The 4 Kinds of Sales Discovery Questions to Drive Your Prospects’ Interest

4 people solving a problem maze through 4 types of sales discovery questions
In a recent post, we explored the potential of enhancing the evaluation stage of the sales process by asking relevant sales discovery questions. In this post, let’s take a deeper dive into how your salespeople can use the questioning process to build their credibility while increasing interest on the part of their buyers.

The 4 Classes of Sales Discovery Questions That Allow Your Team to Build Credibility and Trust While Gathering Information

In the other post on questions, we used a river analogy as a blueprint for developing a questioning model. In this river analogy, one bank represented the buyer’s current situation. The opposite bank represented the desired situation. And the river represented the gap that the buyer must bridge in moving from the current situation to the desired situation.

When we think about the analogy of this river model, we see that our sales discovery questions fall into 4 types of questions that allow us to develop a questioning process and a sales strategy that not only gathers the information salespeople need but also gives them credibility and builds trust on the part of the buyer. These four types of questions are::

  1. Current situation questions which tell your salesperson where their buyer is now
  2. Desired situation questions which identity where the buyer wants to be
  3. Challenges and opportunity questions which helps the buyer see what’s stopping them
  4. Payout questions which helps the buyer see the reason for bridging the gap.

In this session, we’re going to hold to developing this questioning strategy for discovery in the sales process. We won’t go into a lot of detail about the benefits of open-ended sales questions over close-ended sales questions. This is an opportunity for your salespeople to use all forms of questioning to discover as much information as possible about these four categories from their buyers.

As I mentioned before, one of the jobs your salespeople must perform is to act like a big bottle of Windex. They want to bring clarity to the situation their buyers are experiencing, and help the buyer become aware of all aspects of the pain points in their current situation.

Use Sales Discovery Questions to Identify Your Prospect’s Current Situation

Let’s start with the first class of sales questions which essentially ask, “where are you now?”

One of the things a sales rep’s discovery questions must do in the evaluation stage of the sales process is to identify and highlight the prospect’s current reality and the events that got them there. When your sales reps are highlighting the current situation, they are asking sales discovery questions or using phrases like, “tell me about your company. Tell me about your role. Tell me about what brought you into the store today.”

Your sales reps’ goal here is to perform a thorough examination of all aspects of the buyer’s current situation. And they need to do this while getting the buyer to understand all the factors that have led them to this situation, especially the challenges they may have overlooked or ignored. The sales questions here open up potential opportunities for their buyers to increase their business performance by saving time, increasing quality, or reducing overall cost of doing business.

An Example of the Sales Questioning Process in Action

Let’s look at an example. Let’s say you are going to your favorite business tech store to buy a new business class router for your small business. You currently have a router that performed flawlessly when you purchased it for your small business three years ago. But as you know, technology changes, sometimes faster than we like. In addition, your business grew over that three year period. You added four salespeople. And with that business growth comes changes in your business environment which you now must  address.

Now, when you first enter the store, most sales reps will start off with pleasantries and then move into determining the need. In fact, most sales reps will start the conversation with “Can I help you?” [A failed sales-opener which we addressed in another post].

After that initial opening, your average salesperson will start promoting products or services as soon as possible. They’ll ask questions about the specs of your current router. They’ll ask if it’s still functional, a question that identifies the level of urgency and reveals who has the leverage in the relationship. They may even ask questions about the router’s current usage, what you liked about it, and how much are you looking to spend. Their goal here is to identify the pain points, find  something you are comfortable with, and then sell you something similar with maybe a few more bells and whistles to sweeten the deal.

An Example of a Sales Hero Executing Her Sales Questioning Process

But let’s say, for today, our salesperson is a real sales hero, Terri the sales tech. She starts the questioning process by asking similar sales questions about your current situation in general, just like the average salesperson. She’ll ask about your current router’s specifications. She’ll inquire about the brand of your current router. She will ask if it is currently functional, again that question which identifies the level of urgency. She’ll ask about its usage patterns.

