75 Best Sales Questions to Close More Deals

Guest Post by Paul Cherry

Have you ever faced a situation where the sale seemed to be just about sealed, only to stall at the last minute? Or you had great rapport with your contact, but at the last minute another influence came in and derailed the whole thing? Or your prospects decide they simply don’t need change right now? How do you make them see the value of your service, not just the price tag? You do it by asking questions that expand your customer’s mindset, which in turn helps him to realize the value of your solution — BUT how will you know what to ask?

Why Do We Ask Questions, Anyway?

More to the point, why don’t we ask enough questions — important questions? Like many salespeople, you may be nervous about asking questions for fear of asking the wrong ones, or worse, getting answers you don’t want to hear. You don’t always know what to ask, and silence makes you even more nervous. You may even worry that by asking the wrong questions, you’ll come across as intrusive — after all, customers don’t want to feel like they’re being interrogated. Perhaps you even feel like you’re imposing on customers, as if you should already know the answer (why, are you a mind-reader?) This kind of thinking actually does more harm than good, disempowering both you and your customer, who’ll end up feeling misunderstood, unimportant, and unlistened to.

A customer, who feels ignored by the vendor from whom she’s seeking help, is a customer who feels powerless, and therefore resentful. Too many salespeople unintentionally create these negative feelings when they shortchange their questions.

Questions Mean Power!

Instead of feeling powerless when it comes time to ask questions, consider this — when you ask questions, you’re actually controlling the conversation. That’s right, questions mean power! Questions make customers think and respond — and asking the right questions will give you the responses you require to provide customers with the right guidance. Even if you don’t get the answer you hoped for, you’re nevertheless engaging customers’ emotions, and that’s half the battle. Customers may justify their actions with logic, but deep down, it’s their emotions that motivate them.

Questions can help facilitate a presentation. It’s not enough just to give your prospect the facts and features of why to buy — it’s important to give him a chance to respond, and to listen carefully to his responses. When you’re the one doing all the talking, there’s an emotional disconnect because the longer you talk, the more likely it is that your customer is tuning out. He may be politely nodding and “mmmhmming,” but the fewer opportunities you give him to respond, the more likely it is that he’s really in “never-never land.” But if you ask the right questions, you’ll snap him out of his half-listening haze and motivate him to respond in ways that will lead to meaningful dialogue between the two of you.

Like all good salespeople, you want to understand your customer’s vulnerability, his need to control his own fate.

You also want to stroke your customer’s ego by connecting emotionally — responding to the specific concerns he expresses. That’s why you must listen to your customer —his responses are crucial to helping you tailor your questions to his needs and goals. Don’t confuse this with manipulation! If you care about your customer as a person and not just as a source of revenue, it will show in the way you ask your questions. The key is to help your customer find his business pain and tap into it. At the same time, good questions can help bring out the positives. You can help your customer feel positive by talking about his strengths, which in turn kick-starts his subconscious into thinking about the specifics of what he needs to do differently to capitalize on those strengths. Aha! Now you’ve planted the seeds where you can begin to position your solution as the possible answer.

We also ask questions to force people to think, therefore tapping into their needs, wants, and desires, getting them on your wavelength, leading you and your customer to think in unison. This process helps you and your customer diagnose the problem and break it down. Only then, can you grasp the magnitude of this problem and any potential negative ripple effects of the problem the customer wants you to solve. The good news is: the larger the customer’s problem, the bigger your solution!

Warm-up Questions With New Relationships

Remember that before you can work with your customer on a solution to his problem, you need to get to know him. While you can’t hurry trust or manipulate a business relationship into a specific timeframe, you’ll find it’s worthwhile to invest time in the relationship-forming process by asking the right questions about the customer’s past and present — and, equally important, being patient and listening to their answers. If you really listen to what your customers have to say, you’ll instill confidence in them, forming the foundation upon which to build a powerful business relationship. Of course, you can ask questions about the weather, sports, weekend or what’s happening in the news. But in addition to those types of questions, it’s good to gain insight on what your prospect is experiencing on the job and the challenges he and his organization are facing. His input may reveal valuable information on other relationships to form in his organization and how best to position your solutions when the time is right.

