Top 35 Open Ended Sales Questions That Keep Conversations Going (With Examples)

For those of you who follow my work, you are aware of my strong belief in developing an insatiable curiosity that will assist you in becoming innovative, prolific, and successful. In this post, I am going to break down a variety of closed-ended sales questions that you should avoid, followed by 35 examples of open ended sales questions that you should ask instead.

Think of adopting the practice of insatiable curiosity as becoming the equivalent of The Beatles, Steve Jobs, or Michael Jordan in whatever professional context you’re working.

Table of Contents

What Are Open Ended Sales Questions?


An open-ended question elicits an answer that cannot be answered by a yes or no, and therefore requires more thought and more than a one-word answer. These questions usually begin with What, How, and Why.

Some simple examples of open-ended questions are:

  • How are you feeling today?
  • What did you have for breakfast this morning?
  • Why do I need to take these documents with me?

Contrast these with closed-ended questions that can be answered with a yes or no:

  • Do you want pizza for lunch?
  • Are you going to the beach this weekend?
  • Can I help you with that?

Let’s break the difference down even more.

Open-ended vs. closed-ended questions

If you wanted to know if the person on the other end had any questions for you, you might be tempted to ask something like:

Do you have any questions?

You might get away with this if the answer is yes because then they would follow up with another question of theirs.

But if the answer is no, then the conversation momentarily stops right there. You’ll be left awkwardly searching for the next thread or topic. What’s more, you might miss opportunities to set yourself apart from other vendors, or even to gain more information that might prove useful later.

Instead, if you ask: 

What questions can I answer for you now?

You might end up extending the conversation much longer than what a closed-ended question would have accomplished. They might ask you a dozen more questions, which would in turn give you opportunities to ask them more exploratory questions to gain useful insights.

Even if they initially didn’t have any pressing questions, asking them this might jog their minds for more questions that they might not have asked otherwise.

In the context of sales, asking open-ended questions will open up your pipeline in ways you might have not imagined. Read on to see why, plus some examples you can steal for your next sales call.

Related: Using Sales Conversations to Find Product-Market-Fit

Why You Should Ask Open-Ended Sales Questions (3 Benefits)

We’ll start with the three main benefits of asking open-ended sales questions during sales calls rather than making the all-too-common mistake of asking a series of closed-ended yes or no questions.

open ended questions for sales

Benefit 1: Asking open-ended sales questions builds trust

You need to develop an insatiable curiosity in your sales process because this is what will allow you to ask your potential buyers what I call “hyper open-ended questions.”

When you ask hyper open-ended sales questions, you demonstrate to your potential clients that you care about what they have to say.

You open the door for them to tell you precisely what their professional mandates are, what their concerns are, and what they’re looking for.

In short, having an insatiable curiosity and asking open-ended sales questions invite your target buyers to tell you everything you need to know to put you in the best possible position to close the sale with excellence.

The bottom line?

When you lead with open-ended questions, you’re halfway there with building trust with your prospects.

Benefit 2: Demonstrate real interest that helps them feel more engaged

Throughout the process, you demonstrate a real interest and concern for your clients, which helps build rapport and makes it easy for them to tell you the information that will help you close the sale.

Using this technique you remove yourself from the outdated, product-centric value proposition language that drives potential buyers away with its offensive sales stench by choosing to talk instead about what matters most to your buyers.

Maintaining an insatiable curiosity and asking hyper-open ended sales questions helps create a meaningful and professionally relevant dialogue rather than an abrasive sales pitch – this is one of the keys to becoming a modern sales professional working at the cutting edge of today’s marketplace.

What counts today is the ability to move away from a one-sided sales pitch or product demo and toward a dynamic dialogue with potential buyers. Seriously, would you prefer to smell like a sweet fragrance or the inside of a taxicab?

Using hyper open-ended sales questions could be the tipping point towards closing a sale.

Benefit 3: Gives you more insights and qualitative data

Asking open-ended sales questions that start with What, How, and Why will get you more thoughtful and detailed answers that would not have been possible by asking closed-ended questions.

You might even gain some useful insights that would help you close the sale.

Or you might learn some unexpected details that affect the scope and timeline of the project. These details may even determine whether or not the prospect is qualified and a good fit for your products or services.

The conversation may last much longer and that’s a good thing. As opposed to a conversation cut short by “yes” and “no” dead-ends, a longer discussion is a great sign that the prospect is engaged and is willing to trust you.