But this salesperson will eventually dig deeper than the general inquiries. She’ll ask you discovery questions about things you haven’t considered, such as:

  • If you purchase the current router yourself
  • If you currently have an IT person to handle these purchases.
  • if your IT person or network consultant made a router recommendation.
  • Why they aren’t  here researching and buying this equipment for you
  • What kind of environment your current router is installed in, who set up your current network and if they will be integrating this equipment into your environment
  • What has your company’s growth been since you originally acquired the router.
  • About how many users you have and how they are using the network

Her sales questions don’t just focus on the router because this salesperson isn’t just trying to sell a router. She’s asking sales questions about your entire business environment, the users, the end customers, and how you and your team plan to use the router. She’s teeing you up to sell you an entire solution to address your challenge and eventually take you to where you want to go. To refer to another standard sales analogy, she recognizes that buyers buy drill bits not because they want a drill bit, but because they want a hole. Her job is to learn not just about the hole, but also about why you want the hole.

Good Sales Discovery Questions Diagnose The Current Situation While Building Trust and Credibility

So, in response to all of these sales discovery questions our hero salesperson is asking, you explain that your router is having trouble handling your current day-to-day traffic. In addition, you want to add a few more employees, but you know that’s going to increase your internet traffic and that will exacerbate the problems your team is currently experiencing. And the members of your current team are already blaming the “slow internet” for why they can’t make calls, send out emails, and get business done.

Now this is important. Because she is a sales hero, Terri uses her sales questions to create a sales conversation that builds trust while gathering extensive information on your current situation. She uses open-ended questions to allow you to free-form ideas. She uses close-ended questions to narrow the scope when needed. And she uses multiple choice, forced-rank questions to get a sense of what’s important to you and a sense of your priorities. You see, it’s not about using one particular type of questions over another. Your sales reps have to be free to use all the tools they have as the sales conversation develops to learn about their buyers’ current situation while instilling a sense of trust in the buyer and building their credibility.

And that’s key. Your salespeople must adapt to the situation at hand and use their sales questions not only to gather a preponderance of information to build their case, but also to start building their credibility, earning the buyer’s trust, and map out the buyer’s entire current situation.

Good Sales Questions Will Identify the Prospect’s Desired Situation


salesman discovering how to get from current situation to desired situation

After mapping out as many of the details as possible about the buyer’s current situation, your salespeople will next map out where their buyers want to be. This is the part where your salespeople help their buyers envision the future where their problems are solved, and opportunities are made.

Let’s go back to the example where our sales hero, Terri the tech salesperson, is selling you a business class router. When you initially went in, you had an idea of what the problems were and that simply getting a new router would solve your problem. But our sales hero helped you look at all aspects of your environment through her very extensive questioning. This opened your eyes to some of the other challenges you were facing and got you thinking about new possibilities for the future.

So now our sales hero is asking about the future where you have the problem solved. She is asking future oriented questions around identifying and achieving your desired outcome and opportunities. These are going to be discovery questions like:

  • What are your growth plans for the next year or two?
  • What will your business focus be in that timeframe?
  • How many employees do you plan on having in the near future?
  • What activities do you envision your people doing to build your book of business?
  • Do you plan on supporting your own technology inhouse or do you want to keep your people focused on your core business?
  • What if there are other options that will allow you to bring more people online? Would that be a viable option for you?

Good Sales Discovery Questions Will Turn Your Salespeople into Trusted Consultants

Again, you can see variety in the types of sales questions, just like before. And these questions focus on your future plans, goals, and growth. But something else is taking place here. Our sales hero has built up a reservoir of credibility with the depth and scope of her questions about your current situation. As a result, you begin to feel at ease sharing your future plans with her. Our sales hero seems less like a sales rep trying to pitch products or services and more like a trusted consultant helping you plan. And we feel more at ease making larger capital purchases when we deal with someone who comes across as an inquisitive expert with a vested interest in our success.

This is why I don’t like to focus on a cookbook sales methodology that says “use only open-ended questions to get the buyer talking.” Your salespeople need to meet the situation with every tool at their disposal. That includes:

  • open-ended questions that allow the buyer to free form ideas
  • close-ended questions, which help quantify information
  • multiple choice questions which allow ranking and prioritizing
  • essay questions which can put the buyer in a particular situation or environment
  • true-or-false questions which help shape and guide the sales conversation

Your sales reps want to be like our sales hero and use their questioning process  to thoroughly examine and construct their buyer’s future. When they use this investigative approach, they build more credibility and trust on the buyer’s behalf. And that trust renders the buyer open to talk easily about their future goals, growth, and expansion. Your sales reps’ job, in the questioning process, is to sit on their buyer’s side of the table and paint as clear a picture as possible of that buyer’s desired situation that will give them what they really want.

Remember, no one buys a quarter-inch drill bit because they want a quarter-inch drill bit. They buy a quarter-inch drill bit because they want a quarter-inch hole. Your salespeople’s questions should be geared towards identifying what having that quarter-inch hole will give them.

