How to Make Sure You’re Asking the Best Possible Sales Questions

Questions are the conversation starters that help sales professionals engage and convert buyers. Find out the right questions to ask and when to ask them.

February 16, 2017

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Asking the right questions at the right time is a quality that separates top sales pros from the rest. Doing so makes the salespeople look more credible in the eyes of a prospective buyer. Plus, it helps them gather insights that can be used to propose the best solution – one the prospect finds compelling. In other words, it puts them in a better position to win deals. This post outlines some of the key questions to ask in every B2B sales engagement.

Lead Them Down the Path

Sales pros can ask the right questions at the right time by mapping to the prospect’s stage of the buying cycle. But first, it’s important to know which stage your prospect is in. Sometimes you’ll get this info from your research. Other times your initial question can help you determine you’re prospect’s stage. For example, “How do you envision us helping your business?”

While each company’s definition of the stages may vary, the basic ones are:

  • Awareness. This is the time to ask questions that help determine buyers’ top-of-mind concerns. Understanding these will help you frame questions that plant the idea that your solution is worth consideration.
  • Consideration. At this stage, buyers are weighing their options, so it’s smart to ask questions that uncover the options being considered and get the buyer thinking about the value of your solution over others.
  • Decision. When prospects are ready to buy, it’s important to make sure they have the budget and authority to spend it, and understand when they plan to make the purchase.
  • Purchase. While the purchase phase is mainly about hammering out formalities and legalities, this is an opportune time to ask your new customer what metrics will help prove the value of your solution once it’s being used.
  • Repurchase. Encouraging existing customers to renew a contract or make an add-on purchase is one of the quickest ways to bring in revenue. Make sure you understand whether or not they realized the expected value from their first purchase. If so, that paves the way for a renewal. If not, asking how they are using the solution and why it is not meeting their needs may uncover opportunities for an up-sell or cross-sell.

The Basics

It’s a good idea to keep your questions open-ended. Doing so allows your prospect to do most of the talking while you do most of the listening. While much has changed about sales, thoughtful questions followed by intent listening is still the best way to gain a thorough understanding of the problem you’re trying to solve. It’s also a good idea to repeat back your understanding of the answer to confirm whether you’ve understood it correctly.

Uncover a Problem

You can’t possibly propose the most fitting solution if you don’t know why the prospect needs a solution in the first place. At the same time, your solution can only solve certain problems. The key is to find an intersection between the buyer’s needs and what you can offer. During your discussion, ask questions that relate to your solution but frame them around your prospect’s business. For example, if your company’s solution addresses product lifecycle management, ask questions such as “Can you describe your process for dealing with product quality issues?” Sometimes an assumptive approach can help get answers. For example, “What is the primary cause of your company’s time-to-market delays?”

Make a Change Worthwhile

Often the biggest barrier to closing a deal is getting the prospect to see the value of changing the status quo. Rather than try to convince buyers to embrace a new perspective by telling them other companies are doing it, put yourself in their shoes. Prospects needs to feel the pain – or understand the potential impact – as it relates to their everyday work environment and business. Get them to consider this by asking questions such as “Could your time-to-market delays lower your market value?” or “Could your product quality issues lead to customer churn problems?” You could even make it more personal with a question such as “Could the costs to rework problematic products impact your department’s budget or your ability to satisfy the CEO’s goals?”

Listen Before Responding

The questions you ask are meant to encourage an ongoing dialogue and make prospects feel you are focused on helping them. The last thing you want to do is come across as following a script! To hold up your end of the conversation, you need to listen carefully and respond thoughtfully. Oftentimes that takes the form of asking relevant follow-up questions.

Let’s say the buyer agrees that product quality issues could trigger customer churn. Your follow-up question might be, “What level of churn can your company tolerate before it’s in danger of missing this year’s revenue goals?” By truly listening, you can engage the buyer in a way that shows you grasp the strategic importance of their issue while bringing value to the conversation – and underscoring the urgency of making a purchase.


While top-notch sales professionals seem to enjoy unfair advantages, the reality is that every salesperson can elevate their game by better preparing for every buyer interaction. Knowing the questions to ask and when to ask them provides a solid foundation for the conversations that trigger buyers to take action and make a purchase. 

Now that you know the right questions to ask, download The Sales Prospecting Toolkit for everything you need to identify the key people in a target account.