40 Open-Ended Sales Questions + How to Ask Them

Everybody’s telling you to ask questions, ask questions, ask questions.

But are you asking the right questions?

If your prospects are giving you single-word answers—mainly yes or no—and you feel like you’re always lacking important information about their situation and the deal progress, then you’re probably asking the wrong questions at the wrong time.

Open-ended sales questions are built to get your prospects talking, and can also help you control the direction of the conversation.

Let’s break down:

• What are open-ended sales questions, and why should you use them?
• When and how to ask open-ended questions in sales
• 12 open-ended questions to genuinely understand the prospect’s situation
• 11 questions that help you dig beyond the surface of an initial answer
• 4 open-ended sales questions to prove you’re an expert they can trust
• 5 questions that establish the impact of current problems and the value of your solution
• 8 open-ended questions you can use to build a clear path to purchase

What are Open-Ended Sales Questions and Why Should You Use Them?

Open-ended sales questions cannot be answered with Yes or No. They inherently require the other person to talk more freely. Using open-ended questions allows your potential customers to open up, giving you key insights to qualify and move the deal forward.

In general, these are questions that will start with what, how, when, where, who, or why. These questions make the prospect think and give an answer that can be more useful to you as a salesperson.

What’s the purpose of asking these questions?

First, open-ended questions give your prospects space to talk. The longer their answers, the more information you can gather, including pain points, qualification factors, or potential deal-stoppers.

Research from Gong found that longer customer stories correlated directly with higher success rates.

Second, the right open-ended questions help you build trust and establish authority. After all, any salesperson can read questions off a list—only a true expert can naturally include questions in a conversation that directly relate to what the prospect just said.

Note: Be very mindful and intentional when asking why-questions. Never use why questions that require a prospect to justify their actions or choices—this will put them on the defensive. Instead, use why questions to get more context and a better understanding of your prospect's priorities.

When and How to Ask Open-Ended Questions in Sales

The main situations where you want to ask open-ended sales questions would include:

• To genuinely understand the prospect’s situation
• To dig beyond the surface of an initial answer
• To prove you’re an expert they can trust
• To establish the impact of current problems and the value of your solution
• To build a clear path to purchase

How do you make sure your questions are well-received? Approach the conversation from a perspective of genuine curiosity. Integrate these questions naturally into the conversation, and then listen attentively.

As James Urie, Sr. Account Executive at Close puts it: “Don't feel like it has to be rapid-fire, one question to the next. Allow them to compound and build and complement each other. Pause and think about things as an expert so that you can provide the most value.”

The best way to ask open-ended sales questions is to use the inverted pyramid method. Ask broad questions first, and then use open-ended questions that are more specific to the responses you receive.

When done correctly, this will help you build a more natural conversation with prospects.

Let’s dive into each of the situations we discussed above, and give you specific examples of open-ended questions you can use to accomplish those goals.

12 Open-Ended Questions to Genuinely Understand the Prospect’s Situation

A good consultative seller will spend time getting to know their prospect (and no, that does not mean building phony rapport).

Instead of pretending to be interested in the weather wherever they are, be genuinely curious about their job, their business, and the challenges they’re looking to overcome.

Let them know you have their back by asking questions that help you understand their situation:

1. Catch me up, give me some context on what you’re trying to do

James Urie uses this question to start his discovery calls. Here’s how he explains it:

“I want to keep it super open-ended at the front. I just want to get them talking. So, my initial sales question is going to be: ‘Catch me up. Give me some context on what you’re trying to do.’ They can’t say yes or no to that question. It requires thought. They’re going to give you some level of detail. That’s either going to give you the whole picture, or it’s going to lead to another question.”

2. Why did you take this call?

This is a great question for both inbound and outbound sales processes.

The point: get to know the main trigger that led to your current conversation.

Understanding the catalyst that led them to fill out a form or respond to your cold email will tell you:

• The main issue they’re trying to solve
• The urgency of the problem

3. What’s missing in your current process/tech stack?

Process and productivity are two of the main customer pain points that your prospects could be facing. With this question, you can discover what they’re lacking, what they’re looking for, and whether your solution fits the gap in their process or stack.

