<script type="application/ld+json"> { "@context": "https://schema.org", "@type": "FAQPage", "mainEntity": [{ "@type": "Question", "name": "How can we use sales questions to uncover a prospect’s pain points?", "acceptedAnswer": { "@type": "Answer", "text": "Asking the right questions can help you identify a prospect's pain points and understand their needs better. Some examples of sales questions that can help you uncover a prospect's pain points include: \"What challenges are you currently facing?\" \"What problems have you tried to solve in the past?\" \"What impact do these challenges have on your business?\" \"What are some of the biggest obstacles preventing you from achieving your goals?\"" } },{ "@type": "Question", "name": "What are some of the common mistakes to avoid when asking sales questions?", "acceptedAnswer": { "@type": "Answer", "text": "When asking sales questions, it's essential to avoid common mistakes like asking leading questions, interrupting the prospect, or asking too many closed-ended questions. Instead, focus on asking open-ended questions that encourage conversation and provide the prospect with an opportunity to share their thoughts and feelings. It's also important to actively listen to the prospect's responses and show empathy and understanding throughout the conversation." } }] } </script>

55 Killer Sales Questions to Ask to Close More Deals

table of content

55 of Best Sales Questions You Need to Ask to Win Big

It’s no secret that sales is built on personal and customer-centric relationships for not just B2B, but also B2C companies. 

Today’s buyers are complex. Modern-day buyers require modern-day solutions to solve their pain points. To get to the bottom of your buyer’s vessel and convince them to purchase your product, it is imperative to ask great sales questions. 

These open-ended sales questions help you connect with buyers, understand their needs, learn what’s important to learn, and help you personalize your sales pitch.

Sales questions help you disrupt the buyer’s thinking process and shift their perception of what’s possible and what’s not. 

Excellent sales questions help you win deals. 

This blog post will help you to ask the right sales questions to close a deal. 

But first, what is sales?

What Do You Mean By Sales?

By definition, “sale” is a term used to describe a transaction between a company providing a service, or goods to a buyer in exchange for money. 

Organizations have several sales teams that are typically broken into sub-teams based on the region, product, or service they’re selling to, and the target customer. 

To facilitate a sale, salespersons usually reach out to contacts or target customers that might be either interested in purchasing a product that fulfills their problems or directly looking for a similar company that sells a solution. 

Many sales teams are typically measured by quotas or benchmarks for converting leads to customers and closing deals. However, the real goal of sales must be to solve your customer’s problems. 

What are Open-Ended Questions in Sales?

Simply put, open-ended questions elicit an answer that does not end with either a yes or no, but rather requires more thought, typically more than a one-word answer, leading to a conversation. 

Open-ended questions in sales are essential to success. 


Because they allow reps an opportunity to learn more about their prospects and build a rapport, whilst uncovering their pain points, establishing their needs, and offering a clear solution for the same. 

These open-ended questions can be used anytime during the sales process right from the initial conversation up until closing the deal. 

A few features of open-ended questions in sales look like this - 

  1. They are conversational. 
  2. There is no formula for the type of questions asked, as long as they are designed to get more information from the buyer. 
  3. They question the buyer’s ability to answer. 
  4. They usually involve the five Ws - Who, What, Where, When, and Why. 
  5. They are naturally subjective, and not objective. 

When used in sales, these open-ended questions enable sales reps to create healthy dialogue and learn important information about the buyer and their organization. 

Open-Ended Vs Closed-Ended Questions 

Typically, leading a sales call with questions such as “Do you have any questions?” does not elicit any reasonable response due to the nature of the question, because it is a close-ended question. 

Sales reps might get away with these questions but if the answer is no, then the conversation momentarily stops there. 

What’s more, you might have opportunities to dive deeper into their pain problems, leading to failure to establish a rapport. 

But instead, if you ask - 

“What questions can I answer for you?” 

You might end up extending the conversation much more than a closed-ended question did. The buyer might ask you a dozen more questions since it makes them think and in turn, allows you to ask them more exploratory questions to dive deeper. 

