Skip to content


July 11, 2019

Written by Ari Greenbaum, co-founder of conXpros


I must confess. In my previous blog article,  We Have Two Ears and One Mouth So We Can Listen Twice as Much as We SpeakI made it sound as though all you must do is “tune in” and the prospect will gladly provide you with a detailed treasure map to the buried “yes”. If this was the case, everyone would be a superstar, as long as they worked on and became an excellent listener. In reality, you must elicit the information from your prospective buyer and then you can utilize the skill of listening. I employ the concept of “don’t ask, don’t tell” in my selling process when trying to engage a prospect; if YOU do not ask, they rarely will tell. For this reason, asking questions is closely connected to the skill of listening. To become a successful sales pro, you must learn and work on your ability to ask the right questions and at the right time. This skill allows you to control the direction and flow of the selling process. Generally, a conversation between two or more people consists of a series of questions and answers, with the one asking the questions in control of the conversation. I used the term conversation, because that is an additional benefit of question asking. Doing such allows you to engage the prospect as opposed to speak at them or find yourself in a monologue. Your ability to be conversational in your sales approach as well as your ability to maintain control will be a dominating factor in successfully guiding your customer to agreement.

There are additional benefits and positive impacts gained when you engage in asking your potential buyer questions. When you are asked questions by another person, how do you feel? Typically, when being asked questions you will feel that you and what is important to you are also important to the person asking. There is no better way to broadcast your interest in someone than to ask them questions, especially about them! This also will help you to establish report and more importantly trust with the prospect. You show them that you want to understand their needs and who better for them to trust in meeting their needs than the person expressing a clear interest in doing exactly that. Beyond gaining clear understanding and making these strong connections with someone you desire to do business with, you gain their attention. When you are speaking, you will only command a small percentage of the prospect’s attention. They will be focused on countless other things filling their conscious thought at the same time you are sharing valuable information. If you want them to focus 100% of their attention on you, ask them a question! They want to be able to answer you and to do so requires complete focus on what is being asked. What better scenario could there be for you as the sales pro, than to have 100% of your prospect’s focus and attention directly on you?

Questions can be used to help you in many different ways. You will use questions to build trust, report, give the feeling of importance to the prospect, and show an active interest in learning and understanding their needs. You can also use questions to gauge the interest level of a prospect through trial closes, or questions intended to “take the temperature” of their readiness to move forward in agreement to do business. You can use hypothetical situational questions in the closing process to take the pressure off of the customer from “making a real decision”. Questions can also be used in the form of “nail downs” that help guide the prospect towards a positive answer. Regardless of the types of questions you are asking or using, you must first understand some critical application points of how to successfully use this powerful tool. I like to use the analogy of a chess who anticipates all potential countermoves to their move BEFORE they make them. When you ask questions, you must do so with this same level of clarity. Random, thoughtless, and non-prepared questions will result in the opposite results that you desire. Like the chess player, you must be able to anticipate the potential answers to the questions BEFORE you ask them. This is not to suggest that you should limit yourself to closed ended questions as they have only a few potential responses, but if you are predetermined in why and when you are asking the question to the prospect, you can predict with little variance the possible responses. I never ask questions that I do not “know” or are able to anticipate the potential answers before asking. This skill can only be accomplished through practice. Unfortunately, there is no other way to predict responses or have clarity and purpose behind every question you ask unless you put the work into thinking about and playing out every possibility in your mind. This is no different than the chess player who studies all potential moves and the additional moves that follow many steps removed from the starting point before they ever sit down at the table to play the game. You must develop a library of questions and the potential responses and know based on each response exactly what your next “move” will be. What I just described is Clarity of Thought and Speech at a superior level. When you can turn selling into an art form and flow naturally in conversation guided by your questions, you reach mastery. Trust me, you will experience tremendous levels of success preceding the mastery level, which will have a direct impact on your ability to close more sales, but being a master is a ton of fun!

Below, I will provide a breakdown of how asking questions applies to each of the 3 phases of the selling process: discovery, presentation, and addressing objections & concerns

Discovery/Interview stage: All stages of the sales process are important, but none as much as the discovery and interview stage. The customer will either be engaged or not in this stage and thus requires great care and effort to make the proper impression on and connection with the person you are speaking with. When possible, you should know as much about your prospect and what they do BEFORE entering the sales process. The more prior knowledge you have will allow you to not only show them that you are interested in them and their business, but also that you are a pro they can rely on.  Of course, not every selling environment allows for this approach, but when possible, it is a must. Throughout this stage, you must avoid talking about your product or service’s features or benefits. You will have plenty of time to tie features and benefits to your prospects needs in the presentation stage, but you want this stage to be COMPLETELY about them. You want to approach the discovery in a flowing and conversational manner to avoid the “interrogation” feel. Nobody likes feeling interrogated, but everyone likes to speak with people who are genuinely interested in them. Conversational flow combined with the proper types of questions create this feeling. Your questions should predominantly be open-ended questions, ones that allow the customer to answer without being “fed” or guided to a particular set of answers. You can also sprinkle in directed questions and a few closed ended questions when appropriate, but try to stay open-ended as much as possible.