4. Is this the first time you’re considering a product like this?

Okay, I know, this isn’t technically an open-ended question. But this question opens the conversation to see what other options this prospect has tried, and what their process has been for discovering new solutions.

If they say no, you can follow up with:

• Which other products did you consider?
• Who else was involved in adding those products to your list of options?
• How did you come to decide those weren’t the best options for your team?

If they say yes, you might ask:

• What was stopping you from looking into this before?
• Why now? What’s changed that made this more of a priority?

5. Tell me some specific obstacles that are threatening your goals for this quarter.

You’re not here to advise them on their business goals and numbers. So instead of getting hung up on company initiatives and team goals, talk about what’s blocking progress and making it difficult to reach those goals.

When you understand the obstacles, you can better help them look for workable solutions with your product.

6. In an ideal world, what does this process look like for your team?

When people think within the constricts of ‘the budget’ or their individual authority, it can be harder to imagine what they really want.

Use this question to help your prospect think outside the box. See what they actually want, and then you can help them discover solutions or workflows that they may not have considered.

7. What other options are you looking at right now?

This is a standard open-ended sales question example for a reason. It’s unlikely your prospect is ONLY looking at your product. If they’re serious about finding a solution, they probably have a list of options they’re considering.

So, find out what they’re looking at. Then, ask good follow-up questions to see what they like or dislike about these options.

8. Who is going to benefit most from a change in this area?

This question accomplishes two goals:

• Start to establish the value of change
• Help you understand who is involved in this decision

You want to discover decision-makers as early as possible since they’re an essential piece of closing the deal. But this question helps you uncover another group that is key to retaining this customer down the road: the end-users.

Understanding who will see the most benefit from a change is part of a holistic sales approach, meaning you’ll get access earlier to this group of users and win them over as internal champions for your product.

9. Which KPIs are you measuring to track success for your team? How do you measure those KPIs?

While you know that success with your product means more than just metrics, key decision-makers need to understand the numbers behind a change.

When you know the main KPIs this team uses to measure success, you can help build a case for your product that revolves around those key metrics. This is vital information for your sales pitch, especially when decision-makers join the deal.

10. What is your manager/CEO expecting you to accomplish in the next quarter/6 months/year? What are some hurdles you need to overcome before then?

Understanding the expectations of higher-ups puts you in a better position to stand up for and help your prospect. Remember, sales isn’t just about closing the deal: it’s about making your prospect’s life better.

So, learn about what they’re expected to do, and help them overcome those hurdles. This makes you the friendly advisor who’s got their back individually, making you a powerful ally they trust, continue to buy from, and refer to peers.

11. What are your top priorities when using a tool like ours?

This is an especially important question for prospects that have used similar tools in the past. What metrics were they expected to report on? How was success measured? If they stopped using a similar tool in the past, what caused them to change?

Understanding these priorities helps you build an effective sales pitch down the road.

12. How do you see your business growing over the next year? How would your needs change in this area?

Know the roadmap for your prospects’ business, and you can set yourself up as a long-term partner, not just a temporary software solution.

This open-ended sales question gives you the insights you need to set this prospect up with the right plan and make recommendations that will help them down the road, not just today.

11 Questions That Help You Dig Beyond the Surface of an Initial Answer

You’ve started to scratch the surface—now it’s time to get the shovel out and start digging.

Here are 11 open-ended question examples for sales reps who want to give their prospects the best chances for success.

13. What do you like/dislike about [current solution]?

What are your prospects currently using to make things happen? Sure, they’re interested in a new solution—but there are probably still some things that they like about what they’re currently using.

Finding out what’s an issue and what’s not within their current workflow or tech stack will help you give more effective product demos.

14. What’s the #1 issue on your priority list for this quarter?

What’s the top priority for this team? If it’s not something that involves your product, that’ll tell you where you sit on their to-do list.

15. You mentioned [challenge] is an issue right now. Can you explain where specifically you’re seeing that impact?

An open-ended question like this allows your prospects to talk freely about the challenges they’re facing.