This table is a simple low-down on how an open-ended question should begin vs. a close-ended question - 

Open-Ended Questions Close-Ended Questions
What Is/are
Why Do/did
Where Would/will
When Could/can
Who Have/has

Asking open-ended questions has three primary benefits - 

  1. Builds trust 
  2. Demonstrate real interest that makes them feel more engaged 
  3. Gives you more insights and qualitative data 

Let’s take a look at what kind of open-ended questions to be asked - 

55 Killer Sales Questions to Ask to Close More Sales Deals 

A proper analysis requires probing deeper into the buyer’s mind and getting to know their agenda better to provide the best-suited solution to them. 

This requires asking open-ended questions to help focus on questions that allow you to dive deeper. 

There are four levels of open-ended questions to gather more information throughout the sales process - 

  1. Level One: Getting to Know the Prospects 
  2. Level Two: Gathering more background information 
  3. Level Three: Qualification by eliminating doubts and concerns 
  4. Level Four: Closing the deal

10 Open-Ended Sales Questions to Build Rapport 

#1 How are you currently managing your day-to-day activities?

This type of sales question allows you to understand how your prospect manages their day-to-day activities. In the beginning phase of the conversation, the sales rep might not be very comfortable sharing everything with a sales rep. 

This puts them at ease by helping them delve deeper into their everyday processes while opening the door to surface any potential bottlenecks your company can solve. 

#2 What are some of the biggest challenges you face in your day-to-day?

This sales question helps you as a sales rep to open the floor to dive deeper into your prospect’s pain points. You could also frame a follow-up question to focus on a specific challenge they could be facing. 

#3 How have things changed in your business after (insert a business event)?

Although asking about your buyer’s business seems broad, and sometimes even looks a tad bit artificial, industry-impact questions demonstrate your familiarity with the buyer’s business beyond simply stating, “Yes, we’ve worked in the [industry]”. 

#4 How do you evaluate vendors in this (insert industry)?

Understanding the process of how your buyer evaluates their vendor is not only important but also presents an opportunity to benchmark yourself against your competitors. Gaining insights on this can help you improve your product, tackle the pain points, and sell better. 

#5 What deadlines have you currently set for yourself?

Add urgency to your conversation by explicitly asking your buyer if they have set any deadlines against themselves. Once you learn that they have set a date where they must achieve a certain milestone, you can highlight your product as a tool for getting them there more quickly. 

#6 Which resource could you use more?

This is a classic question to uncover your prospect’s challenges. 

This question puts a solution to their pain point. Most times, your buyer won’t even know that it is a pain point until you help them uncover it. Sometimes, they might be used to dealing with certain challenges and not bringing them up. Asking this question forces them to acknowledge their problem. 

#7 What were you doing before you were at this company?

This question might seem a tad bit off-handed but learning your buyer’s journey may come in handy because it will give you a sense of where they are headed. In some cases, you may discover that your buyer has pivoted careers, which is a great opportunity to ask more questions. 

#8 What is the one thing you wish you could improve in your current process?

At times, buyers may feel that their current process is working smoothly for them. And for some, they might end up discovering a better process. In any case, if the answer is that there aren't many improvisations required, this question can help identify areas that need more fine-tuning. 

#9 What are some specific things that are currently stopping you from reaching your goals?

Perhaps it’s the budget, time, or shortage of employees. 

Regardless, this question is important information to consider in your sales process. Sales reps should have a clear get-go of the process right from the beginning and having a deep understanding of your prospect’s potential roadblocks helps you sell your product more creatively. 

#10 What are your desired outcomes?

This question prompts your buyer not to think in terms of goals but rather, the outcomes. 

The urge to tick off a checklist to achieve a goal is one thing but having the desired outcome is a thing altogether. 

For instance, if you are selling a product, your customer’s goal might be to solve X's problem with your solution, such as reducing the ticketing time up to 40% when a customer tries to contact the support team. You can then describe how your product will solve its pain point to achieve the desired outcome. 

10 Sales Questions to Discover Afflictions and Gather Background Information

Most sales playbooks suggest uncovering the “problems”, or afflictions as the first step to selling your product effectively. 

This style of sales training often drives sales reps to “find-out-what’s-wrong-and-fix-it” thinking. 

