24 Open-Ended Sales Questions Your Reps Should be Asking

employee raising hand with question
Jordan Scott
Jordan Scott
In Engagement, Sales, Trending
Jordan Scott is the Content Marketing Manager at Xactly. She attended The University of California at Santa Cruz, and received degrees in Literature and Education.

A critical sales skill is asking questions, right? There is just no way you can build rapport or adequately sell your product or service without getting beneath what is sitting on the surface. A proper needs analysis requires questions, and that goes for both in-person meetings and initial phone conversations. That’s a fact.

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 the open-ended sales question to be your bulldozer, uncovering the details that will help you stand out to prospective customers. To refresh your memory, these are the questions that cannot be easily answered with a “yes,” “no,” or other single-word synonym. Why should you be asking them? Because their composition encourages conversations to reach deeper levels (levels that will only increase the likelihood of you closing the deal).

While this is a straightforward sales technique, many reps simply get caught up in conversation. Then, either out of comfort or lack of experience, default to shallow, closed-ended questions that quickly end exchanges and thus limit the rep’s ability to discover if their product is a good fit for the prospect.

So if you need some guidance on the best open-ended sales questions you should be asking, how you should be asking them, and why it should be your top priority to do so, read on for 24 examples to use during your next call. Once done, you can find other ways to inspire sales performance, with tips from industry experts, in this guide.

List of Open-Ended Questions for Sales Reps

1. What will make this call worthwhile and successful for you? A good open-ended opening question that lets prospects know you are there for them—to listen to their needs rather than immediately throwing the typical sales pitch down on the table right out of the gates.
2. How do you manage your processes today? Why is that? Again, such a question allows your prospect to put their minds back into their day-to-day. Up to this point, they still might be in, “Oh great, another sales call” mode. So, put them at ease and let them surface potential bottlenecks or issues your product may be able to quench.
3. What is frustrating you with your current process? This could be a question asked instead of the previous, or, in addition to. If the latter, a better way to ask might be, “You mentioned frustration around XYZ. Can you elaborate?”
4. What’s working well with your current process? Rarely is every component of a process broken or need to be replaced. Thus, there might be certain aspects your prospect doesn’t want to lose with the implementation of a new solution. You should know that.
5. What factors are limiting your process from being as effective as it could be? Similarly, perhaps there are just a couple of things that need to be fixed with their current process. If you know this before your turn to speak, it will allow you to draw a stronger connection between your product features and the already-mentioned pain points.
6. In what ways would making this change disrupt your current processes? This is a trust-building question, in that it allows your prospect to see someone (you) who is confident enough to be asking for holes to be poked in their product. You, in turn, can now give a crafted rebuttal addressing why those might not actually be “holes” after all.
7. What is motivating you and your company to take on this project? One might typically ask this question like, “You said your company was struggling with XYZ, is that correct?” Even though problems may have been previously stated at some point, going the open-ended route will confirm the facts and could even give you more information with which to work.
8. How do you envision your challenges being solved? What does that solution look like? This question may be a bit risky if your prospect starts describing a facet your solution doesn’t provide. But, if you’ve made it to this point, your product should be a good enough fit for you to capably circumvent any potential issues. Also, if your prospect ends up describing your product features, you’re in an advantageous position.
9. What has been done to fix your issues so far? 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. If you have tried to solve the issue internally, what challenges have you run into? 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).
11. Why was this method tried instead of “X”? Again, just more discovery. It’s in your best interest to know why a certain solution was chosen previously. Why? Because how great would it be if your product was in alignment with what your prospect thought they were getting with another solution (that ultimately failed)?
12. How will you be evaluating different options? Which other vendors are you considering? 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.
13. 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. With so much being exchanged, sometimes it just takes your prospect seeing a benefit said alternatively, or on paper for the light bulb to illuminate.
14. 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 address anything that might help them move along towards getting a deal done.
15. If those steps include the signing of the final order too, what can I do to help that process along? Even with above question #14, your prospect might not be factoring in the actual closing action to get the deal in place. This follow-up question just cements all activities along that precious timeline.
16. 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. 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 surely get the prospect’s attention
17. If the problem you’re facing was solved immediately, what would that look like for your business? Think back to the times where you envisioned success for yourself; crossing that finish line in the distance…it motivates you to work that much harder, right? Similarly, this question puts your prospect in “superstar” mode, allowing them to get a quick glimpse into what it would mean for their career should they be able to solve “hot button” issues plaguing the company.
18. How do you think changing this process could make your job easier? And to go along with the “superstar” question above, getting prospects to visualize their jobs being easier with your product has a similar positive effect.
19. What are some of the specific things stopping you from reaching your objectives? Perhaps it’s budget, time constraints, or something else entirely. Whatever it is, you need to know it, and then feature it as a key piece when developing your perfect sales pitch.
20. 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.
21. Why do you think this challenge hasn’t been addressed yet? Really, this is a way to ask about potential roadblocks without being so blunt. Meaning, maybe one important person in the organization really likes the current process and solution, but most others want to make a change. Well, then you’ve just uncovered an issue that needs to be addressed sooner than later.
22. 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?”
23. 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.
24. 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.

Download our guide, “Inspiring Sales Rep Performance” for top tips from industry experts on how to inspire sales reps and maximize their selling power.

Examples help, right? To easily remember how to ask open-ended sales questions, just start with what, why, and how, and avoid jumping directly to “have you,” “are you,” “do you,” and “can you.”

If you’re asking open ended questions in your sales dealings, then you’re in a conversation that is helping you discover what’s needed from you and your product in order to close. To make your case even stronger, continue to probe for more information.

Five probing questions:

  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…?

…And five closed-ended sales 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:

Three loaded questions to avoid:

  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.

Updated with answers 2/21/16


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24 Open-Ended Sales Questions Your Reps Should be Asking

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