Best Questions To Ask In Sales

The most important skill to have in sales is listening. Unfortunately, not a lot of salespeople are taught this right off the bat in their sales careers. But for those who do eventually learn this lesson, what follows is a desire to understand what questions to ask and when. After all, the best way to listen is to encourage the other person to talk more, and an easy way to do that is through asking questions.

I think some questions are asked just for the sake of asking. We’ve all been on the receiving end of a cold call where someone is reading off a script, or worse yet, a full-fledged demo where it seems like the sales rep is going through a playbook on how to run the meeting. With that in mind – and because I value authenticity so much – I do not tell my sales reps what they need to ask. I just give guidance on what kind of information will help them to best understand the needs of their clients. And from there, I provide the types of questions that will help them become better listeners.

With this in mind, let’s look at some questions that you can reliably ask in most settings to gain a clearer understanding of your client’s pain and needs.

Why did you ask that?

Of course I am starting with a question you can ask when someone asks you a question. What I have found with most questions your prospect asks is that they are usually grounded in something entirely different than the premise of the question itself. For example, if they ask you how long you have been in business, they are almost certainly not actually interested in the literal answer. What they are probably interested in finding out is whether or not you have a track record of success. The distinction is important. A company can be around for a while without a positive track record of success. Meanwhile, a company can be relatively new with a very well-established onboarding guideline and mutual action plan that would make that client immensely comfortable. The only way you can possibly get to the root of the question and what they are really asking is by asking them to clarify the real intent of the question.

In my Objection Handling workshops, I lay out four steps to overcoming concerns. The third step is “Narrowing,” which is where we narrow the scope of the objection. For example, if someone says “I am worried about change management,” that is a very broad objection and therefore quite difficult to overcome. However, if they clarify that objection to state that they are a team of one and that they are concerned that buying the solution would result in them being overwhelmed, this is a much more specific concern, which by default makes it easier to work through.

As a general practice, we should always be trying to narrow the scope of questions and concerns. I do not suggest doing this as some sort of scummy trick. I suggest doing it because most objections are actually much narrower than the prospect says. Sometimes the prospect knows this, but more often than not, they actually do not understand how specific their objection is. They typically have some sort of emotional response and blurt out a broad objection. It is only by forcing them to work through what actually scares them that you can narrow it down to where the real fear lies.

In practice, I suggest techniques like labeling, mislabeling, and mirroring as ways to encourage a prospect to speak more and narrow the objection. Those are covered in another blog. In the scenario where you are asked a question, the easiest and most logical way to respond is to understand the motivation of the question. So just ask them why they asked the question.

Why Haven’t You Done That Yet?

I wrote a blog not long ago about the importance of this question, and I decided I am going to write an entire book about it. For me, this question unlocks where someone falls on a pyramid from the bottom (pain) to the top (fear). Along the way there are various layers, like urgency, top urgency, and prioritization of pain (among others). The long story short is that there is a journey people are on when deciding whether or not to solve a problem, and this is the question you need to ask to figure out where they are on that journey.

I think we live in a post-pain sales world. What I mean by that is that in a lot of cases – perhaps even the majority – your client has the pain that you can solve. So in that sense, having the pain has become commoditized. Think about it – every day you make thousands of decisions. Putting one foot in front of the other. Then the other foot. Maybe you decide when to eat. When to respond to an email. In any given moment of time, you are making the decision to do the thing that you think you most urgently need to do. Amidst that, you are ignoring the thousands of other problems you will eventually solve. Through this lens, we live in a post-pain sales era. Instead, we live in an era where prioritization and urgency are vastly important. And it is some equation of the size of the pain multiplied by the level of urgency that helps people come to conclusions about solving something right now.

With that being the case, “Why haven’t you done that yet” is the perfect way to understand why a specific pain has not risen to the level of being solved yet. It actually very well may be the case that the answer is something like “It was not the most urgent pain, but now it is.” This is obviously the answer salespeople want to hear. But you still need to know why it was not solved before if you want to help that person solve it now. There may be roadblocks that existed previously that we still need to be aware of today.

Why Would You Do This? & Why Wouldn’t You Do This?

I like asking these questions as a tandem because it helps me to understand the full thought process of a prospective client. What do they see as the upside scenarios and the real motivators for acting? What do they see as the primary risk drivers of taking action? I actually think most buyers do not ask this question to themselves. As sellers, it is important for us to drive their awareness. It very well may be the case that they should not buy our solution. The only way for them to figure that out is if they think through the pros and cons. Also, we as sellers should have a say in the dialogue to help understand two things:

1. Can we deliver the positive outcome they speak about when they say why they would do it? Best to be honest if we cannot and re-set expectations.
2. Is the negative outcome they are worried about realistic or driven out of fear? If the latter, how can we help them understand it better?

We need to be fair to our customers and the best way to do that is to help them to be fair to themselves. Encourage them to think about the upside and downside, and then let’s talk about how realistic their answers are and whether or not moving forward is worth it.
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Let’s say you moved forward and a year from now you were talking about how it went with your leadership team. What would you want to be able to say that happened over the last year?

This one is admittedly a much more complicated question than the other ones I asked, and that’s OK. This one utilizes the concept of “Visualization.” Most performance coaches in athletics encourage their athletes to deploy this technique to help them feel more in tune with what success might feel like. If we can imagine it, we can do it.

While on one hand I like this question because it effectively utilizes Visualization, I really just like it because I want to know what my prospect wants to be able to say to their boss in a year if they successfully use our product. It’s really a more long-winded way of asking the last question, “Why would you do this?” But there is a subtle difference. What you want to be able to say to someone is a little bit different than the underlying reason why you want to do something. The two are obviously related, but you what you want to say normally reflects on what you have to gain (personally) by doing something. So this is really a much more subtle way of asking a more direct question: “What are your personal stakes in doing this?” If you prefer to take the more indirect approach, ask it this way instead.

How does that make you feel?

If you were to go and run a straw poll of anyone on my sales team – or anyone who has ever reported to me – and you asked them what my favorite question is, this would be it. And it wouldn’t even be close. Why is that?

Well, first and foremost, I love open-ended questions. Any time I see someone ask “Does that make sense?”, I cringe. That is a ‘yes’ or ‘no’ question. I would much rather ask how the person feels. If it doesn’t make sense to them, I am sure they will let me know. In fact, by asking how they feel, I am inviting them to let me know if it does not make sense – and in a much less confrontational way.

Open-ended questions are wonderful because they force the prospect to talk. As salespeople, it is our job to listen. We can only do that if the other person is talking. As I mentioned before, the prospect talking is – by default – forcing them to narrow in on what they like or do not like. Their objections become clearer and more well-defined. This is helpful to move the dialogue forward.

But the real reason why I love asking how someone feels is because we are all emotional buyers. At the end of the day, we need to know how the other person is feeling. They may very clearly understand that there is a preponderance of evidence to suggest one thing and yet they may feel something else entirely. We need to make them feel comfortable telling us that they feel differently than how they ought to feel based on all of the information that has been provided.

The same is true in reverse. When you ask someone how they feel, they may often be very emphatic. We need to understand what gets them excited. After all, “Why would you do this?” was one of the earlier questions we should seek to ask. “How does that make you feel?” is one of the simplest and most effective ways to understand the emotional state of your buyer.