Although there is nothing wrong with this approach, sales reps that focus more on the positives - buyers’ goals, aspirations, and possibilities are more successful at creating opportunities. 

#11 What have you done to address your challenges so far?

This question will help you understand if your buyer has already talked to similar solutions as your product and uncover their road to challenges, and if answered in your favor, will lay out on a silver platter all the reasons your solution is viable to other competitors. 

This also helps you understand what hasn’t worked for your buyer in the past so you can propel these concerns about these failures from happening again. 

#12 How would changing this process make your job easier?

As a sales rep, it is vital to understand what buyers prioritize in their roles and individual goals. Keeping that in mind, you can then curate your product’s messaging in a way to show how your solution can empower the buyer and take them closer to achieving their goals. 

#13 What does your ideal process look like?

While this kind of question might not always lean towards what you might be expecting, it gives clarity on what your buyer might be looking for when they approach a vendor such as yourself. 

It also allows jotting down your roadmap, introducing new features, which might be more of a “want” than an “immediate need”, or even opening doors to including additional product features in the deal. 

#14 Why isn’t this particular technology/service/product/situation working out for you?

A lot of buyers are willing to talk to sellers without having an agenda for purchasing the solution. Sometimes, it works in your favor since you learn what you’re up against, and also, understand how you can close the bridge. 

#15 Many of our existing clients report problems with X, Y, and Z. How are these areas affecting you and what do you do about it?

Asking this is a great way to establish industry credibility and expertise. It also allows the buyer to think about their challenges in a different way or consider challenges they hadn’t previously. 

#16 What goals and outcomes do you generally have for your business, for this particular area?

Learning about your buyer’s goals, objectives, and desired outcomes allows you to focus on the positives during your conversation and thus, uncover the needs required to reach their goals. 

#17 What do you perceive as your team’s greatest strengths? 

When having a sales conversation, it is considered rude to ask your buyer about their weakness as the first point of interaction, so start by asking what their greatest strengths are. 

Then, go after their weaknesses. This way, you will learn what the team could be doing better and how your product will benefit them to fit into their potential improvement plans. 

#18 From your perspective, what do you recognize your needs to be? How important are they?

A far better alternative to, “What are your needs?”, this question will pinpoint your customer’s perception of their needs. 

Once you ask a couple of need analysis questions, you will likely have a better understanding of your customer’s needs than they do. 

#19 Why did you agree to speak with me today?

Regardless of who set the meeting up, it doesn’t hurt to revisit the question to ensure you’re on the same page and also uncover the reason why they actually want to talk to you. 

It might be because they want to learn about a quick solution, or they might be assessing you vs your competitors, or there might be something more. This question helps you learn about the developments the buyer has made since the meeting was set up, so it’s useful to see if there are any updates. 

#20 What kind of opportunities do you see to notice an improvement in this area?

This is a great question to uncover both aspirations and afflictions. 

By getting the buyer to speak up about the opportunities for improvement, they’re highly likely to talk about both the problems (and possible afflictions) in this area and their vision for what the solution could bring to the table (aspirations). 

6 Sales Questions to Ask During a Sales Conversation to Eliminate Doubts 

At this stage, you’ve most likely established a need to purchase your product with your buyer. 

This is the right way to get into the process of implementing what a product or service would look like. 

#21 Have you considered other vendors? How are you evaluating different options?

Having a good knowledge of who your competitors are and who your buyer is considering might be an advantage to you. 

Narrowing it down by knowing the nitty-gritty of who exactly the competitors are by hearing directly from your buyer helps you focus and attack with depth rather than breadth. This also gives you a chance to focus on your competitor’s differentiators to make an overall good choice. 

#22 What would implementing our product look like at your company?

As you begin building out a final proposal for your prospect, it is also vital to understand how your buyer would leverage your product to their advantage. 

For instance, if you sell by-products, their adoption will determine how impactful your solution is. This will, in turn, inform how you structure the deal and also explain the onboarding process to your buyer. 

#23 Which features do you consider must-haves and nice-to-have?

As a seller, you might think you have covered all bases. But only once you talk to your prospect, do you discover features that are either missing from your product or needs improvement. 

#24 What motivated you to search for a solution now?

