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Ask the Right Questions

When you engage with buyers, it’s essential to get them talking. To do that, ask them questions about their context, reality, and priorities. Here are some great example questions to get you started.

1. Ask about their business

Example: Can you tell me about your business?

This is an extensive question by design. Before you ask this question, tell the customer you’ve done some preliminary research. You previewed their website, looked at their financials, and downloaded several recent articles about their company (if you have done that, and you need to if you have not). When the customer begins to answer, what usually comes to the surface pretty quickly is what’s important to the customer. If you’re selling products to the government, you can substitute the word “organization” for “business.” The beauty of a really good question is that it eliminates all assumptions. It forces you to start with your potential customers, not your products.

2. Ask about the team

Example: Can you please describe the team you have?

Once again, it’s an expansive question designed to get the potential customer talking about what’s important to him. Listen carefully to the prospect’s response to this one. You will be rewarded with how this person feels about and possibly relates to other key people in the prospect’s organization.

3. Ask about their role

Example: What are your responsibilities?

Once you discover the role, title, or position within an organization, probe to find out what a person’s responsibilities are. Here’s where you’ll get a measure of the prospect’s ego, self-esteem, and self-worth. Most salespeople seldom ask this question because they make goofy assumptions based on what they know about specific job titles. In the long run, making goofy assumptions will make you goofy. Ask this question, and you’ll learn more about your prospect than you ever assumed.

4. Ask about their challenges

Example: What are the biggest challenges you face in managing and improving the value of your company's content and data?

This is a terrific question, and the keyword is “challenges.” It’s a positive word that uncovers negative stuff. As a professional salesperson, your job is to identify specific needs and problems. When you first meet a potential customer, it’s not always easy for him/her/they to open up to a stranger about problems, regardless of your sincerity and willingness to help. To speed up the process, focus on “challenges” instead of “problems.” Most people are more than willing to describe their most significant challenges, even if they are reluctant to discuss their problems. Change how you ask the question, and you’ll see how they change how they respond to you. Listen carefully to their response to this question and take good notes.

5. Ask about priorities

Example: What are some of your current priorities?

This question uses only four words. It doesn’t get any easier than this one, and it’s a gem. Here’s what you’ll learn. Some people don’t have priorities, and this question makes those people easy to spot. If they do have preferences, they’ll describe them in detail. If you get a long list, ask the customer to prioritize it. If, on the other hand, the list is small, ask the customer if there are any other priorities. This is an assumption-buster question. If you don’t ask, you probably make too many assumptions about your prospects. The response to this question paves the way for you to tailor your presentation to match the prospect’s priorities. Remember to take detailed notes after you ask this question.

6. Ask about work connections

For example, I see you're Linked to (name ); how are your roles different?

This question will vary according to the situation. It’s a personal question designed to learn about common interests and things that contribute over time to building an intimate relationship. In your research on LinkedIn, FaceBook, Twitter, TikTok, and so on, you’ll notice pictures, trophies, plaques, accolades, and comments on personal interests. Ask any question that advances the relationship to a higher level. Make sure it’s an open-ended question, and you have mentioned that you prepare. Research before reaching out to people and organizations so you don’t waste their time asking questions quickly answered by the prospect’s company website or LinkedIn. “Did you catch that fish?” is the wrong question if you want him to tell you about the prospect’s fishing story. Note: all salespeople are taught in Selling 101 to comment about that “Fish” on the first sales call. Don’t follow that crowd. And stay away from politics and religion.

7. Ask about their environment

Example: What is working best in your current data architecture and environment?

Put your ego aside for this one. Naturally, you want to hear that he/she/they do not like anything about their current [product, service, or solution] environment, and that’s why the prospect has agreed to speak with you. In the real world, however, the prospect probably likes something about their current environment. These are the prospect’s hot buttons. It doesn’t make a difference whether your products can deliver these hot buttons; you must know what they are before setting up the handoff call. Don’t forget to ask the prospect good follow on questions (like the ones in the Extra Extra section below). Don’t assume you know what the prospect means. The two things that kill more sales than anything else are procrastination and assumptions. Avoid them like the plague.

8. Ask what’s not working

Example: If you could change anything about your current vendor, what would you change?

Remember, nothing is perfect! This is a powerful question; if you are patient, you will be rewarded with a good response. Remember this; fifty percent of the time, the prospect’s first response will be: “I can’t think of anything.” Be patient and point out that nothing is perfect. Ask the question again, then wait patiently for the prospect’s answer. No customer is ever 100% satisfied. What you’re searching for is dissatisfaction, no matter how small it may be. Once identified, you have a starting point to build your business case. People are always looking to improve their current situation. Don’t make any assumptions. This is an opportunity question.

9. Ask about their vision

Example: What is your vision for driving change in your organization?

It is incredible how infrequently this question is asked, especially since it’s one of the most powerful questions in the lineup. You’ll discover if your prospect has any criteria. If the prospect has any, she/he/they will tell you what they are. Once the prospect describes the requirements, you can ask to prioritize them to keep the prospect’s criteria top of mind throughout the sales process. The answers the prospect shares tell you what the organization will base its decision on. Ask one hundred different people, and you’ll hear one hundred other answers. How could you begin to understand and convey to the prospect how your product, service, or solution will benefit them without knowing what the prospect’s decision will be based on? Try this one on for size, and you’ll get immediate payback. If the prospect’s response is price or budget, use this follow-up question to set aside the pricing issue. “In addition to price, what other criteria do you have?” It works!

10. Ask about their influence

Example: How do you go about helping a line of the business leader become more data-driven?

The criteria and process are related yet different. You need to know what measures will be evaluated before the decision is made and approval is requested internally at the prospect’s organization. You will also need to know the process involved in making the decision and approval. What steps will the prospect go through to reach a final decision and the approval process once the decisions have been made? You’ll learn whether it will be a toss of the coin or a more complicated process. Either way, you’ll be better positioned to tailor your approach to accommodate the prospect’s criteria and the process they will use. The larger the “deal,” the more important this question becomes.

11 Ask about success measures

Example: How are you measuring success with your current data and management approach?

This is very revealing. Sometimes you will hear things that you couldn’t have imagined. That’s the beauty of the question. There’s no way you can accurately anticipate a response to this question. Ask the question, relax, and listen carefully to the answers you get. This question unearths the individual’s personal and critical measurements for your product, service, or solution. Wouldn’t you like to hear the answer before investing your time and the AE’s time? You’d better believe it.

12. Ask about expectations

Example: What are your expectations when working with an improved product, service, or solution?

This one is very straightforward. Expectations are a powerful and dominant influence. Ask the expectations question if you want to build a long-term customer relationship. If you think you already know, write down the answer as you understand it, then go through your notes of all of your calls and emails from the prospect and see if you know or are guessing. This is a time to question your assumptions and discover what you know and think. Do this, and you’ll be delighted with the results. There are many reasons for asking excellent questions, and only one for not asking them. We don’t ask outstanding questions if we’re in a rush to get to the next call because we want to get the handoff call set up too soon or we are afraid that we know the honest answer and don’t like the real answer.

Updated on June 27, 2023

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