8 Winning Questions Your Sales Reps Should Be Asking Every Prospect

8 questions sales reps should be asking

It’s not enough for your salespeople to be product experts, they also need to be capable of having the kind of conversations that position them as business experts and even strategic resources.

In order to do that, they should be asking the right questions. They can then use the answers they get to guide and advise their prospects towards making the most appropriate business decisions.

Coach your sales team to master these 8 questions.

1. “How long have you been faced with this challenge, and what has it cost you?"

Asking this allows the prospect to assign a number to the dollars being lost/wasted and helps reinforce just how valuable the right solution will be to them. Reps can then drill down on the question for deeper detail.

2. “What have you tried in the past, and how has that worked out?”

When a salesperson asks this question, they can determine where the prospect is on the buyer’s journey, and identify any competitors they may have experience with. If your team is trained with a flexible sales process, they’ll be able to quickly meet the buyer where he or she is on the buyer’s journey.

3. “How is this decision affecting you personally, how does this make you feel?”

There’s a lot of emotion involved in a buyer’s decision making process. While many salespeople try to determine a buyer’s needs, they often neglect to determine a buyer’s wants. Wants influence why a prospect will buy, and are typically based more on emotion.

4. “What would happen if you took no action and just left things as they are today?”

Asking this helps reps to determine if the prospect is qualified. It also allows the buyer to say out loud, in their own words, why moving forward without a solution simply isn’t an option.

5. “Who within the company, besides yourself, is accountable for this goal?”

This is another good work-around question to tactfully determine if the prospect is qualified to make a purchase. It also gives the salesperson a way to find out if all the necessary decision-makers are at the table.

6. “Where do you see your business or department in the next 6 months? In the next 3 years?”

Salespeople need to be focused on solving the immediate problem for their prospect, but they also need to provide a solution that fits with the organization’s future strategy and goals. A drill down question about why moving in a particular direction is important to the prospect can help to uncover additional emotional drivers.

7. “What, if anything, are you looking for in a business partner that you haven’t found?”

Asking this allows sales reps to address where competitors may have fallen short. They can use this information to differentiate themselves on their ability to deliver.

8. “As you move forward in your decision making process, what do I need to do to help you?”

This phrasing helps to lessen the intimidation or resistance a prospect might otherwise feel if asked directly about the decision making process. When reps ask this question, they allow customers to buy in the way they want to buy.


Your salespeople must first discover what a prospect perceives as value in order to become a valuable resource in their eyes. These questions open up a conversation that gets the buyer and seller sitting on the same side of the table, trying to figure out what’s best for the buyer.

It’s also crucial for your team to have a defined sales process in place. A customer-focused sales process such as IMPACT Selling® aligns with a prospect’s decision making process, and gives sellers the necessary steps to reach strategic advisor status.

Join us at our next IMPACT Selling Seminar to see the system for yourself and whether it’s right for your team.



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Lisa Rose

Lisa Rose is a Group Vice President of Sales at The Brooks Group. Lisa has passion for helping managers develop a unique, motivational sales culture in their organizations. She can drive sales managers who merely put out fires day to day to flourish as visionaries who can motivate their team and generate results for their sales organizations.

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