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50 Powerful Sales Questions

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Written by Mike Schultz
President, RAIN Group

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Great sales questions help you find out what’s going on in your buyer’s world. They help you connect with buyers, understand their needs, understand what’s important to them, and help them create better futures for themselves.

They help you disrupt buyer thinking and change buyers’ perception of what’s true and what’s possible. They help you drive the sale forward and avoid pitfalls that can derail the sale along the way. 

Great sales questions help you win sales.

Here we share 50 powerful sales questions that'll put you on the path to building rapport, navigating buyer wants, needs, and desires, and ushering sales to the close.

What Are Open-Ended Sales Questions?

An open-ended sales question is a question with no definitive answer, aimed at prompting a longer or more insightful response from a buyer. Open-ended questions can be further divided into broad and specific questions.

Broad open-ended sales questions 

Broad open-ended sales questions get people to open up and start talking. They’re great for helping you find out what's going on in your buyers’ world and are essential to sales success.

Examples of broad open-ended sales questions include:

  • “What’s going on in your world these days?”
  • "Can you give me some background on what’s happening in your division?”
  • "Thinking about HR at your company, where do you see the areas of opportunity for improvement?”

Specific open-ended sales questions

Specific open-ended sales questions are more exploratory. Some buyers might not share much information when you ask broad open-ended questions, or they might not know the answers. These questions uncover latent needs the buyer might not even be aware of.

Specific open-ended questions yield one of three answers: an expression of need, no perception of need, or lack of knowledge.

Examples of specific open-ended sales questions include:

  • “You’ve mentioned that you’d like to improve your company’s efficiency. There are a lot of ways to go about this. Let’s start with billable hours. How closely do your monthly actual numbers align with your projected numbers?”
  • “What about staffing? Do your current employees have the skills needed to move the company forward? Where are the knowledge gaps?”
  • “What would you like to be doing that you just don’t have the resources to tackle right now?”

Good open-ended sales questions help you connect with buyers personally, understand what's important to them, reshape their thinking, and create better futures for them. The importance of asking the right questions cannot be overstated. (Hint: you need to ask more than, "What keeps you up at night?")

The idea is to move from general to specific questions, uncovering the buyer’s own perceptions of their needs, helping them to express a broader set of needs, and discovering enough information so you can present ways to improve that drive the buyer’s interest and the desire to act.

What Are Closed-Ended Sales Questions?

Closed-ended sales questions are great for diagnosis. Whether you get a “yes” or a “no” answer, it’s easy to follow up and get the buyer to elaborate. By asking closed-ended questions you can uncover needs that buyers may not yet perceive as a problem, but when you ask so specifically, they sometimes reconsider.

Examples of closed-ended sales questions include: 

  • “Do you feel like you’re hiring the best people fairly consistently?”
  • “Are you getting the pool of candidates you want when you’re looking to hire, and are you getting them fast enough?”
  • “Do you feel like you waste a lot of time sifting through the also-rans to get to the highest potential candidates?”
  • “When you make offers, do the best candidates accept them as often as you would hope?”

Open-Ended Questions for Sales

Below are 50 sales questions you can use in your sales conversations. The open-ended questions for sales are grouped based on our RAIN Selling framework for leading sales conversations: Rapport, Aspirations and Afflictions, Impact, and New Reality.

Also included are questions for insight selling that you can use to get buyers to think differently, and questions to help you drive the sales process forward.

One thing you’ll notice about these sales questions: they don't need to be complex. Oftentimes the basics are all you need.

Tip: These questions are not a complete roadmap for a conversation with buyers. Explore questions as needed and be sure to listen to what your buyer has to say before launching into the next question.


Sales Questions to Develop Rapport

Before buyers will open up to you about their needs and desires, they have to be comfortable with you.

Comfort (and trust) begin with rapport.

Building rapport is sometimes dismissed as a ploy to make a superficial connection with a buyer. You shouldn’t make superficial connections; you should make genuine ones. Genuine rapport sets the table for the rest of the conversation.

