Advanced Sales Techniques: The Skill of Asking Questions

advanced sales question skills video


To be successful at sales, you need to do more than just sell a product or service – you need to build relationships, understand customer needs, and close deals.

Our previous article identified six advanced selling skills critical for sales success and focused on the primary “active listening” skill.

Now we turn to another vital skill in the customer-focused sales process: the ability to ask questions.

Why Questioning Skills are Important

Asking questions is a crucial sales skill. You can gather information about your prospect’s needs and pain points by asking the right questions. You can then use this knowledge to tailor your sales pitch and close the deal.

Here are some tips to get the other party engaged in talking even before you begin to ask questions:

  • Smile, nod, and use short phrases like “I see,” “that’s interesting,” and “I understand.”
  • Use comments like “I’d like to hear more about that.”
  • Help the person clarify their thinking by restating and paraphrasing key information as it is given, e.g., “What you’re saying is …”
  • Summarize to encourage extra information, e.g., “To recap on the current situation …”

When to Use Questions in the Sales Process

Asking too many questions can be off-putting. You don’t want to come across as pushy or interrogative. And you always want to let your prospect do most of the talking while you listen.

However, you need your questioning skills when:

  • Initiating a discussion,
  • Exploring customer needs,
  • You are putting your toe in the water to see if the customer is hot or cold towards making a purchase.

We previously identified “active listening” as a necessary skill in customer-focused selling. Asking the right questions is critical to this process, which means you need preparation time to consider the most effective style of questions for the situation.

The Art of Asking Questions

There are two types of questions to use.

  1. Closed questions can be answered with a simple yes or no. They are often used to confirm information or to gather basic data points. An example might be, “Have you used our product before?” Closed questions are important because they help to establish a foundation of information. However, they should not be overused because they can appear pushy or intrusive.
  2. Open questions invite elaboration and cannot be answered with a simple yes or no. They are often used to encourage dialogue and to get the prospect talking. You can extend this with “deep dive” questions that get them thinking to explore their issues in depth.

It is essential to ask questions and clarify your understanding of your customer’s statements, as well as to collect extra information from them so you can expand on the conversation. Strike a balance by asking a mix of open-ended and closed questions.

Here are some examples of good probing questions to ask in a sales conversation:

  • What challenges are you facing with (product/service)?
  • How do you currently handle (problem)?
  • What would be the ideal solution for you?
  • What other options have you considered?
  • What budget do you have for this project?

To make your questioning effective, you will want to avoid an approach that could be interpreted as an interrogation. At the same time, you should massage the questioning delivery, so you do not sound like a robot.

Usually, in the conversation, you try to get to the bottom of the customer’s pain points so you can help them achieve their expectations.

You must be sensitive during this process and ask questions designed to fit their specific situation.

Start with questions that allow the customer to feel comfortable before moving on to the more focused, deep-dive questions designed to reveal more important information.

You can ask the same question differently for a different response. For example:

  • A closed question could be: “Have you tried any solutions?”
  • An easier open question could be: “When did you notice this problem?”
  • Finally, a deep-dive question could be, “What makes you think ‘X’ has been such a big problem for you?”

When you want to close the sale and need a clear answer, closed questions are helpful, e.g., “are you ready to go ahead?” or “If that answers all of your questions, shall we agree on a price?”


Excellent questioning skills are a crucial component of selling as it helps you to better understand your customer’s needs and desires. The information you glean can help you tailor your sales pitch to their specific wants and needs. Additionally, your questions can show the customer that you are interested in them as an individual and not just trying to make a sale. Finally, questions are useful in helping to build rapport and trust between you and the customer.

Developing your ability to question and listen, will hone your selling skills and help you take your business to the next level.

Other articles in this series:

How to Improve Your Sales Skills as a Small Business Owner
The Power of Relationship Selling
Advanced Selling Skills: Customer Focused Sales
Educate and Collaborate

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