstacle 1: Identifying and Communicating with the Decision Maker(s)

Too often, salespeople will focus solely on their initial contact at an organization. Whether that person is a mid-level manager or an HR executive, they are probably not the only person who is going to have input on the proposal process. Smart salespeople know that there are usually other decision makers who will have input in the deal, and the challenge is to figure out who they are and how you can meet with them. In order to get the information you want, you will to have to ask your current contact some questions that might seem awkward. Some questions to broach the issue are:

  • What is your time frame for making a final decision?
  • What criteria will you be evaluating to ensure you are making the best decision?
  • What measurable outcomes are you looking to achieve?
  • Once you are able to determine who else will be involved in the decision making process, you can ask this follow up question: “I really appreciate this insight. So that I can propose the best solution that is going to meet the needs of everyone else involved, I would love to talk with these other individuals and get their input. When can I meet with them?”

Obstacle 2: Uncovering the Budget

Nothing will derail a deal faster than a mismatch between your proposal and the customer’s budget. Unfortunately, prospects are often reluctant to discuss their budgets with salespeople. It is your job to press them further to get a number, or at the very least, a range of what their budget is for the project.

There are two options to making this happen. You can politely—but firmly—suggest that your prospect determine their budget prior to soliciting bids. Stress the importance of an advance figure, and express your interest in receiving them before you reconnect. This approach puts the focus on the prospect, not you. It tells them that you care about them and their financial security and you do not want them to make a mistake.

If you sell on price, you lose on price

The second option involves framing the interaction through the lens of recommending a program that best suits your prospect’s needs and expectations, and expressing how budget parameters can shape the direction for both parties. If they say they cannot give you a number because they’re not the ones putting the budget together, ask to be introduced to those who are involved in crafting the budget. This will minimize price objections later on in the process, especially when you are put in front of people who are not as concerned with budget, as they are with their ROI.

Obstacle 3: Working with Customers

Who Do Not Want to Commit There is nothing more frustrating that getting ready to close a sale, only to have a customer say, “I still need to think about it.” When this happens, a seasoned salesperson knows that he or she needs to follow up on the customer’s statement. You should respond by saying: “I can understand you need to think about this.

After all, it is an important decision and you need to do what is best for you and your organization. Tell me, what specifically stands out from our conversation that is of interest to you?” The goal of this question is to get clarification on how much the prospect is really interested in what you have shared and whether or not the prospect feels they want to move forward. Is there sincerity in the response, or are you being blown off? Once you get an answer to your first question, you can acknowledge that the customer has concerns, and ask them what they are.

Ask what is holding them back from making a decision, and then hopefully you can help alleviate their concerns and get the sale back on track.

Obstacle 4: Understanding the Customer’s Values

Too often, salespeople get stuck on the issue of price. If you sell on price, you lose on price.

As soon as someone cheaper comes along, a customer will not give you a second thought before cutting you loose. Instead of getting caught up in price wars, you need to steer a customer’s attention to other issues. This means you need to ask your customers about value. What characteristics does the organization value in a vendor? Are they most concerned with good customer service, high quality products, speedy delivery, or ease of use?

Once you get a customer talking about these areas, you can determine what their needs are and how you can position yourself to get those needs met.

Obstacle 5: Establishing Your Credibility

Many salespeople make the mistake of spending an initial meeting talking all about themselves and their products. This is a mistake. During an initial call, your goal should be for the prospect to do 70% of the talking. Why? For two reasons:

  • 1. You want to hear about his/her problems, goals, concerns and ideas
  • 2. You want to qualify if there is a genuine opportunity with this prospect

You cannot do either of those things if you are trying to sell during the first meeting. As much as you want to sell yourself, you should never bring out PowerPoint, samples or company literature during an initial meeting. What should you do at an initial meeting? You should start the meeting with a unique value opening statement, which is a 30-60 second description of who you are as a company and what you do. The value opening statement should detail the benefits of your company to the prospect, the impact that hiring you will have to their organization, and an immediate follow-up question to gauge their expectations and interest.

Remember Lucy? She started to utilize these tips and strategies with her customers. She found that she was able to ask great questions of her customers and this in turn led to increased sales and increased overall performance in her office.