Have you ever mapped out exactly what questions you intend to ask your prospect…only to realize later that you should be asking questions that dig much deeper?
In reality, the best sales questions that truly determine your clients’ needs aren’t just those rehearsed questions you’ve lined up ahead of time.
Some of the most powerful sales questions are actually little, quick questions that happen spontaneously as the sales interaction unfolds.
These short, organic sales questions are key to digging deeper to create true value in the sales process.
In fact, quick sales questions can often make all the difference to the sale, taking prospects from vague to clear—building real, undeniable value.
Quick Sales Questions to Ask #1: “Unpack that for me.”
This is one of my favorite “questions”—and yes, I realize that it’s not technically a question. However, this inquisitive statement is a powerful way to get prospects to delve more deeply into something they’ve mentioned.
Let me give you an example. At the time of writing this, we’re all living through a time of great uncertainty in the marketplace. So, you might encounter a prospect who says something vague such as, “Yeah, right now things are just totally insane.”
Now, most salespeople will respond to that statement with something like, “Oh, I know exactly what you mean!” And then they’ll launch into an ineffective monologue trying to relate to the prospect about how crazy things are right now.
Instead, you should respond to statements like this with, “Unpack that for me.” A true sales professional wants to learn more. Why did the prospect say things are “totally insane” right now? Is it because of external factors? Or is something going on internally that you’re not aware of? Are things crazy for the prospect right now because of something that you don’t even understand?
The answers to these questions are crucial. Every great salesperson knows to ask quick sales questions to dig deeper at moments like these.
By saying, “Unpack that for me,” you’re inviting the prospect to explain what they actually mean by “things are just totally insane,” giving you stronger insight into their world—and their biggest challenges.
Average and low-performing salespeople tend to get uncomfortable when digging into prospects’ statements in this way. They just assume they know what the prospect meant, and they go with their assumption. This is a surefire way to have a surface-level conversation that ends up going nowhere.
But great salespeople know that asking quick sales questions can uncover often-surprising intentions and explanations behind the things prospects say. And those insights can make all the difference when it comes to building real value in the sale.
Don’t miss these opportunities to further the conversation with your prospect. Chances are, by simply saying, “Unpack that for me,” you will reveal a truly valuable piece of insight that will lead you to a much deeper part of the conversation.
It’s imperative that you understand your prospect better than any of your competitors do. Quick sales questions like “Unpack that for me” allow you to set yourself apart and gain deeper access to what’s really going on in the prospect’s world.
You should be using this phrase all the time when you’re talking to prospects. Remember that literally anything a prospect says can be “unpacked,” and could potentially lead you to a far deeper part of the sales conversation.
Quick Sales Questions to Ask #2: “What is that costing you?”
This is a high-level sales question. Most salespeople balk at asking this question, thinking it’s way too difficult or confrontational to ask prospects directly about cost.
If you’re one of those salespeople who would never ask a prospect, “What is that costing you?” then I have some bad news for you. You should stop reading this right now and just move on. Because this sales question is only for salespeople who either: A) have guts, or B) really see themselves as true sales professionals.
While pretty much every salesperson today talks to their prospects about some of the challenges they’re facing, only true sales professionals are willing to dig deep and take that conversation around challenges to the next level of insight.
So, don’t just be content to talk a little bit about your prospects’ challenges. Instead, constantly think about how deeply you can take that conversation to learn as much as you possibly can.
This is where the sales question, “What is that costing you?” comes into play. Once a prospect has explained a challenge (ideally, a challenge that you solve in your area of expertise), you must dig deeper to understand how much that challenge is actually costing the prospect.
Remember, the value of your offering in the eyes of your prospect is simply the difference between where they are today and where they want to be. Typically, where they are today and where they want to be is separated by some specific challenge they have to break through in order to get there. What you want to understand is, what is the real value of solving that challenge? What is that challenge actually costing the prospect right now, unsolved?
By asking, “What is that costing you?” you’re cutting straight to the chase, while helping the prospect think through the math of the actual value of solving that challenge. There’s not much that’s more powerful than that in a sales conversation. This is a prime example of how short, quick sales questions can transform a sale.
Quick Sales Questions to Ask #3: “Why is that?”
“Why is that?” is one of my all-time favorite sales questions. Or, if you really want to be a sales ninja, you can also just ask, “Why?”
This simple question is so powerful because it allows you to keep peeling back the layers of the onion in any sales conversation, at any time.
Great salespeople are like detectives. Do you remember the old Columbo TV show? If not, look it up on YouTube real quick. What you’ll see is a detective who’s constantly acting like he’s a little bit dumb, or like he doesn’t fully understand stuff…but really, he’s the smartest person in the room. This is exactly what we want to do in sales.
You should constantly be asking “Why is that?” and never assuming that you understand what the prospect means. Make sure you fully understand what they actually mean—and get the prospect to articulate what they mean on their own.
Many times, prospects haven’t really thought through the challenges they mention to you. By asking them, “Why is that?” or “Why?” throughout the conversation, you can help them think everything through, without any assumptions getting in the way. Force them to use their brain power.
I can’t tell you how many times I’ve heard prospects say, “You know what? I don’t know why. I haven’t really thought about that. But now that you ask, here’s what I think…” This is pure gold in a sales conversation, and it all comes about through the use of quick sales questions such as “Why is that?”
Your ability to take a prospect deeper and deeper into the sales conversation makes all the difference between closing just some sales and closing many, many more sales. And by the way, you’ll be doing it at higher prices, because now you’ve established yourself as a real expert.
The next time a prospect says something you don’t fully understand—or really, the next time a prospect says anything at all that seems important or interesting—ask, “Why is that?” Keep digging. Try to understand exactly what’s going on.
So, there you have it. Now you know 3 quick sales questions to ask to determine your clients’ needs. Which of these sales questions did you find most useful? Be sure to share your thoughts in the comments section to join the conversation.