The Power of Open-Ended Sales Questions (With 12 Killer Examples)

10 min readJuly 22, 2020

Bestselling author Chris Voss has negotiated some of the most difficult deals in history. As a lead negotiator for the FBI, he found himself in more than a few life-and-death situations. From his career in the FBI to his transition to being a business consultant, Voss consistently used a tactic to gain a powerful edge in negotiations: asking open-ended questions.

When receiving a ransom demand, for example, Voss might ask “Now how am I supposed to do that?” Notice that this isn’t a question that can be answered with a simple “yes” or “no.” And by asking the question, Voss was able to get his negotiation counterpart talking in order to learn more about what they really wanted. And guess what: that same tactic is powerful in any sales scenario. No matter what you’re selling, asking the right open-ended questions can not only make your prospects feel like you’re listening to them, it can allow them to reveal information that may be vital to your closing the deal.

Open-ended questions are powerful because they get prospects talking. And our research has shown that the most successful reps do a heck of a lot more listening than talking (in fact, all-star reps rarely talk for more than 12 seconds at a time). And in this post, I’m going to detail some of the most powerful open ended sales questions that you can ask your prospects. I’ll also detail why each question is important and give some tips on what you should be listening for in your prospects’ answers.

Open-Ended Questions vs. Closed-Ended Questions

Whenever possible, try to replace closed-ended (ones that can be answered with a single word answer) with questions open-ended questions that take more than one or two words to answer. The best way to do this is by thinking about the word you’re using to start your question. Questions that start with “is” or “would” can easily be answered with a yes or no. And questions that start with the word “when” can often be answered in a word or two.

Think about it, if your friend asked you “would you like to go to the beach this Saturday” you would probably either answer yes or no. But if your friend asked you, “what would you like to do this Saturday?” It would probably require a longer answer. That’s because questions that begin with the word “what” are open-ended questions.

Here are some words that closed-ended questions start with, versus those that open-ended questions begin with.

Closed-Ended Questions

Start with: is, are, do, did, have, was, would, which, who, when, where

Open-Ended Questions

Start with: Why, what, how

So when possible practice replacing those closed-ended questions with questions that begin with “what”, “how” or “why.”

Example:

Replace “Do you have a budget set aside for this solution?” with “How would you go about getting a budget approved for this solution?”

Open-Ended Sales Questions Examples

If you’re looking to close more deals this quarter, here are some of the best open-ended questions you can ask to drive more revenue.

Questions to Communicate Value

Simply put, until your prospect truly understands the value of your solution, you’re never going to win a deal. Factors like budget and timeline are meaningless when a prospect doesn’t see the value of your solution. Here are some open-ended sales questions that can help you get your prospect to understand your solution’s value.

What are some ways that could make your life easier?

Why it’s powerful: This is a great question to ask after a demo. It gets your prospect to imagine their life with your solution and how it can be better. Best of all, it allows your prospect to do the selling for you.

What to look out for: If your prospect doesn’t do a good job of communicating your solution’s value proposition, it means that you have your work cut out for you. Drill down further, relate how certain customers are using various features to gain X,Y and Z benefits, and ask if those benefits would be valuable to them as well.

What results would make an investment in worth it for you?

Why it’s powerful: This is really a question about ROI. And by asking this question, you can find out what kind of ROI they’re looking for in order to invest in your solution.

What to look out for: If they don’t have a clear answer to this question (which is very possible) it opens an opportunity to have a frank discussion about ROI. When possible, have an ROI calculator ready to help show them how much they could potentially gain from investing in your solution as well as when they should expect to see those results.

What would your ideal solution look like?

Why it’s powerful: Asking a prospect to describe their ideal solution gives tons of insight into which features of your solution they’re going to think are most important. It can also help you identify whether there are any feature gaps that need to be addressed.

What to look out for: Your prospect might really think they need a feature that your solution doesn’t offer. This happens all the time. But the question is: do they really need that feature. If a prospect’s ideal solution includes a feature you don’t offer, don’t be afraid to ask why they think they need it. You might be able to uncover a better way to solve their problem than the way they’ve imagined solving it.

What are your main concerns about ?

Why it’s powerful: Have you ever been on a sales call where the prospect seemed like they liked everything about your solution, and so you think the deal is as good as closed, only to have the deal go cold? Often prospects have concerns about your solution that they aren’t going to proactively voice. And trust me, it’s always better to know what these concerns are. If you proactively ask what their concerns are, you can work with them to overcome those objections.

What to look out for: Are there concerns valid? Sometimes your solution is just not going to be the right one for a prospect. When this is the case, it’s good to waste as little time as possible. But the truth is, even objections that seem insurmountable can be overcome. As an example, a prospect might think that your solution isn’t the right one because it’s missing a certain feature. But maybe that feature could be easily built for them in one dev sprint. Or maybe the feature isn’t as important as they think it is.

