Sales Coach Christine Harrington

7 Unanticipated Questions to Ask Prospects

The 21st-century salesperson (if worth one’s salt) knows sales is about asking questions and listening to what the buyer has to say. Hopefully, long gone is the 20th century pushy, snake oil salesman.

With that said, listening is key but it’s not the only key to build trust with the buyer. Here is an important way to begin building trust and it will differentiate yourself from the competitors…..Get out of your rut of asking the same questions during your sales appointments.

Here are seven unanticipated questions to ask a prospect

  1. Why do you think that? Refrain from asking questions that can be answered with a simple yes or no answer. The key is allowing the buyer to answer in a way that will give you as much information as needed to help the buyer. So be sure and ask open-ended questions like “WHY” or “Can you elaborate” or “Tell me more.” Asking unanticipated questions will stimulate the buyer to think deeper about the problems and issues you can solve.
  2. What would be your perfect solution? This question helps the buyer to explore the most important details of what they need. This will greatly help you to know how to customize your pitch around this answer. Plus it shows the buyer that you want to help them the best way you can.
  3.  Can I tell you about myself? This may be an unanticipated question for you! It’s important that the buyer hear your story because this builds trust and rapport. Learning more about you and your company helps the buyer understand who they’ll be working with. However, be sure to keep it brief and don’t drone on and on.
  4.  If you were your competitor, what one thing would you do? This question is a great one for B2B sales. It allows the prospect to think about their situation from different angles and viewpoints. The buyer may often come up with their own perfect solution which you can tailor your pitch around.
  5. Do you prefer I quit calling? When the call or appointment is not going well, there’s no reason why you shouldn’t be very direct with the buyer. Save yourself the time and hassle, especially if you’ve made a decision that it’s time to move on. This unanticipated question may take the buyer by surprise and you may get a more direct answer. They could express an interest or give you another smoke screen answer. At least you’ll know and can move on.
  6. What worries you the most about your problem? You can also state the question by including the problem. i.e. “What worries you the most about not staying up to date and current in digital marketing?”  This also works if you want to flush out what worries the buyer about moving forward. Often times other concerns may surface that you need to overcome. One word of caution, if things are moving along nicely, you may not want to ask this question. Why bring up more opportunities for objections!
  7. Have I asked you everything that you need me to know? This is a question for the end of the sales conversation. It allows the buyer to think deeper. And it shows that as a professional you’re concerned about the buyer and not just about landing a sale. Often times, the buyer will pause and think of one more thing to discuss. 

This week during your sales calls integrate some of these questions into your sales conversations. See if the buyer answers you in a deeper more detailed way. Then come back and share your stories in the comment section below. I’d love to hear your success stories.

Would you like more information about how to improve you or your team’s sales conversations?  Schedule a complimentary introductory call session with me by clicking here.


Christine Harrington is the Savvy Sales Lady, helping sales teams and individuals win more sales through a unique way of selling called Peak Performance Mindset. Christine brings 40 years of selling experience with Fortune 500 Companies, to help you shorten the learning curve, move past your selling blocks and position yourself as a Peak Performer. Sales Leaders, Sales Managers, Sales Teams, Small Business owners and their employees have captured their edge by attending Christine’s Peak Performance Mindset Workshop and Coaching. Learn how she can help you or your team. Get the edge by clicking here

Leave a Reply