30 Examples of Open-Ended Sales Questions

This section has a collection of open-ended questions for sales you can use in your next call. Note that you don’t have to use every single question on this list — just use the ones that seem the most natural to you and the conversation.

open ended questions examples

Rapport building open-ended questions for sales

1. What will make this appointment worthwhile for you today?

This open-ended question is a good conversation starter that puts the focus on their needs first. It’s non-threatening, breaks the ice, and sets the tone for the rest of the call. Another advantage is that it instantly sets you apart from the droves of sales reps throwing out pitches right out the gate.

2. What motivated you to take this call with me?

This question helps you learn what the prospect is facing and where their top priority or pain point lies. It also gives prospects a chance to include additional details that might not otherwise have been brought up.

3. How did you get involved in this project?

Getting an answer to this question helps give you some background context as to when the prospect got involved in this project and how. Maybe the prospect just joined the team or maybe they got promoted to the decision-maker level. Depending on how deep they’ve already gotten into the rabbit hole, you’ll get an idea how intimately familiar your prospect is with the project.

4. What’s the most important priority to you in this? And why is that?

As a more pointed variation on questions #1 and #2, this helps you get to the heart of the matter. The prospect’s answer, and their reasoning for choosing that specific answer, will give you a shortcut to closing the deal by placing the focus on their most pressing priority.

5. What is the biggest challenge you face with your business today?

Although this seems like yet another variation on question #4, this open-ended sales question focuses more on the main challenge or pain point that the prospect is experiencing. It may be worthwhile asking about both their priorities and challenges to see if they are consistent with each other.

In cases where their priorities do not align with their challenges, you might have the opportunity to educate them on better or more cost effective approaches to their challenges.

6. What would you like to see improved?

This is where you get a chance to get the expected results straight from the horse’s mouth. Once you get a general sense of their before and after picture, closing the deal is only a matter of connecting the dots in between — as long as your team has the ability and means to deliver the results.

7. I noticed that you just downloaded our ebook entitled “Trends Driving Next Generation Contract Management.” Tell me, what was your purpose of downloading that digital asset?

This question is for a specific situation in which a lead downloaded a digital asset from you. But don’t make the mistake of asking a closed-ended question like “did you find the ebook informative and insightful?”

Rather than a yes or no, their answer to your open-ended question should give you an idea of what was going through their minds when they decided to download your ebook.

Here are some more icebreaker questions that Mailshake came up with: check them out here!

Discovery questions

8. What is preventing you from reaching your objectives?

After asking the rapport building questions, you’ll want to start digging a little deeper into the roadblocks that are preventing them from reaching their goals. It could be budget, lack of resources, time constraints, or something else. Whatever it may be, it is important for sales reps to be aware of their prospects’ roadblocks.

9. What has been working well with your current processes? What has not?

In most cases, there are parts of a process that can always be improved. However, the prospect might want to keep certain implementations in place because those have been working well for them.

As a sales rep, it’s useful for you to know this so you don’t suggest solutions that replace the parts that are already working well. Sometimes a prospect might not be aware of potential improvements, and you can frame the conversation to show how your solution can improve some parts of their process.

10. What measures have you taken to address these challenges?

Oftentimes a prospect comes to you because they’ve already tried to solve their problems internally, but were unsuccessful. You should get information about the approaches they’ve already taken, so you don’t make the mistake of suggesting the same approaches when pitching your solution.

11. If time and money were not factors, and you had full authority, what would you change about your current system?

This open-ended sales question is a great one because it gets their imagination going. By removing time and money constraints, you can get a picture of the results they would be perfectly happy with. From there, you can create a roadmap on how to get there. If you play your cards right, they’ll be begging asking you to take their money.

12. What have I not covered that you would like to know more about?

This is best asked after you’ve spent some time introducing yourself, your company, and your solutions. You might have spent a few minutes talking about what you do and how you can help them, but you might not have forgotten to cover some important points. This is a good stopping point to let your prospect ask you some questions.

13. I have the calendar open right now and we have availability on X or Y. What works for you?

If you need to schedule a product demo after the discovery questions, start by saying “from everything you described to me, it seems the next logical step is for you to meet with one of our contract management specialists.” Then ask them for the best time to meet. This works best rather than asking a closed-ended question such as “would you like to schedule a product demo?”

14. What questions can I answer for you now?

While giving your product demo, check in with the listener occasionally to see if they’re following without using any closed-ended questions. Use this open-ended question rather than what most sales reps ask: “do you have any questions?”

