24 Open-Ended Sales Questions Your Reps Should be Asking

Jul 01, 2019
11 min read
Reps need to ask the right questions to succeed in sales organizations. These are 24 open-ended questions your team should be asking prospects to close deals.

Open-ended sales questions are a way for reps to open up a dialogue and gain a deeper understanding of prospects’ and customers’ needs more clearly. Typically, these questions cannot be answered with a simple “yes” or “no.” Rather, they require a more in-depth explanation, and ultimately, provide sales reps with key information to formulate a strong sales pitch.

A critical sales skill is asking the right open-ended sales questions. There is just no way you can build rapport or adequately sell your product or service without understanding a prospects pain points and current situation. Once you uncover that information, it becomes much easier to position your sales to focus on the benefits your organization provides the individual in their role.


Free Guide: Why a ‘One-Size-Fits-All’ Approach to Sales Compensation Planning Doesn’t Work


Why Ask Open-ended Sales Questions?

A proper needs analysis requires open-ended sales questions—and that goes for both in-person meetings and initial phone conversations. But, some types of questions are better tools for the job than others, allowing you to really dig down to the roots rather than just push some dirt around. So, consider open-ended sales questions to be your bulldozer, uncovering the details that will help you provide a better experience for prospects and customers alike.<div data-object="inline-CTA" data-objectname="Inline CTA" data-objecticonclass="mi-server" data-async="true" data-instanceid="C982CF31-42C8-4778-81683CFC211679EB" class="mura-async-object mura-object" data-objectid="387FA1D4-FE73-4256-AD260B5773059B61" data-inited="true" data-ctavariation="default" data-componentname="Complete Guide to Sales Team Compensation" style=""></div>

While this is a straightforward sales technique, many reps simply get caught up in conversation or get stuck focusing on relaying your product’s features. This can lead to prospect conversations that are full of shallow, closed-ended questions that quickly end exchanges and thus, limit the sales rep's ability to discover if their product is a good fit for the prospect.

To help guide your sales coaching and selling strategies, here are 24 open-ended sales questions your team should be asking. You can also jump ahead to different question types/sections with these quick links:

Initial Open-ended Discover Questions
Open-ended Questions to Uncover More Background
Open-ended Questions to Eliminate Doubts & Concerns
Open-ended Questions to Close the Deal
Probing Sales Questions to Get More Information
Closed-end Sales Questions to Avoid

Initial Open-Ended Discovery Questions (to Get to Know Prospects)

1. What will make this call worthwhile and successful for you?

A good initial open-ended sales question establishes that the conversation is meant to focus on the prospect’s needs from the start. Questions should set sales reps up to listen to prospect needs rather than immediately throwing out the typical product feature sales pitch down on the table right out of the gates.

2. How do you manage your processes today? Why?

Again, this type of open-ended sales question allows your prospect to focus on their day-to-day operations. Up to this point, they still might be in, “Oh great, another sales call” mode. This question helps put them at ease and lets them surface potential bottlenecks or issues your product may be able to solve.

3. What is the biggest challenge/frustration you face with your current process?

This is a good question to open up the floor to dive deeper into the prospect’s pain points. You could also frame a follow up to this question to focus on a specific challenge mentioned in the prospect’s answer, such as “You mentioned frustration around XYZ. Can you elaborate?” 

4. What’s working well with your current process?

It is very rare that every component of a process is broken or needs to be replaced. More often, there are parts that can be changed to improve the overall process. However, there might be certain aspects the prospect doesn’t want to lose with the implementation of a new solution. 

In some cases, a prospect might be thoroughly happy with their process and not realize there are still improvements that can be made even if they are happy with their current operations. You should know that and frame the conversation to show how your product can enhance those aspects.

5. What factors are limiting your process from being as effective as it could be?

Sometimes prospects feel their current operations are already running smoothly. If the answer is that there aren’t any real challenges or limitations, a good followup question would be “What is one thing you wish you could improve in your processes—whether it be efficiency, timeliness, accuracy, etc?”

