9 Powerful Sales Questions to Ask

Struggling to close your warm leads? Not confident that you’re truly understanding your prospect’s needs and your discovery calls? Then you’re going to want to stick with me until the end of this article, because I’m going to go over nine powerful sales questions that you can ask to close more deals, increase your average deal sizes and crush your quota. I’m going to go over each question as well as why we ask these questions and what makes them so powerful.

For over five years, I led the sales, marketing, and customer success teams of a VC-backed startup going from zero in revenue to over mid seven figures in revenue. From humble beginnings of selling out of a fax room to actually having multiple years of bringing in over a million in quota. I’ve seen my share of what it takes to close deals, as well as coach account executives to be successful on the job. My sales style is direct professional and driven by consultative selling.

So if you’re excited to learn about these nine powerful sales questions be sure to check out my YouTube channel to get notified every single week of new videos that help take you from zero to self-starter, as you get more customers, win more business and scale your business without further ado, let’s get started.

Question 1: What led you to reach out to us?

The first powerful sales question we can ask is, “What led you to reach out to us today?” And the reason why we should ask this question is because it allows us to come from a productive place in a sales conversation that’s more collaborative as opposed to salesman-driven. People hate being sold to. And so when we ask this question of what led you to reach out to us today, it really helps us level with our prospect and try to see why specifically they need our potential solution.

Question 2: Tell me about how you’ve attempted to solve XYZ in the past.

The second question that we should ask our prospect is, “Tell me about how you’ve tried to solve X, Y, Z problem in the past?” The reason why this question is so powerful is because it allows us to continue empathizing and understanding our prospect. For example, you wouldn’t know that our prospect might be approaching their solution entirely wrong, unless we asked this question and understood how they were grasping their problem. So by asking this question, we are continuing to learn more and uncover the layers of the onion behind our prospect and why they’re reaching out to us.

Question 3: Tell me about what went well and what didn’t went well when you previously worked with XYZ.

The third question to ask when it comes to powerful sales questions is, “Tell me about what went well and what didn’t go well the last time that you worked with XYZ vendor on solving XYZ problem?” And the reason why we asked this question is because it helps us identify with this particular prospect, what they value most out of a potential service or product provider.

By taking the time to understand our prospect here, we better position ourselves as trusted advisors in this discovery process as to whether this prospect and our service or product is a good fit together. It’s also helpful in a buyer’s journey because it allows us to actually listen first to what the prospect needs, as opposed to just pitching our product from the very beginning.

Question 4: What does not achieving XYZ desired goal mean to you?

The fourth powerful sales question to ask is, “What does not achieving X, Y Z goal mean to you?” And the reason why we ask our prospect this question is because it allows us to attach stakes to our sales conversation. In other words, by helping our prospect understand what the consequences of them not solving their problems or challenges are it allows us to really accelerate the urgency of our actual sales conversation.

For example, if I were pitching consultative services to a VP of Sales, to help them improve their sales process, I might ask what the stakes would be if they were to face a situation in which half of their team did not hit their quota for more than half a year. That VP of sales might tell me that if that were the situation, what might happen is the CEO would lose faith in him, as well as the board.

And as a result, he might have significantly less freedom as to how he runs his team or even worse, he might lose his job. So by attaching these stakes to this particular conversation in our discovery process of better understanding the need that arises with this particular person, we can actually move the sales conversation along with a greater sense of urgency.

Question 5: How urgently do you need to solve XYZ problem?

The fifth question, “When it comes to powerful sales questions is to ask your prospect, how urgently do you need to solve XYZ problem?” The reason why we need to ask this question is because it helps us prioritize our pipeline. If we know that our prospect, for example, needs to make a decision in the next two weeks, it means that we’re likely to have follow on conversations and even a closing call within those next two weeks. However, if this is a problem that our prospect isn’t actively trying to solve, then it might just be put on the back burner for a few weeks or even several months before the prospect is ready to be moved into a closing conversation.

So knowing where the buyer is in the buyer’s journey of awareness, consideration, and decision is crucial when you’re trying to prioritize your pipeline and make the most of your finite number of meetings that you can take every single day. That’s five of nine powerful sales questions.

Question 6: Tell me about the approval process for a purchase like ours.

Let’s move on to question number six, these sixth questions to ask your prospect when it comes to powerful sales questions is, “Tell me about the approval process for a purchase like ours.” The reason why we want to ask this question is because it allows us to identify all of the potential relevant stakeholders in the closing conversation, but ahead of the closing conversation. And what I mean by that is let’s say, for example, you’re talking to a prospect that’s lower in the overall food chain of decision making.

Well, if that were the case and you weren’t to identify the decision maker upfront, then that could lead to potential lag time in your deal, actually closing because they have to go to their supervisor and get buy in from that supervisor before getting the final sign off. So by asking your prospect about what the typical buying decision is like you are helping them connect the dots within their own department or their own company to help bring your product or service and solution to their company.

