The 12 Deadly Sins of Sales Questioning – Are you Guilty?

Are you a good questioner? Most sales reps are not. Here is a list of the twelve most common “sins” made by tele-sales reps (or field reps for that matter) and what you can do about them. Are you guilty of any of these mistakes?

Deadly Sin #1:  Not Asking Questions at All

Still, after the millions of words that have been written about the importance and value of questioning, there are sales reps that continue to ignore the advice and simply pitch the product. Asking questions gets clients involved by getting THEM to tell YOU what they want or need or think is important. When they’re involved, they are more likely to buy. To solve this blunder, stop talking and start asking.

Deadly Sin #2:  Asking Dumb and Destructive Questions

Don’t be fooled, there ARE dumb questions. For instance, “What do you like about your current supplier?” is a particularly dumb and destructive question. This question gets the client to open up and verbally ‘testify’ why they like your competitor. In effect, it justifies and reinforces their rationale for choosing their vendor which makes your job even tougher. What to do? THINK about the questions you are going to ask before you ask them.

Deadly Sin #3:  Asking too Many Questions

While questions are good and necessary in the selling process too much of a good thing can be dangerous. Asking too many questions can overwhelm, bore or frustrate your client and YOU. Ask yourself: What do I really need to know from the customer or prospect?” Focus on these questions to ensure you get what you need.

Deadly Sin # 4: Asking too Many Open Ended Questions

Open ended questions are often positioned as the Holy Grail of questions because they get the client to ‘open up’ and provide vital information on their problems, predicaments, pains, opportunities, challenges and the like. However, the truth of the matter is too many open ended questions can be destructive. Unless they are relevant and pertinent, they can confuse, bore, annoy, overwhelm, and bewilder the client. They can often lead you down paths you don’t want to go. The solution is twofold: carefully select your open ended questions and then direct and point the discussion with the judicious use of closed ended questions.

Deadly Sin # 5:  Asking too Many Close Ended Questions

Closed ended questions are short answer or yes or no type answers. When used wisely they are handy little helpers that verify, clarify and confirm information. In addition they can help direct the questioning so you can identify needs more quickly and easily. The problem occurs when they are overused which tends to make buyers feel they are being grilled or interrogated. Surveys reveal that after three or four consecutive close ended questions buyers feel frustration; beyond that they are annoyed or hostile and will disengage from the conversation. Regrettably, the majority of reps tend to use more closed ended questions than open ended.

The Incredible Questioning Guide

The trick to balancing close and open ended questions is to create a Questioning Guide Chart. Take a sheet of paper and draw a line down the middle. On the left side, list all the INFORMATION you need to help understand the client’s situation, needs, wants etc. On the right side, list the QUESTIONS that you need to ask in order to get the information. What you will find is that most of your questions end up being close ended. Revamp those questions so there is mix of open and closed. You can use this chart to help you deal with virtually all of the blunders listed here.

Deadly Sin #6: Not Asking Bold Questions

Bold questions are qualifying questions that many reps seem to avoid or forget. They are called bold because sometimes it takes a little nerve to ask them but in doing so you can save time by cutting to the quick and determining if the prospect has potential or not.

One bold question is the decision maker question: “Apart from yourself, Jim, who else is involved in the decision making process?” Another bold question is the budgetary question, “Tara, let me ask you: have funds been budgeted for this project (product, service)?” A third bold question is the time frame question, “Wendi, when will the decision to buy be made?”

What are your bold questions? Add them to your Questioning Guide.

Deadly Sin # 7: Assuming that One Person Has All the Answers to Your Questions

Depending on the nature of your sale, there may be several stakeholders that could be impacted. Each stakeholder has different needs and requirements and it is vital that you ask each of THEM questions that are relevant to their situation.

Here’s what you do. First, ask your contact who does this sale affect? Second, use a bold question and ask your contact for the names of those who might have a stake in the sale. Third, create a Questioning Guide for each particular stakeholder.

Deadly Sin # 8:  Not Asking Pain and Gain Questions

Pain questions are those that query about a problem or a predicament or a concern that a client might have that you can fix. Gain questions query about opportunities or enhancements that you might be able to provide. Both questions deal with the issue of motivation. Find a pain or find a gain and you’ll begin the motivation process.

How do you do this? Simply develop a list of questions that pinpoint pain and gain. (Your Question Guide is the place for these.) For instance, “Mr. Gunderson, one thing teachers have been telling us is that creating daily class plans is time consuming and frustration. Let me ask, is this similar to your situation?”

Deadly Sin #9:  Not Asking Questions that Quantify

Uncovering a pain or gain is a good start but it is rarely enough to close the deal. The pain or the gain might be minor at this particular stage and not important for the client to take action. You need to quantify the motivator. Quantify means getting the client to evaluate the nature and extend of a problem or an opportunity. Often they don’t readily see the implications of pain or gain and they need you to help them assess the situation.

For example, you can ask how often a problem occurs. What does it cost the client when it occurs in terms of both time and money? This creates magnitude. The greater the magnitude the greater the motivation.

Deadly Sin # 10:  Not Using Questions to Respond to Objections

The trouble with an objection is that you can never be certain if it is the REAL objection or if it is a false objection. The way to deal with virtually any objection is to a) pause, b) empathize and c) ask a question to determine if the objection is real or if it is hiding something else.

For instance, suppose the prospect objects to price. Ask him to “explain” what he means by price. Does he really mean budget or is it an issue of value or is he comparing apples to apples? Who knows? So use questions to solve objections.

Deadly Sin # 11: Not Listening to the Answers to Your Questions

Perhaps one of the deadliest blunders is asking a question but failing to listen to the answer. Some reps dutifully ask questions but instead of listening they are simply waiting for their turn to speak.

To solve this, stay focused on the words being uttered. Use a pen and pad and take notes because it forces you to concentrate. Next, focus on the tone of voice. The way a client speaks offer nuances that can indicate agreement, disagreement, confusion, indifference, annoyance etc. If you hear something in their voice, ask about it: “Eric, I think I hear some confusion in your voice. Is there something I can clarify?”

Deadly Sin #12:  Not Asking Verifying Questions

The last blunder is failing to ask verifying questions. This is particularly important in the world of telephone sales, lead generation or prospecting. Verification questions are those that seek to determine if the client understood YOU. For instance, after providing some information to the client (e.g., a product description) ask, “Does that make sense to you?” or “Do follow my logic?” or “How does that sound to you?” Then shut up and listen. Gage the response but more importantly gage the tone. These questions will ensure that you are staying on track and more importantly, that your CLIENT is staying on track with you.


Questions are the very best of tools in the selling process. But use them wisely by avoiding these blunders. Does that make sense?

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