It is critical to ask sales questions when you are out there selling. But the difference between being a good salesperson and one that is consistently overachieving is asking the RIGHT questions.

Let’s take a look at one of the common sales prospecting questions that many salespeople think is good and we will show you why this is actually one of the worst to ask.

The Sales Question We Are Referring to Is….

What keeps you up at night?

This can often be seen as a very sophisticated sales question and it will uncover information that will be very valuable. We will explain why this is not the case.

What is Good About the Sales Question
But first, let’s look at what is good about this probing question. First, this question is definitely a step in the right direction as many salespeople don’t ask any or enough sales questions.

This can be the case because many salespeople get hung up on talking primarily about their products and company as they attempt to build interest. And they often skip over focusing on the prospect and identifying if there is a need for the products or services that they sell.

This sales question does accomplish two very powerful things. First, it gets the conversation more focused on the prospect. And the second thing that it does is it looks for pain that the sales prospect is having or is concerned about.

What is Not Great About Sales Questions Like This
What is not great about this sales question is that is too broad. And that means the answer that the prospect can come back with can be in any number of different areas.

If you ask that question to a business owner or executive, they could come back with an answer that pertains to HR, Operations, Finance, or IT. The problem with that is that you likely sell a set of products or services that impact a very specific area and their answer might not come back matching up with your area of specialization and expertise.

For example, let’s say that you help to improve operations for a business. And the prospect answers that their HR and staffing keep them up at night. This is a not-so-optimum situation and it is caused by asking a probing question that is very broad.

The Impact of this Mismatch
You accomplished something good when the prospect answers your probing question – you found out that they have pain. But it does not match with what you were looking for.

This creates a less-than-optimum situation because you most likely do not have deep knowledge in the area that is mentioned if there is a mismatch, or at least not as much knowledge as you do in your area of expertise.

This means that you will be less likely to know what best to say next or won’t have as much control over the conversation as you would if you were talking about the area that you can help with. And if you continue to talk to them about the area that they responded with, you are wasting valuable time talking about something that you have no ability to help or impact.

Make this Small Change
If you agree with any of that, you can make one small change to completely eliminate all of these concerns and get to the key thing that you are looking for. Just simply make the question less broad and be more specific about the pain you are looking for.

Here are some examples of sales questions that look for pain in a particular area:

How concerned are you about the amount of time it takes to onboard new sales hires?
How important is it for you to decrease sales staff turnover?
How confident are you that your sales resources are asking the right questions?


SalesScripter will help you to develop the key sales questions that you need to ask when prospecting.