Who Is The Questioning Process For?

In that other post, we reviewed who the questioning process is really for. Most sales reps believe the questioning process is for them so they can identify products or services  to fill the requirements. In fact, we hear that a lot in some of our onsite training sessions.

But as we pointed out, the questioning process is really for the buyer or prospect. They should be central to the sales rep’s questioning process.

Remember, sales is an away game. It takes place in the mind of the prospect. And that’s where your questioning process has to take you – into the mind of your prospect.

We’ll come back to that in a bit. But first, let’s further examine our model through the lens of another example.

A Financial Services Example to Examine the Sales Questioning Process

As we move forward in the questioning process, let’s shift gears and have a look at it using another example. This time, our hero is in the financial services industry. Let’s say we are starting our career and we are finally seeing a sizable chunk of change for the first time in our lives. Our first move, right after the celebration and party, is to visit Fred the financial services guy.

Fred sits us down, and after a brief introduction and sales pleasantries, he starts by asking about our current situation. “So, how long have you been working? Do you have a budget? How much of your income are you currently saving? Are you currently using any financial instruments like a 401(k) or a CD? Are you currently working on your nestegg? Tell me a little bit about what your philosophy is on how you put money away for your future.

After thoroughly examining your current situation, Fred then bridges to the desired situation, a desirable future. “Let’s look at your future. You’re thinking about retirement. What should it be? What are you looking to do? When are you looking to retire?” And so it goes until Fred has a thorough map of where we are and where we’d like to be.

Acknowledging the Gap in the Sales Questioning Process


sales rep's hand drawing bridge for customer to cross the gap

Now when Fred asks these sales questions, like our previous sales hero, you’ll notice two things. First there is a flow from the general to the specific. Remember, the purpose of the questioning process is to build credibility and trust. That trust comes when our sales heroes show us that they do care about our experiences and challenges. They do this by starting off with general questions about our situation. And as the dialogue proceeds, we feel more trusting towards the salesperson and willing to share more detailed information. This opens the door for the salesperson to ask questions that probe deeper into our situation or may be a bit more challenging.

You typically see this when a salesperson asks about a buyer’s budget early in the questioning process. When this question is asked too early, the buyer always has some hesitancy about sharing their budget with the salesperson. But if the salesperson brings up the question of budget much later in the questioning process, the buyer is more likely to come up with creative solutions for overcoming any budgetary challenges. Buyers must know that the salesperson cares more about solving their challenge than making a quick, transactional sale.

The second thing you’ll notice is that our sales heroes ask sales questions in a way that highlight the gap between where the buyer is and where the buyer wants to be. Making the buyer aware of this gap between their current situation and their desired situation is the leverage that drives the sale. The greater the gap, the bigger the opportunity.

But remember, there’s a reason that the gap exists. Most of the time, the buyer is unaware of all the obstacles standing in their way. Your salespeople must bring awareness of the gap and its obstacles to your client. If there were no obstacles standing in your prospect’s way, then moving from their current situation to the desired situation would be simple, they would have achieved their desired situation already, and there would be no need for your salespeople’s help.

Asking Sales Discovery Questions to Bridge the Gap

So, you see that your salespeople need to use their questioning process not only to identify their buyer’s current situation and desired situation, but it also has to make their buyers aware of the gap and the obstacles that live there. Just as our sales heroes examined our current situation and the desired situation, their questioning process brings those obstacles out of the cloudy murk in the gap and into full daylight where they can be identified, examined, challenged, and resolved.

Let’s go back to Fred, our financial services guy. He’s already gotten us to identify our current situation and our desired situation. And his sales questions have created a disparity between the two, and now we are aware of it. So, his questions will now draw our attention to some things that are standing in our way. Let’s use one of the most common excuses for not saving and say, “I’ve got to meet my bills now, I can’t put 10 percent of my income away.”

And that gives Fred the opportunity to ask us more probing questions, getting us to clarify, examine, and take ownership of the obstacle. Or he can challenge it. For example, Fred might say, “Well, what’s going to ultimately happen if you don’t start saving that amount now?”

And we’ll say, “I’m going to be in a scenario where I’m not where I need to be. I’m going to be racing towards the end and I might run out of time if I don’t start doing it now.”

At the end, Fred might say, “If I’m hearing it right, you’d be comfortable if you had a plan to ramp up how to get toward retirement. So, would you be open to that?”

