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ValueCore Team

9 Powerful Sales Questions to Ask Prospects – Open-Ended and Structured Versions

Published on August 17, 2022

Why Open-Ended Sales Questions Work

You should ask an open-ended sales question at the start of every discovery call. The first question should always be, “What would you like to learn most during this discussion?”

The power of this question is it allows you to understand quickly where the customer is in their buying journey. For example:

  • If the customer is early in their journey, they might simply be trying to educate themselves regarding what features or capabilities exist. They might say, “I’d simply like to understand what your platform can do.” You can follow up with a more specific question, such as “What is the main pain point you are trying to solve?”
  • If they are late in their journey, they might say, “I’ve evaluated a couple of vendors, and would like to understand how you are different, as well as your pricing model.

Based on how they answer this first most critical question, you may drive the discussion in different directions – either a product and differentiator deep dive, with pricing, or a problem statement overview and pain calculation.


After setting the stage with a powerful open-ended question, it’s important to advance into a blended open-ended/ structured approach to discovery. The benefit of asking structured questions are:

  • Make you look informed/ knowledgeable
  • Help you qualify/ disqualify the customer for Ideal Client Profile
  • Make optimal use of time
  • Makes synchronising/ tracking results in CRM more effective

9 Powerful Open Ended Sales Questions to ask your prospects – and their Structured Versions!

Topic Open-ended version Structured version*
Goals What are the top three things you’re trying to accomplish right now? Which of the following 5-10 items are you trying to accomplish in the current quarter or fiscal year (provide list, with checkboxes)
Obstacles How have you attempted to solve this issue in the past, and what was effective or ineffective? Are you using any of the following solutions today, and how would you rate their effectiveness? (Provide list, and rating system)
Size of Pain, or Cost of Existing Environment How would you quantify the pain or cost associated with your current approach? (Productivity cost) How many people on your team are affected by this problem, in a given month, and how many hours per month would you say they spend on this problem?
(Hard cost) Which tools and technologies are you using to address this problem today, and how much are you spending on each?
Purchase Process Can you walk me through your decision-making process? Who else would need to be involved in the decision-making process?
What specific criteria will be considered in your decision process? (include drop down list)
Source of lead How did you find us? Where did you find our product/ service / company? (include drop down list, including Google search, LinkedIn ad, reference, etc.)
Budget Amount What kind of budget do you have allocated for a solution like this? As you think about our solution/ service from a pricing perspective, what is the most appropriate comparison to what you are spending on today?
Budget Source Where would you anticipate getting budget for this type of purchase? In the past, we have been able to attach our solution to the following departments from a budgetary perspective. (Provide list, and use case/ ROI for each). Which of these would be feasible in this case?
KPIs/ Metrics How will you measure the success of this investment? Which of the following KPIs/ Metrics would you like to be able to track for improvement as a result of this investment? (Provide set of metrics with checkboxes)
Internal Selling Approach To get internal buy-in, how would you anticipate doing this, and how can we help? In the past, we have helped our buyers gain buy-in internally in the following ways: [Sample list to include: “Created a video, created a presentation with ROI embedded, shared examples of how other companies are using our solution, shared G2 reviews, shared video testimonials]. Which of these would be most helpful, if any?

When you should use structured questions

*Use the structured version in any of the following cases:

  1. You have limited time remaining in a call with the customer (e.g. call ending within 10 minutes)
  2. Trying to qualify / disqualify this customer as Ideal Client Profile
  3. Customer’s answer to open-ended question is light/ weak

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