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Asking More Effective Sales Questions: 10 Tips

Sales is often a game of questions. Unless you ask the right questions, you won’t uncover the right needs. Unless you ask the right questions, you won’t understand the right problems to solve.

But there’s an art to asking these questions. Which is why I’d like to share the following ten tips for asking more effective sales questions.

1. Ask permission.
In some situations, it’s understood that you’re there to gather information. In other situations, it’s appropriate to show respect by asking permission to ask questions.

Example question:“May I ask you some questions about your business?”

This may be a rhetorical question, but it’s worth asking anyway.

2. Start broad, and then get specific.
Broad, open-ended questions are a good way to start gathering information. They put your prospect at ease because they allow any type of response.

Example question:“Could you tell me about your business?”

This is a non-threatening way to begin. Listen to what your prospect says and what she omits. Both will suggest areas to explore in greater depth, such as, “Could you tell me more about how absenteeism impacts your bottom line?”

3. Build on previous responses.
Any good interviewer knows that the most logical source of questions comes from the interviewee’s responses. Dovetail your questions with the responses by listening for key words.

Example question roleplay:
[Prospect] “I own six flower shops that specialize in large event decorating.”
[Sales] “You specialize in large events. Why did you choose that niche?”
[Prospect] “Lower overhead. I can work out of a warehouse rather than a storefront. I don’t have to maintain perishable stock; I order in large quantities only when needed, which keeps my prices down.”
[Sales] “What do you mean by large events? How would you define that? What are the minimum orders?”

4. Use the prospect’s industry jargon, if appropriate.
If you’re talking to an expert, show your expertise by sounding as if you’ve spent your whole life in his industry. If you’re talking to a neophyte, don’t embarrass him with your technical jargon. This is especially true in retail sales in which customers look to salespeople for guidance, not confusion.

Every field has its own jargon, and you may be an expert in yours; however, your prospect may not be as well versed as you. Avoid questions that will confuse your prospect or worse, make him feel inferior.

Example question not to ask: “Was the baud rate of your present system satisfactory?”
Example question to ask: “Were your telephone transmissions of data fast enough?”

5. Keep questions simple.
If you want useful answers, ask useful questions. Convoluted or two-part questions should be avoided. Ask straightforward questions that cover one topic at a time. It’s best to ask for one answer at a time.

Example question not to ask: “What do you think about the marketing plan and will the new ad campaign confuse customers and would that confusion actually be beneficial to the long-term product growth?”

This will not produce a meaningful answer. If you ask a two-part question, people tend to either answer the second part only or only the part they were interested in or felt safe with. One question at a time!

6. Use a logical sequence for your questions.
Prospects like to know where your questions are headed. If they can’t tell, they may suspect you’re manipulating them. By following keywords and asking questions in a logical order, you will keep your intent clear and build trust.

7. Keep questions non-threatening.
Start off safe, general, and non-threatening. That means asking open-ended questions that don’t touch on sensitive subjects. Later, after you have built up trust – and when it is appropriate — you can ask about financial ability, business stability, credit rating … anything relevant.

Example questions: Here’s a post that highlights seven questions one sales rep uses to ask more intense questions in a light and friendly manner.

8. If a question is sensitive, explain its relevance.
It makes sense to justify a sensitive question to your prospect. After all, she has a right to know why you are asking.

Example questions: Here’s a post on how to ask sensitive sales questions without upsetting your prospects.

9. Focus on desired benefits.
Many prospects will not know all the benefits of your product or service. Therefore, don’t ask them what benefits they are looking for; tell them what benefits will be theirs! When you ask them what they want, have them generalize about the improvements they would like to see.

If you were to ask a prospect, “How do you expect a computer to streamline your office?” you may make her feel ignorant. She has never owned a computer, so she probably has no idea of all its uses. It would be better to ask what general improvements she would like to see.

Example question: “What are some of the duties in the office that you find tedious and time consuming?”

This will free her of needing computer knowledge to answer the question. She’ll answer: “The payroll, accounts receivable, accounts payable,” and so on. You’ll then have the information you need to recommend the hardware and software.

10. Maintain a consultative attitude.
Remember, you’re a liaison between your company and your customers; you are a consultant. As such, you want to question your prospect in a way that will yield the maximum amount of information with the least effort. To do so, take the pressure off the questions. Ask them in a relaxed tone of voice. Give time for the answers, even if it means sitting quietly and waiting. Don’t be in a hurry to get to your next appointment. The investment you make in time now will pay off handsomely when the prospect evolves into an annuity.

How do you ask your sales questions so they’re effective? I’d love to hear more tips!


Dr. Tony Alessandra Dr. Tony Alessandra is a behavioral and communication expert, and author of 29 books including The Platinum Rule, Collaborative Selling and The Art of Managing People. Today he is a leading business motivational speaker on communication, customer loyalty and sales.

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