7 Open-Ended Sales Questions to Build Rapport 

  1. What did you do last weekend?
    Questions about off-work activities give you insight into what matters to your buyer. You’ll learn about kids, pets, hobbies, passion projects, and more. People appreciate it when you ask about these things during subsequent conversations, too.
  2. What’s going on in your business these days?
    Asking about business in general seems broad, but buyers will often rattle off a few things that are most important to them, giving you ideas for cross-selling and up-selling later. It also shows buyers that you’re curious and want to know what’s going on beyond your particular sale.
  3. How have things in your business changed given [insert an industry event]?
    Industry-impact questions demonstrate your familiarity with and interest in the buyer’s business beyond simply stating, “Yes, we’ve worked in [industry].”
  4. It was good to hear the short version of your background at the meeting, but since we’re out for lunch, I’d love to get the long version. What’s your story?
    People love talking about themselves. If you’ve already done the 20,000-foot-overview talk, asking for more details shows you’re truly interested in learning more (but only if you do it genuinely).
  5. I have to say, I really like the way you don’t just have your values up on the wall like every company, but you have all the comments from your team about what the values mean to them. How did you all come up with that? I’m guessing you learned a lot about your company and team. Thoughts?
    Knowing your buyer’s leadership style and more about the company’s culture will give you a better idea of how to communicate with the team during the sales process and when you start working with them. It also shows that you’re attentive and genuinely interested in them. This is just an example—the idea is to ask about something that truly intrigues you.
  6. You mentioned you want to retire in a few years. What are you thinking of doing then?
    Like the weekend question, a question about the buyer’s future will help you understand what’s important to them and what they’re passionate about when they’re not working. It will help you relate on a personal level and find common ground. After all, people buy from people they like.
  7. What were you doing before you were at this company?
    Your buyer’s career path may come in handy because it will give you a sense of where they’ve been and where they’re headed. In some cases, you may discover that a buyer pivoted in their career, which is a great opportunity to ask more questions.


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Sales Questions to Discover Aspirations and Afflictions

Most sales advice suggests that you must first uncover the “problem” or “pain”—afflictions—to sell products and services as solutions to needs.

This advice too often drives sellers to employ find-out-what’s-wrong-and-fix-it thinking.

The sellers most successful at creating opportunities also focus on the positives—the buyer’s goals, aspirations, and possibilities the buyer doesn’t even know exist. You must ask questions that uncover both aspirations and afflictions.

10 Open-Ended Sales Questions to Uncover Aspirations and Afflictions

  1. If, at the end of this hour, you looked back and thought ‘that was an hour well spent’ what would we have covered?
    What better way to run a meeting than to make sure you cover exactly what matters to the buyer? Plus, this question gets to aspirations and afflictions for the meeting, which ensures you’re not only focusing on pain points.
  2. Why isn’t this particular technology/service/product/situation/issue working for you right now?
    Many buyers are willing to talk to sellers because something they’re doing or using right now isn’t working for them. It’s important to know what you’re up against.
  3. Many of our clients report problems with A, B, and C. How are these areas affecting you? What do you think about them?
    This is another great way to establish expertise and industry credibility. It also asks the buyer to think about their challenges in a different way or consider challenges they hadn’t identified previously. The idea is to ask specific open-ended questions that show you know the area well.
  4. What’s holding you back from reaching your revenue (or profit, or other) goals?
    Learning about obstacles early in the conversation is imperative. If the buyer believes an obstacle is insurmountable, it’s up to you to show them why it’s not and how to get past it.
  5. What goals and objectives do you have in general for your business? For this particular area?
    Finding out about your buyer’s hopes, goals, and aspirations allows you to focus on the positives during your conversations and uncover needs the buyer hadn’t previously considered but should.
  6. (Assuming they set the meeting) Why did you ask me to talk with you today?
    You may already know why the buyer set the meeting, but it doesn’t hurt to revisit the question to make sure you’re on the same page. It’s also possible there have been developments since the meeting was set, so it’s useful to see if there are any updates.
  7. (Assuming you set the meeting) As I mentioned earlier, I’d like to share a few ideas that have helped our clients succeed in the X, Y, and Z areas. Before we get going, by the time we’re done with this meeting, what else might you like to cover?
    It’s possible the buyer had something else in mind when they accepted the meeting with you beyond your intentions. This is a good way to check in before you start talking to ensure the meeting is as valuable as possible.
  8. What’s your sense of what needs to happen to improve that/make progress here/change that?
    Knowing your buyer’s perspective on the situation and how they think it can be addressed will give you an idea of things like company culture, how receptive they’ll be to your ideas, how to frame your solution/service/product, etc.
  9. What kind of opportunities do you see for improvement in this area?
    This is a great question to uncover both aspirations and afflictions. By getting the buyer to articulate the opportunities for improvement, they're likely to talk about both the problems they have in this area (afflictions) and their vision for what it could be like (aspirations).
  10. What have you done in the past to address this issue/try to reach this goal?
    As you’re formulating your solution, you don’t want to suggest something the buyer has already tried and failed. You either want to build onto what they’re doing or change it altogether, neither of which you can do without this question.

Sales Questions to Demonstrate Impact

You must demonstrate to the buyer how working with you is going to improve their world. What are the personal implications? Business ones? Help the buyer see the impact of your work together.