Questions to Uncover the Buying Process

B2B buying cycles now require 6-10 decision makers on average according to Gartner. So one of the most important tasks for a B2B salesperson is to figure out what a company’s buying process is. This includes not only identifying who key stakeholders are, but also how each one might influence a deal.

What’s your process for getting budget approval for new solutions?

Why it’s powerful: This is one of my favorite open-ended sales questions. Instead of just asking if they can pay for your solution, it asks them a general question about how they get budget approval for any new solutions. Don’t be surprised if your prospect divulges a ton of useful information that can help you identify:

  • The prospect’s authority
  • Key stakeholders
  • Buying process
  • Whether there is budget set aside

What to look out for: If you ask them this question and they immediately go to an objection like “we don’t have budget” it simply means that you need to do a way better job of selling your solution’s value. In fact, I don’t recommend even asking this question until you feel like you have adequately communicated the value of your offering.

Which members of your team might also benefit from the solution?

Why it’s powerful: This question allows your prospect to identify other key stakeholders who should be brought into the buying process sooner rather than later.

What to look out for: You might hear something unexpected. As an example, your prospect might see value in a solution for another department in their organization that wasn’t even on their radar. As an example, let’s say you’re selling chatbot software.

You may have started out by targeting the marketing department. But if you ask which team members can benefit from the solution, the prospect could let you know that their customer success team could really benefit from the solution as well. You could therefore bring customer success into your buying process. And by the way, when multiple departments use a solution it tends to be much easier to get budget.

What other solutions are you looking at?

Why it’s powerful: B2B buyers are more educated than ever, and chances are that if they are actively looking at your solution, they’ve researched the competition. But which competitors are they looking at? Knowing whether A) a deal is competitive and B) who the competitors are, helps you position your solution, explaining why it’s a better fit than the competitors they’re looking at.

What to look out for: If a prospect mentions a competitor you can speak until you’re blue in the face about all the reasons why you’re better than that competitor. But if you have a case study or testimonial prepared in which a customer can say, in their own words, why they chose you over that competitor it’s going to be way more powerful.

Is there any information I can send you to help make your decision easier?

Why it’s powerful: It’s common for salespeople to send collateral following a meeting. But it’s vital to ensure that the collateral you’re sending is actually something that might help them make a decision. Some of the most helpful collateral to send post-meeting tends to be pricing sheets, ROI calculations, case studies and short solution briefs that clearly outline the value—key for getting stakeholders quickly onboard.

What to look out for: As a general rule, assume that every single piece of collateral you send could end up in the hands of a competitor. In a competitive deal, prospects sometimes share collateral with competitors to see how they stack up. So be careful to avoid putting sensitive details in writing that you wouldn’t want a competitor to see (e.g. product roadmap).

What do you think the best next steps would be?

Why it’s powerful: This is a good question to ask toward the end of a call. It can shed light on what they think the next part of the buying process is, who should be brought in and when (or if) the next call should take place.

What to look out for: If your prospect is unsure of next steps it can be a warning signal that either value hasn’t been properly communicated or else they are unsure of what the best buying process should be. Or maybe it means they don’t have the authority to decide how to proceed. If that’s the case, it’s important to discover who the next best stakeholders are in the organization is and try to broker a meeting with them.

Questions to Influence Timeline

Timeline is important in B2B sales, but often you can help influence that timeline by communicating value and getting underneath their buying process as it relates to implementation timeline.

What are some problems that could help you solve immediately?

Why it’s powerful: This question could easily have gone under the value section, but the word immediately is key. By getting prospects to think about immediate benefits it can have a powerful influence on timeline discussions to follow.

What to look out for: If your prospect can’t envision quick value from your solution, they might need some help from you. Ask follow-up closed ended questions like, “what if we could help you do this month, would that be helpful?”

What could be the cost if you don’t implement this year?

Why it’s powerful: Just like you want prospects to imagine the better world that awaits them from implementing your solution, you also want to make sure they see the cost of not implementing that solution in a timely manner. By allowing them to focus on the pitfalls of not implementing a solution, it can sometimes expedite a decision.

What to look out for: They might not know the answer to this question. If that’s the case it’s another great opportunity to bust out the ROI calculator and help them quantify the cost of not implementing your solution.

In a Perfect World, When Would You Ideally Like to be Up and Running?

Why it’s powerful: This is a pretty standard sales question. But it’s important to phrase it as an open ended question. Because you might uncover some interesting information related to their implementation timeline.

What to look out for: Prospects will often volunteer information about their implementation timeline. For example, they might mention that they are currently under contract with a competitor for the next three months.

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About the Author

Jesse WestDirector of Lifecycle MarketingringDNA

Jesse Davis West is Director of Lifecycle Marketing at ringDNA, focusing on improving the experience and maximizing the lifetime value for customers across their entire journey. Drawing on 9 years of B2B marketing experience, Jesse is passionate about communication, branding and strategic marketing. He also plays a mean lead guitar and can throw down at karaoke.