The purpose of all 3 types of questions is to enable you to uncover what the customer’s needs, issues, and pain points are. With this in mind, the questions should build on one another based on your agenda or plan to reach your objective. You also establish in the discovery process the needs and gaps (needs-gaps analysis). This fancy term is easily understood by what we already described above to identify the needs of your customer, but adding questions that will help you gain understanding of what is missing and create a clearer target for you to later focus your solution based presentation on, hitting a bulls-eye every time.

Presentation stage: You will use far less questions during this stage of the selling process, but it is important to incorporate a few.  This continues with the conversational feeling you have already established during discovery. It is easy to slip into a monologue when presenting a service whether or not you are using a structured “pitch”. You will want to tell them all about how wonderful your product or service fits their needs and solves their problems. There is nothing wrong with enthusiasm, but you want to show the customer not just tell them. The use of questions will keep them engaged and more tuned into what you are presenting. Remember what I shared above; people are 100% tuned in when they are asked questions as opposed to allowing distractions to take their focus away from all of the valuable solutions you are presenting. Simple questions sprinkled throughout your presentation such as “does that make sense to you” or similar closed ended questions allow this tuned in effect to happen. Additionally, when the opportunity presents itself, you can also use “nail down” questions. However, remain conscious to not overdo them as they tend to come off somewhat “salesy” when overused. These are questions such as “I am sure you can see how (feature/benefit of your product or service) will help meet (the specific need), correct?” Remember to not overuse them but fit them in when you have made a major point in your solution to meet their needs.

Addressing objections & concerns (post presentation): There are many sales trainers and authors who suggest that you must have a practiced response or rebuttal for any possible objection or concern. There are many that have books dedicated specifically to this approach. I am not suggesting that these approaches are wrong or ineffective, as I also suggest having an arsenal of rebuttals. The problem is that often salespeople forget there is a critical step before rattling off a canned response to the concern or objection of a potential buyer. You must first understand the objection and what is motivating your prospect to make the statement before you can effectively overcome it. In this stage, you must focus on asking questions that are designed to uncover the “core” issue or factor for their hesitation. I also refer to this as understanding the “why”. You must uncover what is causing the issue and thus avoid putting a “band-aid” solution on the problem. If you visit a doctor with congestion and a cough, the doctor does not suggest picking up some cough syrup and getting some rest, rather they do a thorough examination intended to find what is causing your symptoms and provide treatment for the cause. Just like a doctor does not treat the symptom, so too you as the sales pro must identify the cause and treat the source. This is where questions become your “examination” tool.

Another important use of questions when addressing concerns or objections is to move the prospect down a “paved road” I suggested in my blog post on clarity and conversation. To successfully pave the road, you must use guided questions which have limited possible answers. This is what I earlier likened to a chess player, where you know the possible responses to the questions you ask before you ask them and based on the responses, you follow up with more questions guiding them towards the close. This is best accomplished by starting very general and moving narrower towards the close based on logic. The questions must be geared towards bringing the issues to the surface, understanding the needs, and then tying the features or benefits of your product or service that provide the “treatment” for the issue. There is an analogy to visiting a dentist which I offer to better understand this concept. If you have ever visited a dentist for something more than a cleaning, such as the extraction of a tooth, you will easily relate to this scenario. Even though the dentist is aware of the reason for your visit (tooth extraction), they do not just get to work on the procedure upon your arrival, rather they follow a process designed to reduce the emotional “pain” the visit has potential to inflict. They will first ask how you or your family are, what is new, etc., then they provide an overview of the procedure they will be performing, and begin with what they just described. They slowly lean your chair back, give you the first numbing topical gel, then only after you can only feel pressure, but no pain, do an injection which causes you to go completely numb and require the suction straw to prevent drooling. At this point you would not feel any physical pain if they simple yanked the tooth right out of your jaw, but still they slowly wiggle the tooth back and forth until it is extracted. As I pointed out, this is mainly done to diminish the emotional pain as for many hours after the procedure is complete you still cannot feel anything. The dentist knew exactly what the problem was as well as the solution for it, yet they chose to start very general and work their way in a narrowing manner towards the predetermined solution. Solving a customer’s problem can either be painful or pleasant. Taking the same general to narrow approach to discovery, identification of the issues, and solutions to the problems, paves the road to your success at extracting the “yes” from your prospect.

Asking questions is an essential and powerful part of closing, regardless of what stage you are at in the process. The key is to practice the questions so you ask them effectively, play out scenarios based on the potential answers you may receive to “know” the answers before you ask, and learn from your experiences through self-awareness and self-assessment. When you master the art of asking questions, you will identify the needs, issues, and pain points of your customers while maintaining the conversational feel and show your prospect that you are truly interested in them. Never be afraid to ask. You cannot receive an answer if you do not ask the question.


Looking for more information? Send us an email and we'd be happy to answer any questions you may have.

Please enter a valid email address.
Please enter your first name.
Please enter your last name.
Please enter a valid phone number.
Please enter your company name.
Please select a primary trade.

By clicking 'Get Leads', you authorize conXpros to call or text you on the phone number provided using autodialed and prerecorded calls or messages. Your consent to this agreement is not required to purchase products or services. We respect your privacy.

An error occurred, please try again. Your request has been blocked by your browser.