A Few Questions About…Questions

Excerpted from Chapter One of  “Questions That Sell” by Paul Cherry

SINCE THIS IS a book about questions, let’s start with a few:

What, exactly, is a question? Why do we ask them? Why do we answer them? And why are they such a powerful selling tool?

I like to think of a question as a truth-seeking missile. And that’s why a sales strategy that’s built on questioning is so powerful. The best way we can create value for our customers, our companies, and ourselves is to get to the truth. Much time and money is wasted by salespeople trying to sell the wrong people the wrong solutions to the wrong problems.

As we all know, buyers don’t always tell the truth. Sometimes they hold back on purpose—to be polite, to get rid of you, to gain some perceived advantage over you, or to protect themselves. More often, buyers don’t tell you the truth because they don’t know it. They haven’t done the hard work to truly understand their own wants and needs.

We tend to take questions for granted. But if you stop and think for a moment, something very strange happens when we ask a question: We usually get an answer. In fact, it’s hard not to answer a question. People even feel compelled to answer questions when it would be better to remain silent. Consider, for example, the familiar Miranda warning that we all know from police shows: Suspects actually have to be reminded that they don’t have to answer the police’s questions. Yet many do so anyway.

There’s something deeply embedded in the human mind that creates a powerful compulsion to answer questions. If someone asks a reasonable question in a reasonable way, and for reasonable reasons, it’s almost unthinkable to refuse to answer. It would be seen as a rude, almost antisocial act.

All human knowledge starts with questions. Nearly every profession and field of knowledge begins with a question. Detectives ask, “Whodunit?” Journalists ask, “What happened?” Science asks, “How does the world work?” Religion asks, “Why are we here?” Philosophy asks, “What is true?”

Human beings learn, grow, and succeed by exchanging knowledge with other human beings. I believe that questions are rooted so deeply in our psyche because they’re the most efficient and effective tool at our disposal for acquiring knowledge. Good questions eliminate the extraneous and get to the heart of things. They allow us to acquire specific, useful, and relevant knowledge from other people. We don’t have to download all of the knowledge that another person has kicking around in her brain.

But questions can do more than simply transfer knowledge from one brain to another. The best questions create new knowledge. The person being asked the question doesn’t just tell you what he already knows. By considering the question, he discovers something—about his situation, about his values, about his wants and needs—that he hadn’t understood before.

That’s the transformative power of a question-based selling strategy.

Good salespeople use questions to learn something about their buyers.

Great salespeople use questions to help buyers learn something about themselves.

If you can achieve that, it means you can start solving problems that other salespeople don’t even know exist. Even more important, it creates a deep bond between you and your buyer. “This isn’t just someone who can sell me stuff,” the buyer thinks. “This is someone who helps me grow.”

A Hierarchy of Questions Much of this book is about asking deeper questions—questions that other salespeople might not think to ask, or might even be afraid to ask.

There’s nothing wrong with simple, closed-end questions that a buyer can answer with a yes or no—such as, “Did you see an increase in sales last year?” Especially at the beginning of a sales relationship, you need to get some basic information. And simple questions are great for establishing rapport—they’re easy for prospects to answer and don’t seem threatening.

But that’s where many salespeople stop. And if you don’t dig any deeper, you’ll never have more than a superficial relationship with your buyer. Of course, you have to earn the right to go deep with your buyer. It takes time for buyers to trust you enough to really open up. But when they do, you get to the truth. And a solution that speaks to the truth is a solution your customers will be eager to buy.

Good Questions and Bad Questions

Good questions get you closer to the truth. But some questions can lead you astray. They may create the illusion that you’re making progress when at best you’re going in circles. At worst, bad questions will drive buyers away.

Here are some examples:

•​  Leading Questions

“So wouldn’t you agree that quality is the most important consideration?” “Don’t you want a secure financial future?” Questions like these aren’t designed to get the truth; they’re designed to get agreement. We learn nothing and the customer feels manipulated.

•​  Lazy Questions

“What industry are you in?” “Is this your only location?” This is information we could have gotten elsewhere, so questions like these simply waste your buyer’s time.