Asking about ‘impact’ and letting the prospect interpret that on their own will tell you a lot about their priorities. Their answer could be a monetary impact, an impact on a key metric, or the emotional impact on their team.

16. What have you tried in the past to overcome this issue? Why didn’t that pan out?

Learning about past experiences and tests will tell you what works and what doesn’t for this team. You can also give better recommendations when you know what they’ve tried already.

17. What’s something you wouldn’t want to change about your current workflow/tool stack?

With this question, you’ll learn what’s sticking around in the long term. Does their ideal tech stack work well alongside your product? Is there a piece of their preferred workflow that’s made easier inside the solution you’re offering? (If you're interested in sales tools, check out Building the ultimate sales stack: 3o tools you should know.)

18. Do you have a plan B for this issue?

Almost everyone has a plan B, whether it’s to build a solution in-house, stick with the current stack, or go with a different solution.

When you understand what the plan B is for this team, you can better advise them on how to move forward, or give them the right information to show which direction is best for their team.

19. Can you give me an example of that?

Dealing with a tight-lipped prospect? Use this open-ended sales question to get them to expand on the details

Here’s how it might look in a conversation:

Sales rep: “So what’s the main challenge you’re looking to solve?”

Prospect: “We need something that helps us be more productive, our team isn’t working efficiently.”

Sales rep: “Ah, I see. Can you give me an example of where your team lacks efficiency?”

Prospect: “Well, they don’t have a clear direction on where to start when they log on in the morning. They’re losing important information and urgent tasks in email threads.”

Now, instead of a general challenge in ‘productivity’, you have a clearer view of where your prospect’s team needs help.

20. Tell me more about…

While not technically a question, this open-ended statement gives the prospect freedom to speak at length. If you need more detail about a specific piece of their process or challenge, this is a great way to start that ask.

21. What led up to this issue? Why is it such a problem now?

Get some backstory on the problem. This context will help you see what changed, what direction the team is going in, and where your solution fits into their current situation and future expectations.

22. Was budget a barrier to solving this problem before?

This question starts to dig into the question of budget without asking straight-out how much money they’re willing to spend. Their answer will probably give you context on where they’ve seen pushback on big spends in the past, as well as who needs to sign off on a purchase—vital information for when you’re ready to close the deal.

23. What kind of support would your team need to become insanely successful?

Support is another one of the four most common customer pain points. Do they need professional services to manage the software solution? Do they need someone to help them clean up or migrate data? Does the team need training on the software?

4 Open-Ended Sales Questions to Prove You’re an Expert They Can Trust

A truly consultative salesperson is an expert in their field. But you can’t just tell someone that you’re an expert—you need to prove it.

These 4 open-ended question examples are the kind of questions only an expert can ask and will help you establish authority in the sales process:

24. Walk me through your process for…

This question makes it clear you want a long answer, but also allows you to get specific.

For example, instead of:

“Walk me through the first steps of your sales process.”

You could say:

“Walk me through your process for qualifying new leads and matching them to your ICP.”

Only someone who knows sales could ask that question. You can do the same: prove with your questions that you know your customers’ industry and unique situation.

25. Have you ever tried…

Here’s another example where you can get specific.

For example: “Have you ever tried using lead generation forms on your website as an early qualifying process?”

26. What’s your team’s take on…

Finish this sentence with a recent industry change, a new tech announcement, or something else current in the industry.

When you shape this question to be relevant to the solution you’re offering, you’ll also get some context on their feelings toward what you’re selling.

For example:

• “What’s your team’s take on the whole ‘cold calling is dead’ trend?”
• “What’s your team’s take on the BANT qualification method?”
• “What’s your team’s take on selling over Zoom?”

27. Which tools are you using for…

In-depth tech stack questions are always great to prove expertise in a certain field.

For example:

• “Which tools are you using for lead generation?”
• “Which tools are you using to help you qualify those new leads? Are you using a B2B data provider to qualify before setting up a call?”

5 Questions That Establish the Impact of Current Problems and the Value of Your Solution

You can tell your prospect that your solution will save them time and money or help them reach their goals. But when you ask the right questions, you can help them reach those conclusions on their own.