Good Sales Questioning Will Identify the Ultimate Payout

Our two sales heroes spent a considerable amount of time probing into our current situation, our desired situation, and identifying the obstacles that live in the gap between the two. Now, most salespeople will stop here and begin creating the proposal for presentation and submission. But there is one more class of questions that our sales heroes use to really bring this process to a strong close. It can be as simple or complex as you want it to be. But it essentially asks the question, “When you finally reach your desired state, what will that get you?”

By itself, the question sounds like it was pulled from a new-age philosopher. But you must remember that this question isn’t asked at the beginning of the questioning process. It comes at the end after your sales reps have asked a battery of questions and have earned extensive trust and credibility.

Examples of How to Identify the Payout When Asking Sales Discovery Questions

For example, if Fred the financial service guy has gone through his questioning process and has identified all the obstacles in the gap. At the end, he says, “If you had a plan that ramped you up for retirement with minimal impact on your daily life, what would that do for you? What kind of difference would it make in your life?” And we would come back with something like, “Well, I think I would have a little more peace of mind and maybe less stress from worrying about my future.

Or if Terri the tech sales hero has walked us through the current situation, the desired situation, and clarified all the obstacles. And at the end of that process, she said, “Hey, we may have a piece of equipment here that will increase your bandwidth, give you some future flexibility, and offer your people protection from outside bad actors while they do their work. I’m kind of curious about what kind of impact this is going to have on your life when you leave the office.” And we may say, “I’m gonna sleep a whole lot better at night knowing that my team is working and protected.”

The payout question always drives back to an emotional response of the buyer. It enables the buyer to make an emotional investment, something that they can lose if they don’t go forward or can gain if they do move forward. So when you use the payout question, be sure you are dealing with the decision maker. And remember, people buy with emotion and justify with logic.

One Last Example of the Sales Questioning Process

Here is one final example of the sales questioning process and obtaining information while building trust and credibility.

Back when I ran a training franchise, I had all my people go through call center training where I trained them to make inside sales calls. One of those people is now my director of technology. He said during one of his calling sessions, he came across a nonprofit organization that wanted to do communication training for 50 of their people. It would be in-house, tailored to their specific needs, and would last several weeks. The only challenge was that he was dealing with an intermediary. She made it clear early on that she was spearheading the project. But the CEO of the organization was the decision maker, and she would not reveal their name.

So, he gathered information about their current situation and their desired situation and did the best he could with the opportunities for bridging the gap between the two. But since he didn’t have access to the final decision maker, he saw that the payout question wasn’t going to work.

We had a deadline of a week to create a proposal for the group and the woman heading the project said that they were looking at several other vendors.

While he was creating the proposal, he had a crazy idea. He cruised over to the organization’s website and did some additional investigative research. And it was there that he not only discovered the decision maker’s name, but he also uncovered her philosophy, her mission statement, and why she was doing the organization’s work. The decision maker had written the answers to the payout question right there on their site.

He recreated the proposal using the decision maker’s mission statement and philosophy as the foundation for the proposal and then wrapped the answers to the current situation, desired situation, and solutions to overcome some of the obstacles they were facing, all while upholding the decision maker’s basic philosophy.

A little over 24 hours after he submitted the proposal, he got a call from the woman who was managing the project. She said, “Pam was really impressed with your capabilities. She wants to do business with your team. When can you start?”

Use Your Sales Discovery Questions to Build a Solid Foundation for your Sales Process

In review, the sales questioning process is your sales reps opportunity to interact with the buyer and build a foundation for the other stages in the sales process. .Your people’s sales discovery questions need to generate interest on your buyer’s behalf by identifying and highlighting the challenges the buyer faces. Your salespeople do this by asking questions that:

  • review their buyer’s current situation
  • highlight their buyer’s desired situation
  • bring awareness to the obstacles in the gap between the two
  • Identify the buyer’s emotional payout

In addition, how your salespeople ask their sales discovery questions will determine the breadth and depth of building credibility, engendering the buyer’s trust, framing the buyer’s  issues, and shaping the buyer’s mindset, ensuring the rest of the sales process proceeds smoothly. Train them to maintain flexibility and ask sales questions like a consultant and they will be more efficient in closing deals and driving business.

You’ll find more sales strategies for executing your sales process in Lance Tyson’s book, Selling Is An Away Game: Close Business and Compete in a Complex World available on Amazon. Get your copy today!