15. I’m going to pause now and allow you to comment

While this isn’t technically a question, you can replace the typical closed-ended question “do you have any questions?” to prompt your prospect to ask you questions or make comments.

That way, the prospect would feel more engaged and listened to, instead of allowing them to abruptly close conversation threads with a “no”.

16. I know I just shared a lot of information with you in this past sequence. I’m going to pause now and allow you to react. What is your reaction to what I just shared?

Instead of asking “does that make sense?”, you should acknowledge that you’ve just shared a lot of information and that you want to see how the prospect feels about it before moving on to the next talking points.

17. Tell me, what sort of outcome can you envision if every sales professional, every month, every quarter, had that sort of power at their hands? How would this impact your business at scale?

This is a twist to #11, which is similar in that this question opens the prospect’s mind for creativity and imagination. A question like this might lead to a lot of interesting conversation threads about how your prospect imagines their business could grow — and get into the specifics about what it would take for that to happen.

Qualifying questions

18. What do you see as the next action steps?

Sales reps who are masters at what they do tend to let the prospect feel that they’re in control of the process, and that the solution — and closing the deal — is their idea. Plus, asking what the next steps also gives you a glimpse into their company’s internal processes and how to navigate them to a deal.

19. What is your timeline for implementing solutions for this project?

It’s important to know how soon your prospect expects the solutions to be implemented, what the hard deadlines are, and whether or not their expectations are realistic. You want to always make sure your timelines are aligned with each other to avoid disappointment or any other potential issues.

20. What kind of budget do you have for this project?

This question deals with potential roadblocks related to budget. By asking this, you effectively preempt the “we can’t afford this right now” objection before the topic of pricing comes up. Getting a number or a range from your prospect gives you the chance to qualify them before proceeding with the rest of the sales process.

21. How does your decision making process work?

It is crucial to know who the players are before you finalize the deal with them. To find out, ask this open-ended question instead of asking something like “do you have a formal decision-making process?”, in which the latter question won’t give you much insight.

22. Who else should we involve in this conversation?

This is essentially a variation of #21 such that it helps you glean insights about their decision making process. But this question also preemptively handles objections such as “I need to check with my manager on this first” just when you’re about to close the deal.

We’ve listed 10 more sales qualification questions to always ask your prospect, so don’t forget to check those out as well!

Open-ended sales questions to address concerns or roadblocks

23. What do you think about this so far?

As you go through your sales call, it is always good to check in with your prospect to see how they are feeling and what they are thinking. This is best asked after you do the talking for at least a minute or two.

24. What concerns do you have about making a change?

It is common for prospects to have unaddressed concerns about making internal changes in order to integrate your product or solution. Asking them about those concerns will help them air it out, build trust, deepen rapport, and give you insights on potential roadblocks to address before and during the implementation process.

25. What other areas would you like to discuss moving forward?

Even if you think you’ve covered everything, it is always good to check with your prospect to see if they feel the same way. With all the questions and answers prior to this point, they might not have had a chance to bring up other areas that they feel are also important.

26. How would you describe the level of service with your current provider? How are you evaluating different options/vendors?

This is a buying history question. Sometimes a prospect may not be happy with their current vendor and are looking for a new one. You will want to know what went wrong with the previous vendor, so your company doesn’t repeat the same mistakes!

Questions that help close the deal

27. What questions do you have that I haven’t answered yet?

Another open-ended variation of “do you have any questions for me?” that works really well closer to the end of the sales call. The real power behind this one is that it assumes that the prospect has questions that you haven’t answered yet. It’s effective at getting them to really dig deeper in their heads for more questions.

28. If you were to make this happen, what would it mean for you personally?

Much like #11 and #17, this is more of a visualization question. However, it’s especially powerful because it attaches their personal feelings and aspirations to the end result.

If your company were to make a proposal showing a roadmap on exactly how your solution would deliver those results for them, your prospect would be all over it because of what it would mean for them personally.

29. If you would overcome these challenges, what would it mean for your company’s bottom line?

This is similar to #28, except that it gleans insights as to how overcoming their challenges with your solution would affect their bottom-line revenue rather than your prospect’s personal feelings. Use this question if your prospects (and their bosses) are especially interested in the ROI of your solution.