6. What are some of the specific things stopping you from reaching your objectives?

Perhaps it’s budget, time constraints, or something else entirely. Regardless, this is important information to consider in your sales approach. From the start, sales reps should have a clear understanding of potential roadblocks and issues the prospect is facing. 

7. Other clients we’ve spoken with are challenged by common issues like ‘A, B, and C.’ How are these challenges affecting your business?

This type of statement/question combo can accomplish a couple of things. For one, it shows you’ve done your homework, and even if you haven’t spoken with anyone challenged with those things, it allows you to surface other common problem areas your product might address. Secondly, if you have another customer in a similar industry or even a prospect’s competitor, such a question will help establish credibility with the prospect.

Open-ended Sales Questions to Get More Background

8. What is motivating you and your company to take on this project?

This question helps reinforce the central pain points a prospect is facing and shows reps what they see as their main priority. It also provides the opportunity for prospects to add in additional details—and the more information your reps can gather, the better. 

9. What has been done to fix your issues so far?

This helps understand what hasn’t worked for the prospect in the past so that reps can dispel concerns of these failures happening again later in the sales cycle. Additionally, this is a great question that, if answered favorably, will lay out on a silver platter all the reasons your solution is superior to other available options.

10. What worked best with your previous solutions?

Again, just more discovery. It’s in your best interest to know why a certain solution was chosen previously. Like current processes, previous attempts at solving challenges internally might not have all been bad. It’s important to understand what has worked in the past and find a way to tie in your products and services to align with that.

11. What challenges have you run into with other solutions you’ve tried?

Similar to the above, perhaps your prospect has already tried to fix their problems with internal band-aids and just needs something bigger and better. You can expect greater buy-in if it is your prospect doing the talking about their problems, with you following-up with statements about the solution (rather than you doing all the talking).

12. How would changing this process could make your job easier?

This question helps reps start understanding what prospects prioritize in their role. With that in mind, you can craft messaging to show how your product can make that vision a reality for that individual.

13. If the problem you’re facing was solved immediately, what would that look like for your business?

This takes the previous question further to include more than the individual. On their end, prospects will have to convince their managers and VPs of the need for the product. This helps them do that by showing the value it provides for the individual, their team, and the entire organization as a whole. 

14. What does your ideal process/situation look like? What would you be able to achieve?

While this question may be a bit risky if your prospect starts describing a facet your solution doesn’t provide, it gives you a clear picture of what they want out of a solution. Again, this provides more information for reps to personalize the conversation and focus on the prospect’s needs. 

It can give you an opportunity to tie in additional features that might be more of a “want” rather than an immediate “need” or even open the door to adding on additional products to the deal.

Open-ended Sales Questions to Eliminate Doubt & Concerns  

15. In what ways would making a change disrupt your current processes?

This is a trust-building question—it allows your prospect to share their concerns in changing their current process to adopt your product or service. It also helps reps turn the conversation to the benefits the prospect will see in addition to solving their current pain points.

16. What are your concerns about making a change?

This question puts resources aside, and really encourages the prospect to lay their cards out on the table. Sure, nobody has enough budget or time, but what is it that really concerns your prospect about making a change? You’d be surprised at what you might learn here. It could be something as small as your prospect being fearful of proposing a change to higher-ups.

17. How are you evaluating different options? What other vendors have you considered?

You should obviously have a good idea of your competition, and who your prospect might be considering in addition to your solution. But, if you know specifically (by hearing it directly from the prospect), you can narrow your focus and attack with depth rather than breadth. This gives you a chance to focus on your company’s differentiators—both for your product and overall company—and show what makes you the better choice.

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

Trick question. Asking this doesn’t really encourage additional dialogue, and can really stop any momentum previously built. So, a better approach could involve you being more transparent with pricing, stating something like, “The average spend for others in your position is $XYZ. Can you talk me through how this aligns with your expectations?”

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

A perfect way to end, as you can bet anyone serious about finding a solution will have more specific questions to ask of you. If they don’t have any questions, consider it a sign that you need to be doing more to connect their problems to your solution.