Typically, most prospects face a challenge for months together before finally looking for a solution to address their pain point. Asking this question will help you overhaul your current process, so such buyers stumble upon your product much earlier. 

#25 Who are the people who have a final say in the decision-making process?

If it is a big enterprise, chances are, there are multiple-level decision-makers you might have to deal with before finally closing the deal. Ensure you find out who gets to say yes in the final decision-making process through your discovery calls. 

#26 What are your buying criteria and KPIs?

This question prompts your customer to describe the factors that lead to choosing the product in their organization. As a follow-up question, ask them what their success KPIs look like - it might range from gaining more customers, retaining an old customer, or even simply just passing through the sales funnel. 

7 Sales Questions About Understanding the Buying Process 

This stage is the one where your team has progressively moved forward with their sales process. These questions will help you understand what the buying process is, and how to qualify your leads. 

#27 How does your company evaluate the potential of new products? 

If you want to be a champion in your niche and know how to sell your product better, then you must learn how your potential buyer evaluates a product before purchasing it. The primary benefit of asking this question is that it is open-ended, so, the customer can talk about anything - they’re not forced to give a specific answer. 

#28 What level of service are you looking for?

Does your buyer need an easy solution - a plug-and-play kind of product so they can start using it straight away? Or, do they need an extensive support team? 

Knowing the depth of service they might require will help you gauge their needs once onboarding is completed. 

#29 What factors do you like about your best supplier? What don’t you like?

Even if your buyer’s best vendor might not be relevant to what you sell, it is important to ask this question to find out how your buyer benchmarks the level of service received from the vendor. 

You might not always replicate the same characteristics as them, but by finding out what they like and what they don’t, you can easily understand how your product can fill the gap. 

#30 What might cause you to change your current vendor?

Regardless of how good a B2B business might be, customer churn is a real concern. 

And so, naturally, you want to cover all bases right from the get-go to understand what would actually cause your customer to churn. If they don’t have an answer, maybe try asking, “What caused you to leave a supplier in the past?” and voila, there’s your answer. 

#31 What does success look like for us working together?

Your primary contact for all your sales conversations is your champion - the person who will act as a guide to help you navigate your organization and push the initiative forward. 

Establish a rapport with them and learn what success looks like for them, and try to follow the path to success. 

#32 Are there any obstacles that could prevent this deal from happening?

Make sure to only ask this question when you are in a stage of almost closing the deal. Knowing all the potential roadblocks can help you act proactively instead of reactively, to close the deal faster. 

#33 How do you usually reach purchasing decisions?

Some organizations set up a team-wide meeting to weigh in on the solution with a poll, or pros and cons, and some evaluate the pricing and what benefits the product brings to the table. 

If you are selling a cheaper product with must-have features, then your purchasing process might be really fast, whereas, if your product is on the pricier side, the process might be different. 

5 Sales Questions to Demonstrate Impact 

Demonstrating to your customer why using your product will change their world is vital. What are the personal implications? How will impact the business? 

#34 If you could overcome your primary challenges for your issue, what would happen to your company’s financial situation?

Help the buyer quantify the impact of working with you. It’s one thing to make your buyer understand that, but if you help them oversee the fact that they are saving XXX dollars in operating costs by calculating the cost themselves, that is more impactful. 

#35 What won’t happen if you chose to not move ahead with our product?

When there is an urgency to move forward with your solution is an issue, ask them what won’t happen. The buyer most likely already knows that but saying it aloud helps you uncover the issue yourself. 

Don’t scare the buyer, but creating fuel for action can be helpful. 

#36 If you don’t solve [insert challenge], what kind of difficulties will you face moving forward?

This question helps you discover how your buyers start trying to piecemeal your product/service. Again, looking at the cost of inaction can create an actionable step for moving forward. 

#37 What product features would lead to a purchasing decision?

Some product features might not be absolutely necessary for your customers, while other features might be critical. Whatever your buyer mentions here, use that to highlight the exact benefit they get from your product. 

#38 Would you rather cut costs, and productivity, save money, or improve the impact?

This question is another way to uncover your customer’s priorities. The positive part of this question is that it offers a “Would you rather” format, making it easier to ask and leading to a more conversational answer. 