By asking this question, we’re setting up a great win, win situation for not only your prospect, but everybody else that your prospect reports to because in that situation, everyone is going to be able to have the opportunity to get buy in and to feel confident about the decision to buy your company’s product or service.

Question 7: Before we finalize things, is there anything you would like to go over again or are unsure about?

The seventh powerful sales question is to ask your prospect, “Before we go into next steps, is there anything that you’re unsure about or would like to go over again?” Another way to ask this is, “Before we finalize things, is there anything else that might hold us back from moving into next steps?” The reason why we asked this question is because it allows us to give the prospect an opportunity to speak about any potential concerns or objections that they may have to the actual sale occurring before the actual closing process is happening.

I like to be closing conversations as purely logistical conversations. And what that means is that by the time we’re having a closing conversation, we’ve already gone through all the potential reasons as to why you wouldn’t buy my product. And you’re only focused on specifically what the next steps need to be in order to make a deal actually happen. And so by asking this question, before you go into your next steps of invoicing or whatever your process may be, it allows us to slow down with the prospect and really again, build your confidence with your prospect, that both of you have addressed every single stone in the decision making process to choose your company as the solution.

It is way more productive to handle objections when it is not in a high stakes conversation than it is to do so at the very last minute, literally right before you are about to send an invoice their way, handle all your objections in your lead up conversations to your closing conversations so that your closing conversations can be purely logistical.

Question 8: If you were to work with us, how would you measure success within 3, 6 or 12 months?

The eighth powerful sales question to ask is, “If you were to work with us, what would you expect from us within the next three, six or 12 months?” You can change the length of time, however you’d like. But the reason why this question is so powerful is because it actually allows us to begin to understand what this prospect values most from a product or service like ours. Furthermore, it actually allows us to set up our customer success teams for success.

How many times have you actually bought something in which the sales person is doing the legwork of the introduction for the customer success team? It’s not very often. And so by asking this question, we’re actually setting up our customer success team for great success, because what we’re going to be able to do is in our closing conversation, we can actually tell our prospect, “Hey, by the way, I’ve already told our customer success team, and who’s going to be your customer service rep that you are looking achieve X, Y, Z goal within the next three months of working together. And so when you get onboarded, we’re going to begin the conversation from there.”

Imagine the world of a difference that your next client is going to feel when you have actually set them up for success from day one. Having this is a great way to up your level of professionalism as a sales professional, and really set not only in yourself and your deals up for great retention in the long-term, but also to set up your teammates and your company for success.

One more powerful aspect about asking this question is that if you do so in a very smooth way, it can actually be used as a forward projecting closing technique in a very subtle closing technique. As you’re already talking to your prospect as if they are going to be a customer of yours.

In other words, it’s a presumptive close. It assumes that this prospect that you’re talking to is already a good fit for your particular product or service. And then you are ready today to introduce them to the customer success team member that’s going to be the hero for their particular problem.

Now let’s head into the last and final question when it comes to powerful sales questions.

Question 9: I’ve really enjoyed working with you to solve XYZ. Before I hand you off to our customer success team, I was wondering if you can think of one other person who could benefit from learning more about our product or service?

My ninth, most powerful sales question, and personally, one of my favorites to ask the prospect at the end of those closing conversation goes something along the lines of, “I’ve really enjoyed working with you, Mr. or Mrs. Prospect. I was wondering before I pass you off to our customer success team, can you think of one other person or company that could potentially benefit from learning more or hearing about our product or service?”

If they respond in the affirmative, which from my personal experiences, 8 times out of 10, they will, you will say something along the lines of, “Would you be so kind as to introduce me to X, Y, Z person or company, I’ll do the heavy lifting and I can give you a template that you can use to make the introduction. How does that sound?” The reason why we ask this question is obvious. It’s one of the lowest lift ways for you to continue building your pipeline and replenishing your pipeline.

As you’re about to close a deal, there is no better person to help you think about who your next deal is going to be, then the deal that is about to just close with you. And so by building this habit into your sales techniques of asking for referrals and building referrals into your overall sales conversations, you are giving yourself more opportunities to close new business. It won’t always work, but by simply asking this question regularly in your sales conversations, you’ll notice that you do it in other aspects of your sales techniques as well, in not only your phone calls and your discovery calls or closing calls, but also in your emails. And so by building this habit up, it is one of the easiest ways for you to crush your quota.

Either way, the bottom line is that by asking this question, you are building your own positive habits of making the ask for a referral and continuing to replenish your pipeline as you close one deal and move on to the next, make sure you ask this question, cause it is so easy and people love to make introductions and be helpful to other people.

Big takeaways

There are two big takeaways that I want you to remember.

  1. The first one is to always ask your prospects open ended questions. It allows your sales conversations to become way more collaborative and way less salesy in general, which allows you to build more rapport with your prospects, whether or not it works out with that particular prospect.
  2. The second thing to remember is that good salespeople always guide their prospects. They help their prospects understand what problems they have and why those problems are important or not important to their particular business. And the other thing that they do is they always help explain how or why their particular product or service can solve the problems that this business owner is facing.

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