6 Questions to Make the Impact Case in Sales

  1. If you could overcome these challenges, what would happen to your company’s financial situation?
    You need to get the buyer to quantify the impact of working with you. It’s one thing to tell the buyer that, on average, you’re able to save your clients $250,000 in operating costs. It’s another for them to do the calculation themselves and see the impact on their business.
  2. If you were to make this happen, what would it mean for you personally?
    The more of a stake the buyer has in seeing the results realized, the more buy-in you’ll get, and the more likely the buyer is to support you internally. Beyond financial impact, you want to help the buyer look good. For example, maybe your project will help the buyer get the promotion they want.
  3. How would implementing these changes affect your competitiveness in the market?
    Maybe your project will help the company grow market share, become more profitable than competitors, or be more innovative in their market. Whatever it is, you need your buyer to articulate how working with you will give them a leg up over their competition.
  4. What won’t happen if you chose not to move forward with this?
    When urgency to move forward is an issue, ask what won’t happen. The buyer likely already knows what won’t happen, but saying it aloud to you makes it more real. You don’t want to scare the buyer, but creating fuel for action can be helpful.
  5. How do you think the board of directors would evaluate the success of this initiative?
    Knowing the metrics by which your work will be judged is the first step to success. By knowing these ahead of time, you’re able to put systems in place to track them from the get-go.
  6. If you don’t solve [insert the challenge here], what kind of difficulties will you face going forward?
    Again, looking at the cost of inaction can create fuel for moving forward. This question is also helpful as buyers start trying to piecemeal your product/solution.

Sales Questions to Define New Reality

One of the greatest difficulties in sales is helping the buyer understand exactly what they get when they work with you. You need to paint a compelling before-and-after picture of what you will achieve by working together.

You can only do this when you know what’s truly important to the buyer, which is going to be different for each one.

8 Open-Ended Sales Questions to Reveal a Buyer’s New Reality

  1. If you were to wave a magic wand to make it 3 years from now and this all works out, how will things be different?
    Your part of an organization’s 3-year plan is likely a small one, but getting the whole picture will both get your buyer excited about the possibilities and help you see where else you might work together.
  2. (In early sales discussion) You mentioned you’re not having a good experience with your current provider. If you work with us, what are you hoping will be different?
    Especially in your efforts to unseat an incumbent, you want to know what’s not working now to formulate a plan to be different/better. This will also give you an indication of the buyer’s expectations.
  3. (In later sales discussions) Given all we’ve talked about, what do you see as being different if we were to move forward together?
    This question gets the buyer thinking about change and envisioning the future possibilities.
  4. What does success look like for you, personally?
    Having the buyer vocalize how the success of the project would impact their personal life and/or career creates excitement and generates additional buy-in. After all, people buy with their hearts and justify with their heads. You need to appeal to both.
  5. What does success look like for your business?
    It’s important to know how buyers are going to evaluate the success of your initiative. In painting your picture of the new reality, you need to clearly define what that end goal looks like for their business, for them personally, for the project, and for your relationship working together. Don’t make assumptions here. Get the buyer to articulate their future state both from a rational and emotional standpoint. This question, and the next few, help buyers articulate this vision.
  6. What does success look like for this project?
    Establishing success metrics is important before you start, but you also want to make sure your buyer has realistic expectations for the results you can achieve.
  7. What does success look like for us working together?
    Your primary contact is most frequently your Champion—the person who will help you navigate their organization and push the initiative forward. Establishing a strong relationship with them is essential for success.
  8. If there were no restriction on you—money, effort, political issues, and so on—what would you change? Can you tell me why you say that?
    A question like this indicates what’s most important to the buyer in this situation and gives you an opportunity to help them get there even with the stated obstacles in the way.

Sales Questions to Generate Insights

Powerful sales questions can also be used to disrupt buyer thinking and to get them thinking differently. We call this insight selling.

Many people think insight selling is about educating buyers through presentations. They’re about half right, but without the other half, they’re missing out on the full impact of insight selling. 

The missing link is asking insightful questions that disrupt buyer thinking. If you can change a buyer’s perception of what’s true and what’s possible, you can influence their agenda for action.

8 Powerful Questions for Insight Selling Success

  1. Why? (Why is that your strategy? Why do you say that? Why do A vs. B?)
    By asking why, you're asking buyers to justify something. If they can do so convincingly, good for them! But oftentimes they can’t. This opens an opportunity for you to help.
  2. How? (How do you see this panning out? How do you think you need to proceed so this becomes a part of the culture? How might you avoid the common challenges like X, Y, and Z?)
    “How” questions help the buyer start thinking about the new reality. Sometimes they have strong reasoning for why to do something, but they don’t have a strong plan for how to get it done. When you help buyers think about the how, it helps them avoid problems and develop plans that will make everything work better. How questions can be very powerful for generating insight.
  3. What have you tried that hasn’t worked?
    This question will help you understand buyers' thinking and help you see the gaps between what they know won’t work and what you know will.
  4. Have you considered A, B, C, etc.? If not, why not?
    You may find out they did, but didn't approach it right, or didn’t know about a new advancement in the area. Maybe they didn’t know better options existed. You can bring them to the table.
  5. If I said I believe you might have under-invested to achieve this outcome in the past, what would you say?
    When many buyers try to do something the first time, they look to cheaper options. Then those cheaper options fail. This kind of question can push buyers out of their comfort zones. They might say, “Well, what should I have done?” Or, “The ROI wasn’t worth spending more.” Most answers give you opportunity to bring insight to the table.
  6. What do you think is possible? What’s possible for action? What’s possible for solution choices?
    Whatever you find here gives you the chance to alter the buyer’s perception.
  7. How do you know that?
    Here you are testing the buyer’s assumptions. This can be tricky, but thinking critically together helps to broaden their perspective and consider other possibilities.
  8. What do you think is missing?
    Once you open the buyer’s mind to other possibilities, questions like this may spark additional ideas or considerations.