7 General Open-Ended Sales Questions to Ask on a Sales Call 

#39 Which departments are involved?

Is it the sales team, product team, or marketing team?

While selling to large organizations, it is important to know how many departments are involved, and what stakeholders are directly involved in making a decision. 

#40 Who oversees the budget?

You may have uncovered this question while gauging who the final nay-sayer is in this particular process. But if you still haven’t identified that one particular person giving a nod for the budget, or the department responsible to say yes to you, now’s a good time to ask. 

#41 Do you currently have a contract with another solution? If so, when is it up for renewal and is there a cancellation fee?

This helps you understand if your buyer has already dipped their toes in a similar solution as yours. If they currently have a contract, you have to convince them to make the switch. However, if they are not interested, be patient and follow up regularly. 

#42 Based on what we’ve discussed, do you think our solution is a good fit for your needs? If so, why?

At this point, you would be a better judge to understand if your prospect is qualified and if they are viable to be pushed further down the funnel. Now’s your chance to re-confirm their interest and handle their objections. 

#43 On average, how long does it take for your team to purchase a product?

Ask this question to your advantage to find out how long you could potentially be in the sales process, and how long it will take to finally close the deal. 

#44 Do you think you’re doing all that you can in [insert area]?

Sometimes, your buyer thinks they’re doing all that they can, and sometimes, they aren’t. Asking this question will help them foresee their current process and couple this with a follow-up question to challenge them deeply. 

#45 Do you think [insert area] is a problem for you?

If they say yes, then explore this question further. Even if they say no, do the same. 

Push them with questions that get them to question their initial response. As an expert in your niche, you are aware of such problems existing with the other companies you have worked on. This question helps you establish your hold on the subject of the industry and expenses and any potential pitfalls. 

5 Sales Questions to Discover Buyer Alignment

To win sales deals more often, you need to know what the buyer’s intent is, and if it aligns with your questions: process, page, perception, and possibility. 

#46 We just covered A, B, C, and D in the last 20 minutes. To summarize the key points, did I capture the agenda of the call right or am I missing anything?

This is a good practice to ensure that everyone involved in this deal is on the same page but especially important before closing the deal to understand the buyer’s situation, expectations, and intent correctly. 

#47 Is there any aspect that is not sitting well with you? With our offering and process, is there anything that you want to pause before moving forward?

This will give you an idea of the buyer’s perception of how things are going, but also helps you re-confirm the factors that you are offering as a solution so the expectations are matched correctly. 

#48 Just checking in since we have been in conversation for a few weeks now. How are you feeling about how things are going? Are we on the right track?

It’s normal to think that you are heading in the right direction and even get excited about it but, sometimes, the buyer might have a different idea of how things are going and if they’re wrong or right. Asking this regularly helps you stay on the right track and course-correct, if necessary. 

If you use a sales intelligence tool such as Salesken, you can refer to cold-calling scripts to always stay on track and impart the best practices to help you close the deal quickly. 

 #49 How so?

Understanding the buyer’s perception and aligning that with your organization’s goals. This will not only give you deeper insights into how to address the buyer’s issues but, also gives a glimpse of the buyer’s thought process. 

#50 Can you elaborate more on that?

Digging a little deeper into this area will only help you qualify your lead further. Regardless of your understanding of their conversation, may want to learn more, or think there is an opportunity in this area, elaborating on this will help you in the long run. 

5 Sales Questions to Close the Sales Conversation 

At this point in the sales cycle, you want to be sure of covering all bases and that everyone on the team is on the same page, so bring in those additional buying committees and decision-makers. 

These questions will help you structure your closing proposals for various stakeholders across the organization. 

#51 How will the decision-making process look like?

It is vital to understand how your prospect buying committee functions. 

You need to learn how the decision-making process works, what stakeholders are involved, and what you can provide from your end to make it run smoothly. 

#52 If we could find a way to deal with the [objection], would you sign the contract [on date/time]?

Often, objections kill deals. But in your case, make sure that you handle the objection in a way that actually will lead to closing the deal. Of course, this is also directly dependent on the company’s ability to compromise and resolve the problem by a given date. But fix this, if it is possible, and getting the customer to agree ahead of time is a clever way of closing the deal. 

