7 Questions to Build Connection with Prospects

A friend of mine used to say, “There are two types of salespeople, 1) those who make lots of money but are smarmy and gross, and 2) those who are super nice, give tons of free information, and leave broke.”

It doesn’t have to be that way.

So how do you make your customer feel comfortable, give massive value, and close the sale at the same time – minus the smarmy-factor?

They key is connection. And connection is built through asking high quality questions – and then listening.

These 7 powerful questions will help you to engage your prospect while building trust and rapport. Weave these questions throughout your sales process to uncover wants and needs and position you to provide a solution, while staying a mile away from smarmyville.


“Sure, I can help you with that. Is it ok if I ask you a couple questions so I can give you the most accurate information?”

Frequently the topic of price may be the first question that comes up. It may be because customers just don’t know what questions to ask, and cost is a logical starting point.

By asking this question you are requesting permission to explore your customer’s needs and priorities beyond the price. At the same time, you are also taking control of the conversation. Now you can begin to better understand your prospect’s concerns and expectations.


“Tell me more about that?”

Don’t underestimate the power of this simple, open-ended question. This question may seem superfluous, but in fact it is an insightful way to pull out additional details that they otherwise wouldn’t have shared.

Not only does it help to keep your conversation flowing (especially if you’re at a loss for what question to ask next), but it also allows your customer to better elaborate on any frustrations, fears, or concerns they may have in making this buying decision. By encouraging your prospect to have the floor, you are equipping yourself with the information needed to best serve them.


“So how do you want ___ to be different by [time frame]?”

The first blank is for the main benefit you offer and the second is the reasonable timeline to expect the results. For example, if you are selling marketing services, you could ask, “How do you want your online presence to be different by this time next year?”

This question shows real curiosity about the customer’s needs. Additionally, and perhaps more importantly, you are allowing your prospect an opportunity to share their goals and expectations.


“Suppose we were having this conversation x months from now, looking back, what would have to have happened for you to feel really happy with ___?”

Similar to the previous question, this query dives further into expectations. Now you know on what basis they will be judging your company’s performance, and exactly what you need to deliver to create a raving fan.


“If you don’t mind me asking, what factors other than price are important for you to consider when making this decision?”

If the objection of price is still coming up in your conversation, this is a fantastic question to ask. It acknowledges that price is a consideration, but also that it is not the only (or even the most important) consideration. Putting the subject of cost aside for a moment helps the customer to get clear on how they define value. If you can deliver on that value, price will take a back seat every time. (Don’t believe me? Consider price shopping for a surgeon.)


“How does that fit with what you had in mind?”

If you are nearing the end of your sales process and preparing to ask for the sale, this is a perfect question to ask. Without any pressure, you are checking your prospect’s temperature to find out if the solutions you presented are aligning with their needs. Assuming you have already built trust, if there are any remaining concerns that you have not addressed, it will come out here.

Hint: if you’re getting, “I have to think about it” when you ask for the sale, that is a sign that you’ve missed something and need to incorporate this question. It is far easier to overcome objections before you ask for the sale than it is to get out of the “think-about-it-zone” when the decision question is already lingering.


“So what do you think we should do from here?”

This is the softest closing question in the history of questions.

It puts the ball in your customer’s court. What do they want to happen next? Likewise, it gives you one more chance to satisfy any remaining concerns, or propose a revised solution. This close is not salesy or pushy. It is collaborative.

The Final Question

If these steps are followed, and you have fully understood your client needs, you are likely to hear your prospect say, “When can we get started?” as a response to your last question.

When they answer your question with a question, you’ll know you’ve done your job in building a great connection, and are on track to a long-term relationship of repeat business and referrals.