Closed-Ended Sales Questions for Diagnosis

Much sales advice tells you to avoid using closed-ended questions. Closed-ended questions have a time and place and can be very powerful.

Closed-ended questions can be great for diagnosis and ruling things out. After any closed-ended question, use one of the follow-up questions to get the buyer to continue talking.

4 Closed-Ended Sales Questions to Refine Your Solution

  1. Would you say all your customer service reps are using the technology to its full ability?
    This question is all about finding holes in the buyer’s operational processes and isn’t limited to reps and tech. Replace with “project managers” and “building materials” and you have a different conversation with a different buyer.
  2. Should your team be doing more of X?
    Like many of the questions in this area, if they say yes, you can explore this further. If they say no, you can do the same. Push the buyer with questions that get them to question their initial response.
  3. Do you think you’re doing all you can in [insert area]?
    Maybe they are. Maybe they aren’t. But this question coupled with a follow-up question will challenge them to deeply consider their efforts.
  4. Do you think [insert area] is a problem for you?
    If they say yes, you can explore. If they say no, same thing. You can push them with questions that get them to question their initial response. As the expert, you’ve seen what problems other companies in their space have. This question both establishes you as knowledgeable about their industry and exposes potential pitfalls.

Follow-Up Sales Questions for Elaboration

Follow-up questions provide a power boost to your sales questioning.

These three open-ended questions alone can instantly uncover a remarkable amount of valuable information.

3 Open-Ended Sales Questions to Keep Buyers Talking

  1. How so?
    Understanding the buyer’s perception of a situation will not only give you further insight into how to address it, but also a glimpse of the buyer’s thought process.
  2. Can you tell me a little more about that?
    Whether you don’t understand, want to know more, or think there’s an opportunity in this area, digging a little deeper will give you the clarity you need.
  3. Why? Yes, this is listed twice (see #32).
    Asking “why” a few more times can open the door for new insights as you get to the underlying cause of the problem. This allows you to create a better, more durable solution.

Process, Page, and Perception Sales Questions

There are four kinds of sales questions: problem and possibility, process, perception, and page. We’ve already covered problem and possibility. To win sales, you also need to know what the buying process is, what the buyer’s perceptions are, and whether you’re on the same page.

4 Questions for Buyer Alignment

  1. (Process Question) If we get to a point where we move forward together, who on your side would need to be involved to make sure we can get this project underway?
    If your contact isn’t a decision maker, or is only one of a team, this is where you find out who the other players are and work on getting in front of them.
  2. (Page Question) We just covered X, Y, and Z over the last 15 minutes. To summarize the key points [insert summary here]. Did I capture the essence right or am I missing anything?
    This is a good practice for any meeting to ensure everyone is on the same page but is especially important in sales to confirm you understand the buyer’s situation correctly.
  3. (Perception Question) Just checking in as we’ve been working on this for a few weeks now. How are you feeling about how things are going? Are we on the right track?
    While you may think things are going smoothly, the buyer may have a different idea of how things are going right or wrong. Asking this regularly allows you to stay on the right track or course correct if necessary.
  4. (Perception Question) Is there anything not sitting well with you? With our process, our offering, how we’re interacting...anything that gives you pause about moving forward?
    Again, this will give you an idea of the buyer’s perception of how things are going, but also may uncover hidden objections.

The Best Sales Conversations Balance Advocacy & Inquiry

Sometimes all you need is to ask one question and the buyer will share all the information you need to help them. More often, you need to make several lines of inquiry. Don’t overdo it, though. You don’t want to make your buyers feel as if they're on the witness stand.

Don’t forget that the most powerful sales conversations tend to balance inquiry (asking questions) with advocacy (talking, educating, giving advice).

Coupled with strong advocacy, the 50 sales questions shared here will help you connect with buyers, uncover needs and opportunities, communicate the impact, and demonstrate your value by pushing back and getting buyers to think in new ways.

These are all essential elements to winning sales consistently.

Last Updated June 27, 2024

Topics: Sales Conversations