Book Summary of ‘Questions That Sell’ by Paul Cherry

If you want to succeed in sales, you need to get very good at developing true business relationships.

You do that buy understanding their vision for their business, their fears and motivations.

The path to get there is through great sales questions. In one of the greatest metaphors ever employed in a sales book, Paul Cherry calls great sales questions “truth-seeking missiles.”

When you point those missiles in the right direction, you will:

  1. Motivate your prospect to do the talking. Great questions help you get to the insight you need to close deals.
  2. Differentiate yourself from your competitors, who don’t know how to ask great questions.
  3. Demonstrate empathy for your prospects. By establishing yourself as somebody who will listen to problems and frustrations, you’ll create an environment where your prospect will share information they wouldn’t otherwise share.
  4. Facilitate a prospect’s awareness of their needs and help them come to their own conclusions. Your prospect must come to see their problems on their own.
  5. Prompt a prospect to recognise the importance of taking action.
  6. Discover how a particular company makes a purchasing decision, as well as whom the decision makers are within the company.

In this summary we’ll review the 6 types of questions you need to use in order to achieve your biggest sales goals.

Let’s get started.

  1. Educational Questions

Educational questions are designed to enlarge a customer’s knowledge.

Your prospects are cynical – and rightly so. They’ve spent far too many hours of their lives listening to sales reps show up and give dog and pony shows.

One of the best ways you can set yourself apart from your competition is to ask educational questions – by engaging your prospect in sharing information that’s relevant to their problems.

Here’s a template for asking an educational question:

“I read recently in an article from ___________ that ___________ . Tell me, how does that compare with what you are seeing?”

For example: “A recent article in the Wall Street Journal suggests that 75 percent of technology companies use foreign developers to build out their platforms. One of the challenges seem to be the language barriers and laws governing foreign workers. How do you manage those issues with your IT staff?”

When to Use an Educational Question

There are 4 situations where an educational question will be very helpful:

  1. As a teaser on a voice mail to get prospects to return your call;
  2. At the beginning of a meeting to use as an icebreaker;
  3. When a sales conversation is stalled;
  4. When you want to breathe new life into an existing customer relationship.

Just make sure not to overuse this strategy. Cherry suggests that one educational question per meeting is enough to be viewed as a consultative seller.

  1. Lock-On Questions

Lock-on questions build on what buyers have told you, which allows you to extend the conversation and dig deeper into the issues they face.

The trick is to lock on to something that you believe will give you – as well as your prospect – greater insights into their real needs.

Here are a few examples:

If your prospect says “We have been trying to get this project launched for months now”, you might follow up with “I noticed you used the word trying. What has worked so far and what’s standing in your way?

If your prospect says “I’m looking for a partnership rather than a vendor who is just looking to peddle a product”, you might follow up with “Can you give me a little more insight into what you mean by partnership?”

If your prospect says “We’ve had a bunch of problems with our current vendor and we are looking for a new supplier”, you might follow up with “Can you share some of the specific problems you’ve been having?”

When to Use Lock-On Questions

One of the things to be aware of when you start using lock-on questions is that you run the risk of the prospect feeling like they are being cross-examined if you get too aggressive with them.

So, make sure that you use lock-on questions when the following conditions are true:

– You have good rapport with the prospect and you have demonstrated empathy toward them.

– You have a sincere desire to connect with the prospect.

  1. Impact questions

Impact questions are designed to explore the impact of the challenges the prospect is facing.

Once the prospect has articulated a problem that needs solving and gives you an example, it’s time to use that information to get the prospect to focus on the impact of the problem.

This is not an easy process, but the results are worth their weight in gold.

You are giving the prospect an opportunity to vent their frustrations (which everybody loves to do), and they’ve also relived their problem again and are now in a state to want to solve it.

There are a number of ways the problem they are facing could impact them. Here are just a few things it could impact:

– the company

– the prospect’s position in the company

– the prospect’s well-being

In most cases, customers have never taken the time to deeply analyse their problems, or calculate just how much it might be costing them.

With that in mind, here are some of the ways you might phrase the impact questions to get the wheels turning:

“What do you think the impact on your company will be if you decide to do nothing?”

“What impact do you think this problem could have on you within the company?”

“When you have this problem, how much do you think it will cost you to fix it?”

“How much time do you spend dealing with this problem on a daily basis? What else do you think you could accomplish if you got that time back?”

Once they start articulating the problem, they’ll probably start mentioning how it affects them personally. A common frustration is a problem at work taking them away from their family on nights and weekends. If that comes up, you might say something like:

“You mentioned losing time with your spouse and kids. Do you think that will change if the problem continues?”

If you can get your prospects to do a deep dive on how much their issues are costing them, they’ll come to the conclusion on their own that they need to fix it.

  1. Expansion questions

Expansion questions are designed to get buyers to enlarge on what they’ve already told you, giving you greater insight into their needs.

The idea here is that the more you get prospects to reveal, the more likely they are to buy from you.