#53 If we throw in [insert freebie], would that convince you to close the deal?

As expected, this closing technique does not work all the time and isn’t appropriate for every situation. 

But for large enterprises or very large deals, offering an exclusive feature or an add-on to sweeten the pot might be a smart move. 

Price discounts could also be a closing factor in competitive markets. 

#54 What happens next?

According to sales expert Mike Brooks, “Whenever your prospect begins stalling or providing any other excuse for not acting today, you simply respond with these three words.”

It might seem like a crazy idea but if something is preventing you from making that purchasing decision, and if you can figure out what the reason is, do it now. 

#55 What else can I do to help finalize the decision?

This is where negotiating comes in. 

In any deal that has reached the final stage, the goal is close, and sometimes, it might need a bit of persuasion. Understand what terms the prospect needs and leverage your own internal resources to help them arrive at a closing decision. 

Sales Questions to Ask Your Customer About Your Product 

When checking to cross-sell, or upsell your other products with current customers, it is important you ask the right questions so they do not churn. 

If you fail to ask such questions out of the fear of losing them, you risk missing warning signs they’re unhappy and would consider turning to your competitor.

Close it with these questions - 

  1. On a scale of 1-10, how happy are you with our product?
  2. How likely are you to recommend our product to your peers?
  3. On a scale of 1-10, how comfortable is your organization without our product catering to your pain problem? 
  4. Why did you give us that score?
  5. What exactly do you love about our product?
  6. How has your internal team benefited since adopting our product?
  7. What can we do to help you stay with us for another year?
  8. Would you be interested in our new add-on feature X?
  9. Do you feel you received outstanding customer service?
  10. Can you explain any weaknesses/challenges you have found in our product so far?

3 Sales Questions to Avoid 

Just like how open-ended sales questions help you gain deeper insights and increase sales volume, there are also questions that you need to avoid that might result in a lost deal. 

Avoid questions that are -

  1. Focused on your company (Have you ever heard of us?): These types of questions steer the conversation away from the prospect. It is no longer a conversation, but rather, a one-way interview. 
  2. Loaded/biased sales questions (Are you losing money with your current decision?): This question assumes that your buyer is suffering with their current choice of vendor and your prospect might end up feeling a bit manipulated or pushed into the corner. 
  3. Yes/no questions (Do you like your current vendor?): This type of question is a close-ended question that does not allow your prospect to respond elaborately, but rather with one-word responses, halting the conversation right away. 

Engage in Creative and Delightful Sales Conversations to Close Deals 

Nailing down the kind of open-ended sales questions you ask your prospect is an essential part of qualifying them and closing deals. 

The other part of this process is identifying where, when, and how your sales cycle succeeds and where it needs improvement. 

To create a successful sales process, you as a sales rep must know how to steer the conversation and act accordingly. Sales prospecting questions are exactly that - nailing the conversation and forecasting the process to closing the deal. 

Book a demo with our sales expert today and see how a sales intelligence tool can help you close the deal with easy prompts that require minimal manual work. Get on the bandwagon now!

Frequently Asked Questions

How can we use sales questions to uncover a prospect’s pain points?

Asking the right questions can help you identify a prospect's pain points and understand their needs better. Some examples of sales questions that can help you uncover a prospect's pain points include: "What challenges are you currently facing?" "What problems have you tried to solve in the past?" "What impact do these challenges have on your business?" "What are some of the biggest obstacles preventing you from achieving your goals?"

What are some of the common mistakes to avoid when asking sales questions?

When asking sales questions, it's essential to avoid common mistakes like asking leading questions, interrupting the prospect, or asking too many closed-ended questions. Instead, focus on asking open-ended questions that encourage conversation and provide the prospect with an opportunity to share their thoughts and feelings. It's also important to actively listen to the prospect's responses and show empathy and understanding throughout the conversation.

Don’t forget to share this blog!

twitter logofacebook logolinkedin logowhatsapp logo

Want To See Salesken In Action?

See how Salesken can provide unparalleled insights into every customer interaction