Whatever you do, do not ask this sales question:

What does a typical day for you look like?

And you might read that question and think you would never ask that question anyway. What I want to talk about here is more the type of question, and here are three additional examples that could be more in the direction of what many salespeople might ask:

What keeps you up at night?
What is your biggest challenge?
How is everything going?

While those may sound like good questions to ask, this type of sales question is flawed for these reasons:

  • Too broad: These questions are too broad and can be applied to many different areas.
  • Difficult to answer: With these questions being so broad, they can actually be difficult to answer.
  • Unpredictable: It is also very difficult to predict what the prospect will answer with
  • Not productive: The prospect may answer with something that has nothing to do with what you sell.
  • Not efficient: You might waste valuable time talking about something that has nothing to do with what you sell.

I believe the key to being successful as a salesperson is asking questions, but it is important to ask questions optimized for the product or service you sell. Here is a step-by-step process for creating an optimum set of sales questions to ask. To demonstrate these steps, we will use the example of trying to sell the upgrade to a web-based version of accounting software to a customer who uses a desktop version.


Create a list of improvements

The first step in our process to create the best sales question to ask is to brainstorm the key improvements your product or service has to offer. Here are the improvements we have to offer when someone switches to our web-based accounting software.

  • Access from any device
  • Don’t worry about backing up and losing data
  • Easy to share with CPA
  • Don’t have to updates and bugs\


Create a list of pain points

The next step in the process to create the best sales question to ask is to brainstorm a list of pain points you can help to solve with your product or service. Below are pain points that are solved be the improvements we came up with.

  • Can only access from one computer
  • Potential to lose data
  • Difficult to share data with CPA and employees
  • Issues with bugs and version updates


Create a list of pain questions

Once you have a list of pain points, you can then create a question to ask for each pain point that helps you to probe to see if the prospect has that pain, challenge, or concern.

  • Have you ever needed to access data when not at main computer?
  • How concerned are you about losing data?
  • How often do you need to share data with employees or your CPA?
  • How often are you impacted by bugs or version updates?

These questions will be much more efficient and effective at finding out if the prospect needs what you sell.

We hope this helps you to have more clarity as to the best sales question to ask for your product or service!