    1. How long have you been doing _______? So tell me what you like most about _______? Least about _______?
    2. What would you say is different about your organization (project, job, etc.) today compared to when you started _______?
    3. Could you share with me some past experiences with vendors when it comes to _______?
    4. Since you’ve been with the company, what have been some of the challenges you’ve been facing with ________? What originally led you to take on this responsibility (project, job, task, etc.)? What were your expectations when you started, and how have they changed, as you look at your needs today?

Questions to Disrupt Existing Vendor Relationships

Phrase your questions in ways that won’t end up undermining your efforts to win your customer’s business. For example, don’t just ask your customer, “What do you like about your current supplier?” If she’s fairly content with the status quo, she just might start talking about all the positive qualities of that relationship… and if things are going just dandy between them, what does she need you for? Here are better ways to get that information without undermining what you have to offer.

    1. Would you share with me the ideal qualities you look for in a vendor?
    2. When you originally selected this vendor, what were your selection criteria? In what ways have your criteria changed as you evaluate your needs today? What would you like to see happen in the future?
    3. If you could enhance one thing about your vendor’s qualities, what would that be?
    4. How would you rate your current vendor relationship on a scale of 1 to 10? (When your customer states a number, urge her to elaborate, as with the following example.) All right, when you say 7, what would you want your vendor to do to move it to a 10?

Questions to Strengthen Existing Customer Relationships

It’s all too easy for salespeople to take their customers for granted. Oh yes, customers are guilty as well. These questions work best when you already have a relationship in place, but you’d like to take it to a higher level in order to capture more business. About once or twice a year, I enjoy taking my important clients to lunch or dinner so we can reflect on our recent accomplishments working together. My other objective is to explore how our business relationship can improve and how I can add more value in the months (or year) ahead. These questions are asked in a relaxed setting and when there’s time to talk about the big picture. Because you never know if and when your competitors are trying to steal your important clients, I suggest asking a few of the following examples. Be sure to put them into your own words so the questions are conversational. Ask these types of questions, and you’ll turn good relationships into great ones:

Examples of questions on strengthening existing customer relationships:

    1. What do you feel we are/ I am doing right to sustain our business relationship? (Continue with lots of follow-up questions)
    2. What could we be doing differently (more of/less of or where can we improve) in order to ensure that you achieve your goals?
    3. What’s most important to you for us to keep focused on your objectives?
    4. If you could enhance one thing about our business relationship, what might that be?
    5. In what ways can we make your job easier? rewarding? profitable? successful?
    6. If a prospective customer were to ask you to explain why you do business with us, how would you respond?

Note from Bob:  You have just read 14 of Paul Cherry‘s “75 Best Sales Questions to Close More Deals.”  Good News:  Thanks to Paul’s generosity you can click HERE to download all 75!

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.”


10 Questions to Ask Your Mom or Grandma on Mother’s Day

My Mom, Clara Tiede, was the best Mom I could have ever had.  With one year of Junior College she became a...

5 Questions for Helping Others with their Struggles

Guest Post by Dr. K. Shelette Stewart A few years ago, when I resigned from my leadership role at Harvard...

4 Best Icebreakers For Team Meetings

Guest Post by Dr. David Burkus Originally posted @ DavidBurkus.com Icebreakers are not just games or...

Do You Have a Hard Time Saying “No”?

Excerpted from Chapter 24 of “Now That’s a Great Question.” Click HERE to listen to Chapter...

Four Words

Excerpted with the permission of the authors from Chapter Three of Power Questions: “Four Words. ...

You need Questions…. Not Answers….Start here

Guest Post by Diana Kawarsky You’re a new hire in financial services, maybe an Analyst or Associate who...

Celebrating the 12th Anniversary of LeadingWithQuestions.com

All this week, we are celebrating the 12th Anniversary of LeadingWithQuestions.com with the release of my...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.