The 15 Best Sales Questions to Ask (Ever!)

Shawn Casemore • No Comment
Posted: June 4, 2021

After years of selling, I’ve distilled a list of the 15 best sales questions, to use as a powerful sales tool.

What are the best sales questions to ask?

Collectively, they provide insights on how to best position your product or service for the best possible outcome … a sale.

Used correctly, these questions move prospects along a journey of sharing needs, wants, and objections.

Failing to use these questions, or asking them at the wrong time, can quickly kill a sale.

Using Sales Questions Correctly


Effective selling isn’t about interrogation.

It’s using a series of carefully placed questions that help the sales professional learn.

Asking a prospect “Why did they agree to meet?” after some informal discussions is a great way to identify quickly what the buyer’s key objectives are. This in turn can inform and determine the direction of your meeting.

Not asking this question often leads to an agenda focused on what the salesperson wants, versus the buyer. It means the salesperson will waste their time and that of the prospect, trying to move the sales discussion forward.

With over 20 years in the business, today I share the list of my best sales questions to ask customers.

I’ve broken down when to use each question, helping you to create a sales script that will allow you to drive each conversation towards the close.

Best Sales Questions to Ask! The Top 15

This first series of sales discovery questions are part of the “Learning” stage. They will help you understand what your prospect wants or needs:

Learning Stage Questions

  1. Why did you agree to meet with me today?
  2. What challenges/issues are you facing with your current solution/product/service?
  3. What have you done previously to address this issue/need?

Once you’ve completed the Learning stage, you’ll move to the “Outcome” stage. These are more open-ended sales questions that will help you position your product or services to satisfy the buyer’s needs or wants.

Outcome Stage Questions

  1. What do you like or dislike about your current solution/situation?
  2. What does the ideal outcome look like?
  3. How will resolving this problem/challenge help you? Your team? Your company?
  4. What are the most important features you’ll need for this to be a success?

Armed with understanding how to best position your product or service for the sale, the next stage is to ask more sales discovery questions to identify and expand the value of the sale.

Value Stage Questions

  1. What impact would our product/service have on your business?
  2. How will you be better off because of using our product/service?
  3. How will our product/service help you better support your customers?
  4. What’s a reasonable return on investment given the benefits of our product/service?

Once you’ve identified the value of your solution in the eyes of your prospect, you need to ask appropriate sales questions to flesh out their decision-making process. This will help you determine the next steps you’ll need to take.

Decision Stage Questions

  1. How will you decide what the best product/service is?
  2. What factors will affect your decision?
  3. Who else is involved in making this decision?
  4. When do you expect to make this decision by?

Now you’ve asked all the questions necessary to move your sale towards a close, you’ll want to consider the “non-technical” questions that will propel your sale forward.

Depending on the technical aspects of your product or service, you’ll want to add in other questions as necessary to understand the specifics of your prospect’s solution.

Sales Questions to Speed Up the Close


In some instances, you’ll want to introduce questions that will help you close the sale before you’ve signed the documents.

These are akin to making a “handshake deal” and create a soft close.

If there are still several unanswered questions from above, or from a technical standpoint, then you’ll want to wait and use these questions once all answers have been shared.

Handshake Deal Questions:

  1. Is there anything else you need to make your decision, or should we move forward?
  2. Other than a signature, is there anything else that’s stopping you from moving forward?
  3. Should we get started and take care of the details later?

The Power of Sales Questions

I’ve often said that listening is one of the most underestimated skills in sales.

Before you listen, you’ll need to ask specific questions that help move the sale forward.

Using these 15 best sales questions to ask, in the sequence that I’ve shared, is sure to move your sale towards a close quickly.

Don’t worry about using every question to get started. Just pick one question from each category and introduce them into your sales process starting today!

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© Shawn Casemore 2022. All Rights Reserved.

The 15 Best Sales Questions to Ask (Ever!)

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