Here are some open-ended question examples to prove value:

28. What’s the current toll on [main metric]?

You’ve already discussed the problem, the obstacles to a solution, and the key KPIs that your prospect is tracking.

So, this question wraps that all together to show the measurable impact of this problem.

29. If this isn’t solved in the next [6 months/quarter/year], how will that affect [main metric]?

This open-ended sales question takes the prospect into the future. If they’re caught up in the day-to-day grind, they may not have considered the long-term impact of this problem. Either way, this question will definitely get them thinking.

30. If you don’t find a solution today, where do you see your team in 6 months?

This question is similar to the last but has a clear push for genuine urgency.

Here’s how it might sound in a conversation:

Sales rep: “You mentioned that your team’s close rate has decreased by 15% because of problems with your lead generation system. If this doesn’t get solved today, where do you see your team’s close rate in 6 months?”

31. If this was solved today, what would be the impact on your team? On your business?

Now, flip it around. Focus on the positive impact of finding the right solution with these open-ended questions.

For example: “If you could clean up your lead generation process today, what would that do for your team?” Asking these questions is a powerful way to create urgency in sales that drives the prospect towards a decision.

32. What would an x% improvement in your [KPI] mean for the team?

You know which KPIs mean the most to your prospects, and you know what the possibilities are based on what current customers are seeing.

In a conversation, this question might look like this:

“I know productivity is a huge issue for your team. If you could boost their productivity by 35%, what would that mean for you?”

8 Open-Ended Questions You Can Use to Build a Clear Path to Purchase

Questions aren’t just for discovery or qualifying. Through the buying process, you want to continue using questions to keep your prospects talking and get a clear view of their buying process.

Here are 8 open-ended questions for sales reps prepping to close the deal.

33. How does your team view this issue? How does upper management feel about this issue?

Aside from your POC, the two most important groups you need to win over are the end-users and the decision-makers.

This question allows you to take the temperature on both of these essential groups.

34. When was the last time you made a purchase like this? Walk me through that process.

Purchase processes differ from company to company. Instead of asking for the typical procedure, this question narrows in on a recent purchase to see how things are really done on a day-to-day basis.

35. Ideally, when do you want this to be implemented? Do you think that’s a reasonable timeline?

Timelines can be tricky. Maybe your prospect would love to be onboarding their team in the new software by next week, but won’t get purchase approval until next month.

Asking about the ideal timeline vs. a realistic timeline may help you uncover obstacles that will slow down this purchase (and help you prepare for them beforehand).

36. Who has the final say on purchases like this? How do you plan on pitching this to them?

Your POC will probably need to get approval from someone else on the team. As an internal champion, they’re not as adept at pitching your product as you are. Learn about their plan for the pitch, and you’ll see ways you can help them specifically to pitch your product internally.

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

This is a great question to ask as an alternative to: “Do you have any questions?”

38. Who else should be invited to our next meeting?

Get stakeholders involved early on. Preempt objections from higher-ups down the road by building them into the process before.

39. What kinds of content or collateral can I send you to make this process easier?

When you start to see the outline of this prospect’s purchase process, you may notice areas you can provide helpful content that will speed up the deal.

For example, do they need to do a presentation to pitch your product to higher-ups? Send them the information they need to make a business case. Offer them sales pitch templates they can use internally. Does their legal department need to approve contracts before they’re signed? Get those contracts over earlier so they’re already approved when your prospect is ready to sign the deal.

40. What will it take for you to become a customer?

This question takes your prospect through the virtual close. Keep asking follow-up questions until you’ve built out a clear path from where you are now to close the deal.

Ask the Right Questions to Get the Right Answers

The key to asking the right questions is to think about the answers you want to get.

You won’t be asking all 40 of these questions on your next qualifying call. But you can choose the right questions by:

• Taking the time to do research into your prospects’ companies
• Understanding where they are in the buyer journey and asking your questions accordingly
• Knowing the outcomes you want from this call

By doing this, you’ll ask the right questions, receive the right answers, and get one step closer to closing the deal.

Want to level up your sales game even more? Download our list of the most powerful B2B sales questions.