Introduction to Questions that Sell

If we are good at anything as coaches, we are masters of asking effective questions. What if you could use your superpower of asking excellent questions to help you sell your services better, faster, and cheaper? This book summary, “Questions That Sell” by: Paul Cherry, helps give us some guidance on what questions are best for selling.

Questions that Sell Book Summary

If you want to succeed in sales, you need to get very good at developing true business relationships. To do this, you must understand your customers’ vision for their business, their fears, and their motivations. 

The path to developing true business relationships is to ask great sales questions.

In one of the greatest metaphors ever employed in a sales book, author 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 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 their problems and frustrations. In doing so, you’ll create an environment where your prospects will share information they wouldn’t share otherwise.
  4. Facilitate a prospect’s awareness of their needs and help them draw their own conclusions. Your prospect must come to see their problems on their own.
  5. Prompt a prospect to recognize the importance of taking action.
  6. Discover how a particular company makes a purchasing decision, as well as who the decision-makers are within the company.

In this summary, we’ll review the six types of questions you need to ask 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 base. 

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

One of the best ways you can set yourself apart from your competition is to ask educational questions by engaging your prospects to share 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 seems 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 four situations where an educational question would be very helpful:

  1. As a teaser on a voicemail 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; or
  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.

2. 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 want to 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 several 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 prospects feeling like they are being cross-examined. It can come across as being too aggressive with them.

To avoid this, use lock-on questions when the following conditions are true:

  • You have a good rapport with the prospect and have demonstrated empathy toward them.
  • You have a sincere desire to connect with the prospect.

3. 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, so they 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 examples of what could be impacted:

  • 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 analyze their problems or calculate just how much it might be costing them.

So, 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.

For example, 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 into how much their issues are costing them, they’ll come to the conclusion on their own that they need to fix it.

4. Expansion questions

Expansion questions are designed to build on what a prospect has already shared with you by providing 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 tells you a story, 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 such as:

  • “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 such as:

  • “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 such as:

  • “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.”

5. Comparison questions

Comparison questions allow 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: Helps you determine 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 help you figure out who makes the big decisions in the organization.
  • 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 12 months compared to 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 organizations where you’ve worked, explain to me the gaps you see in your current organization.”

Market trends

Ordinary questions like: “How’s business?”

Turn into comparison questions like: “How’s business this year compared to last year?” Or, “How is your business compared to 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 to draw information from your prospects and to use that information to determine exactly how you can help them. 

6. Vision questions

Vision questions invite your prospects to see what they stand to gain through doing business with you. Ultimately, you want your prospects 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 organization? What would it mean for you personally?

Prospects will typically share their explicit needs freely, which includes things such as 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.

Implicit needs can be broken down into these seven 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 prospects feel like you will take care of their problems, the more they will have a sense of simplicity in their lives.

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

When you are able to ask the six 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.

*** End of Book Summary ***

Now, as a coach, you know that just reading this book summary does not help you get from where you are to where you want to be. You need to decide what information you learned in this post that you can use immediately to take action. That is why I like to provide the nanocourse for you after the book summary.

Selling Through Coaching Questions

Proof: This playbook is inspired by “Questions That Sell” by Paul Cherry. While the book targets sales professionals, its principles are incredibly relevant for ICF professional coaches. The art of asking the right questions not only facilitates transformative coaching but can also be a powerful tool in selling coaching services. By drawing parallels between coaching questions and sales questions, coaches can effectively communicate the value of their services.

Principle: The foundation of successful coaching and selling coaching services lies in understanding the client’s or prospect’s vision, fears, and motivations. By asking insightful and targeted questions, coaches can uncover the true needs and desires of their clients or prospects. These questions, akin to Cherry’s “truth-seeking missiles,” not only provide valuable insights but also position the coach as a trusted guide, both in transformative sessions and in selling their coaching services.

Promise: By mastering the art of asking the right questions, both in coaching sessions and in selling your services, you’ll foster genuine connections, differentiate yourself from other coaches, and increase your client base. This approach will position you as a trusted partner, making clients and prospects more open to the transformative power of coaching.


  1. Educational Questions: Begin by expanding the prospect’s understanding of coaching. Say, “I’ve learned from XYZ that effective coaching can lead to ABC. How does that align with what you’re seeking in personal or professional growth?”
  2. Lock-On Questions: Build on what the prospect has shared about their challenges or goals. If they mention a desire for change, ask, “You mentioned wanting a change in your career. Can you share more about what’s driving that desire?”
  3. Impact Questions: Explore the ramifications of the challenges or desires expressed by the prospect. Ask, “How do you see your current challenges impacting your future aspirations?”
  4. Expansion Questions: Delve deeper into insights already shared. Transform ordinary questions into more insightful ones, such as changing “Why are you considering coaching?” to “Can you share more about the experiences or feelings that led you to consider coaching?”
  5. Comparison Questions: Allow the prospect to compare their current situation to a past or desired future state. Instead of asking, “How do you feel about your current job?”, ask, “How does your current job satisfaction compare to previous roles?”
  6. Vision Questions: Encourage the prospect to visualize the benefits of coaching. Ask, “If through coaching, you could address and overcome these challenges, what would that mean for your personal and professional journey?”

Prompt: Reflect on a recent conversation where you were introducing your coaching services to a potential client. Which types of questions did you employ, and how did they influence the prospect’s perception of the value of coaching?

*** End of NanoCourse ***

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