For instance, if your customer gives you a story, or reveals their thought process, or gives you a peek into how their company makes decisions, the more likely you are to gain insight into how you can help them.

These types of questions begin with phrases like:

“Describe for me . . .”

“Share with me . . .”

“Explain . . .”

“Walk me through . . .”

“Tell me . . .”

“Could you clarify something . . .”

“Can you expand upon what you just said?”

“Help me understand . . .”

Here are some sample questions transformed from ordinary questions into expansion questions.

Ordinary questions like: “Who is the decision maker?” “When will you make a decision?” “What is your time frame?”

Turn into expansion questions like: “Walk me through your company’s decision making process.”

Ordinary questions like: “Are you satisfied with your current system?”

Turn into expansion questions like: “Share with me your level of satisfaction with your current system.”

Ordinary questions like: “Is price important to you?” “Is quality important to you?” “Is service important to you?”

Turn into expansion questions like: “Explain to me the criteria you use to ensure you’re getting the best value.”

  1. Comparison questions

Comparison questions get buyers to compare one thing to another. This is a very useful tool for getting more clarity on your prospect’s priorities.

These questions open up many avenues for discussion, including:

– Time: what has happened in the past, what is likely to happen in the future and how priorities might change over time.

– Decision makers: these questions let you figure out who makes the big decisions in the organisation.

– The prospect’s competitors: these questions can stimulate a dialogue about your prospect’s industry and how they differentiate themselves from their competition.

– Alternative choices: you can open the door to new solutions your prospects might not have considered before.

Here are some examples:


Ordinary questions like: “What are your goals?”

Turn into comparison questions like: “Share with me what you hope to accomplish in the next twelve months compared with where you were one year ago.”

Decision makers

Ordinary questions like: “Who will make the final decision on this?”

Turn into comparison questions like: “Please explain to me how the decision making process for this project differs from past projects you’ve worked on.”


Ordinary questions like: “Who are your competitors?”

Turn into comparison questions like: “Your customers have a lot of choices today. Tell me what you believe are the unique attributes that set you apart from others in your market.

Pains and gains

Ordinary questions like: “Tell me about what’s not working.”

Turn into comparison questions like: “Compared with what you’ve seen in other organisations where you’ve worked, explain to me the gaps you see in your current organisation.”

Market trends

Ordinary questions like: “How’s business?”

Turn into comparison questions like: “How’s business this year compared with last year?” Or, “How is your business compared with others in your industry?”


Ordinary questions like: “What do you like about your current vendor?”

Turn into comparison questions like: “Describe for me the ideal qualities you look for in a vendor relationship and how that compares with your current situation.”

The point of asking these questions is that the answers come with information you can use as you determine exactly how you can help the prospect.

  1. Vision questions

Vision questions invite your prospect to see what they stand to gain through doing business with you. Ultimately, you want your prospect to come to the conclusion that you can help them achieve their goals, hopes and dreams.

Most vision questions have the word “if” in them. For example:

If we could eliminate that problem you have – the one that is costing you $2 million per year, what would it mean to you and your organisation? What would it mean for you personally?

Your prospects will usually freely share their explicit needs – things like cost savings, creating market share, and profitability.

But in order to truly get your prospect to open up about what they really want – their hopes and dreams – you need to understand their implicit needs.

They can be broken down into 7 categories:

  1. Success. This is the need to feel a sense of accomplishment when they come home from work. Prospects who often talk about wanting to “get the job done” or “earn more money” usually want to feel successful.
  2. Independence. This is the need to feel in control at work. Prospects who talk about wanting their bosses to trust their decisions are usually looking for the feeling of independence.
  3. Recognition. This is the need to feel valued as a team member. Prospects who talk about all the hard work they do, or about wanting people to listen to their ideas, are usually looking for recognition.
  4. Security. This is the need to feel like your job won’t be taken away from you, and the need to not look stupid in front of their team. Prospects who use words like concerned, worried, unsure and doubtful are often looking for a feeling of security.
  5. Stimulation. This is the need to feel challenged by your job. Prospects who talk about tasks they dislike doing or that all they do is “put out fires” are typically looking for a feeling of stimulation.
  6. Peace of mind. This is the need to feel like your areas of responsibility are taken care of. Prospects who ask you very tactical questions and seem concerned with deadlines are usually looking for peace of mind.
  7. Simplicity. This is the need to feel like life is easier. The more you can make your prospect feel like you will take care of their problems, the more they will have the sense of simplicity in their lives.

Asking questions that will allow your prospect to realise that their implicit needs will be met by doing business with you is the ultimate victory.


When you are able to ask the 6 types of questions you need to ask in order to get the prospect to envision a brighter future by working with you, there will be no limit to what you can do!

P.S. I need a business coach (willing to train [at my expense] the right individual with some get up and go / sales/ marketing prowess) to facilitate demand for my coaching business. If you, or someone you know, is interested, please click for more informationScreen Shot 2018-03-27 at 10.51.23

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