•  ​Self-serving Questions

“What do you know about our company?” “Did you get a chance to look over the information I sent you?” “Are there any projects I can quote on?” “How’s my pricing?” “Do you have any questions for me?” “Would you like to see a demo?” Although it’s important to qualify and gauge a prospect’s interest, questions like these can suggest that you are more focused on your own interests than your customer’s. Like lazy questions, they can come across as product peddling or poking around for an opportunity instead of focusing on value-added solutions.

•​  Trick Questions

“Which one do you want—the red one or the blue one?” “If I could show you a way to save 25 percent on your costs, would you be interested?” Buyers see these questions for what they are—a gimmick to get them to do what you want.

•  Hostile or aggressive Questions

“Didn’t you have a plan in place in case of a service outage?” “Why do you continue to invest in a program that hasn’t worked?” There’s great value in questions that prompt a buyer to rethink old assumptions or consider new information. But questions that are designed to put buyers on the spot or make them feel stupid—especially in front of others—will prompt buyers to disclose less, not more.

A Plan for Better Sales Questions

One of the key reasons that salespeople don’t ask better questions is because they lack a plan. Sales conversations can be stressful and a wrong turn can be disastrous. So salespeople often fall back on approaches that seem safe. They ask the usual sales questions in the usual way, as if they’re reading them off a list. They hesitate to dig deeper, because then they don’t know where the conversation will go. And they’re eager to move on to the thing they know best: talking about their products or services.

If you have a plan—a set of tools—you can manage the questioning process with confidence. In the chapters that follow, we primarily focus on six types of questions that are specifically designed for sales. We’ll discuss them in greater depth in the chapters that follow, but here’s a quick overview:

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

Example:  “I came across an article in the latest issue of JAMA (The Journal of the American Medical Association).  It mentioned how diabetes is growing exponentially yet patient compliance is not keeping up.  I’m curious as to what you’re experiencing with your patient population and what you’ve tried to address this trend.”

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

Example:  Prospect states, “Let me run this by my boss to see what she thinks….”    Sales person locks on to the verb “run” with the statement, “Glad to hear you’ll share this with your boss.   So tell me, is this something you’re going to recommend?”   The prospect’s answer will reveal with whether they have the confidence, motivation and/or  knowledge to sell your idea or concept to their boss.

3. Impact questions. These are questions designed to explore the impact of challenges that the customer is facing.

Example: “Assuming things don’t change, what might be the impact on you and your business moving forward?”

4. Expansion questions. These are questions designed to get buyers to enlarge on what they’ve told you, giving you greater insight into their needs.  Expansion questions replace the who, what, where, when, why and how openers with descriptive openers such as, describe, tell me, explain, share, help me to understand, walk me through, etc.    They are especially effective in turning closed ended into open ended questions.

Example:  Instead of asking, “Are you the decision maker?” use a descriptive opener such as, “Describe for me your decision making process?”    It now becomes a much more engaging question.

5. Comparison questions. These are questions that get buyers to compare one thing to another—an especially useful tool for identifying priorities and for gaining greater clarity.

Example:  “Share with me your goals for this coming year verses last year.”  or “Tell me how your opinion differs from others on your team.”  Or “What’s changed since we last spoke?”

6. Vision questions. These are questions that invite the buyer to see what they stand to gain, and how you can help them achieve their goals, hopes, and dreams.

Example: “Tell me what you envision your business will look like three years from now?”

Each of these question types is a powerful tool that allows you to engage your buyer on a deep level, while keeping the conversation on track and moving toward a sale. Once you master these six types, they’ll become second nature and you’ll know how to apply them in virtually any sales situation.

And that leads to one more question: Are you ready to start digging deeper with customers and understanding their truths? If so, let’s get started.

Note from Bob:  Not only will Paul’s “Questions” increase your sales success, Paul’s “Questions” will also increase your effectiveness in leading and coaching your staff!  You will want to order “Questions that Sell” today by clicking HERE

Paul Cherry


Paul Cherry is the president and founder of Performance Based Results, which delivers intense customized sales workshops, coaching, and leadership programs to companies throughout North America. He has worked with more than 1,200 organizations, including 175 of the Fortune 500, plus more than a thousand entrepreneurial, small to mid-sized, cutting-edge businesses looking to dominate their niche markets. Paul’s clients typically get 7 times their return-on-investment (ROI) or better. Paul is also the author of 3 Best Selling Books: “Questions that Sell”“Questions that Get Results” & “The Ultimate Sales Pro.”


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