30. What else can I do to help you finalize this decision?

When you’re close to a deal and it’s time to negotiate, ask them what you can do to help them with the decision making process. It might take a gentle persuasive nudge or two. The most important thing is that you understand what your prospect needs to finalize the deal, and that you use your own sales team and resources to make it work.

Bonus: Clarifying questions

You might already use these questions when talking with your colleagues without realizing it, but they are a great way to nudge the conversation forward and to make sure you’re not missing anything important.

31. What does that mean?

32. How does that work? Can you help me understand that a little better?

33. Can you tell me more about that?

34. Can you give me an example of this?

35. How did that affect you – personally, as a team and as a business?

What Not To Do: 5 Mistakes to Avoid While Asking Sales Questions

1. Don’t answer your own questions

Answering your own questions is the fastest way to turn off a prospect and cut off the flow of useful information. On the other hand, the more you let them talk freely, the more high quality information you can get from them.

Do this instead: Let them respond fully.

Once you ask a question, always give them enough time to respond fully and completely. No leading. No prompting. And most importantly, no interrupting.

Which brings us to the next point…

2. Don’t forget to listen to the prospect

Contrary to popular opinion, sales is not about pitching solutions from the outset. Sales is mostly about listening to your prospect. You’re here to gather information about your prospect and what they need. Ideally you should only do 20-30% of the talking on a sales call.

Do this instead: Talk less.

When your prospect is answering your question, listen carefully and take notes. Ask clarifying questions just like those above.

3. Don’t make it seem like an interrogation

Yes, we know. We gave you a ton of questions to ask. But you don’t have to ask them all rapid-fire like a cross-examination in a courtroom or police station. That won’t help build the necessary rapport to keep the conversation flowing.

Do this instead: Keep the conversation natural.

Pick out a couple of questions from each category on this list that fits the situation most naturally. Always listen to your prospect and keep the conversation natural.

4. Don’t jump straight into the solution

When a prospect talks about their problem, it is tempting to offer a solution straightaway. But doing so will likely turn off the prospect and erase any opportunity for you to gather more information and potentially valuable insights that help you understand the problem fully.

Do this instead: Be curious.

Think like a journalist. Explore their problem from all possible angles and prompt them to talk more so you can develop a better fitting solution for your prospects. Save your pitch for the end, or on a later call.

5. Don’t fake enthusiasm

Eager to prove themselves, novice sales reps sometimes “try too hard” and come off as overly enthusiastic — subconsciously or not. They might say “awesome!” or “that’s amazing!” and other exclamatory phrases like these. The problem is most B2B decision makers can smell this a mile away, and it’s not a good look.

Do this instead: Focus on listening to the prospect.

Act naturally, and don’t try to impress them. Offer genuine responses (1-2 sentence insights) to their answers.

Bonus tip: Be careful with the “Why” questions

One last thing. We want to remind you to keep “why” questions to a minimum and mind your tone of voice.

This is because “Why” questions sometimes sound a little too accusatory. Once every now and then is fine, but don’t ask them in quick succession lest it starts to sounds like an interrogation.

Do this instead: Use “How come” instead of “Why”.

It sounds more disarming and nonthreatening to most people.

Bottom Line: Let Your Buyer Speak

In fact, the ability to initiate and carry a meaningful dialogue with potential clients is so important that my consulting firm has begun keeping metrics on what we call “target talk time,” which represents the percentage of a sales meeting during which the target buyer speaks.

We’ve found that when the target talks for at least 30% of the meeting time, sales conversion rates improve dramatically.

Conversely, when target buyers talk less than 30% of the time, conversion rates suffer. That means that when you go into a meeting with a potential client, you need to be prepared to allow them to speak for at least a third of the time you’re meeting with them.

You need to facilitate this type of interactive discussion, and the best way to do this is to demonstrate that you have an insatiable curiosity to learn about your target’s professional mandates by asking them hyper-open-ended questions.

These types of conversations will ultimately set you up to close the sale by giving you a natural way to demonstrate your ability to address the very needs, desires, fears, or problems they described to you.

Their expressions of pain, uncertainty, and doubt, discovered in the meeting allow you to use your own buyer’s logic to justify a rational purchase rationale.

The more open ended sales questions you incorporate into your sales process, the more deals you will win!

Kraig Kleeman is the author, inventor, and originator of The Must-React System, the world’s leading sales development methodology. Kraig is founder & host of KraigKleemanTV, the world’s most 
powerful sales enablement and personal motivation YouTube Channel. Until proven differently, Kraig is the The World’s Greatest Cold Caller


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