Open-ended Sales Questions to Close the Deal

20. How will the decision-making process work?

A mistake some sales reps might make is to ask, “when can I expect to hear from you.” Why? Because how much can you do with an answer like “in a couple of days”? There isn’t any value there. On the other hand, if you hear everything that needs to happen next, you can keep the deal rolling along smoothly and address anything that might help them move towards closing the deal more quickly.

21. Who else should we involve in this conversation? 

This opens the door for prospects to bring in the true decision makers—normally a VP or C-level executive who needs to understand the true business value you provide. A good follow up to ask is “What concerns do you see your team having when it comes to making this change?” This will help you prepare for future conversation with additional stakeholders and can help shape any specific demo scenarios you might need to close the deal. 

22. What things might get in the way of this moving forward?

This might sound like the above, but the goal of asking differs slightly. For instance, while budget might be the long-term roadblock, there could be a shorter-term hurdle that must be cleared first. Perhaps you’re talking to someone who doesn’t have the authority to make the purchase, and convincing that decision maker is the immediate challenge.

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

This is a good question given our struggle to retain large chunks of information presented during a short amount of time. This is the perfect time to use your sales-marketing relationship wisely and use specific content (guides, case studies, infographics, etc.) to provide key details in an easy-to-read format for prospects to share internally with their team.

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

This is where negotiating comes in. In any deal, the goal is close—and sometimes it takes a little additional persuasion. You should understand what terms prospect needs and utilize your own internal sales resources and team to make the deal work.

Examples help, right? To easily remember how to ask open-ended sales questions, focus on discovering the what, why, and how. If you’re asking open-ended questions in your sales meetings, then you’re in a conversation that is focused on the prospect and aimed at helping you discover the benefits you can provide. 

To help further strengthen sales team training and success, here are some additional probing questions and some to avoid completely.

Probing Questions to Get More Information

In many cases, prospects will provide an answer that doesn’t give all the information you need and requires a follow-up. Use these questions to continue the conversation:

  1. What did you mean when you said “X?”
  2. Oh, how so?
  3. What does this all mean to you, personally?
  4. Why is that?
  5. Can you clarify for me what you meant by…?
  6. Can you elaborate on XYZ?

Closed-end Sales Questions to Avoid

There are also questions that can halt or derail a sales conversation, and in the worst case scenario, result in a lost deal. These are questions to avoid:

  1. Have you heard of us?
  2. Are you happy with how you manage that?
  3. Do you have a formal decision-making process?
  4. Is that the most important thing to you?
  5. Can you convince your boss?

It’s also good to avoid loaded sales questions, which include an assumption in the question and can leave your prospect feeling a bit manipulated or pushed into an answer they’re not comfortable with. You want to treat your prospects like people after all. Note that these examples are closed-ended questions as well as loaded questions:

  1. Are you comfortable losing money each month?
  2. Is your goal to be a follower in the market?
  3. How much are you off on your forecasts?

A string of yes or no questions can also end up feeling like an interrogation and not a useful conversation. To avoid that, use probing sales questions. What you want to do is ask questions that require the answer to be an explanation based on the prospect’s knowledge and insight.

However, good open-ended questions should also be objective and not lead the prospect to an answer. 

They also make it easy to ask follow-up questions, which is what makes a good conversation. So, when you’re qualifying and discovering details with a prospect, use open-ended questions to engage in a useful conversation that gets you the details you need.

An added bonus is that from the prospect’s point of view, they’ll feel that they’re having a conversation with someone who understands them, as opposed to being drilled with a bunch of yes/no questions. Finally, after you ask a question, listen to the answer instead of just waiting to ask the next question. 

Want to strengthen your sales coaching further? Download our “Complete Sales Planning Handbook” to set your sales team up for success.

  • Sales Coaching and Motivation
Jordan Scott
Jordan Scott
Manager, Content Marketing

Jordan Scott is the Manager of Content Marketing at Xactly. She attended The University of California at Santa Cruz, and received degrees in Literature and Education.