20 Open-Ended Sales Questions Your Reps Should be Asking

Aug 19, 2021
9 min read
You need to ask the right questions to build strong relationships and close sales deals. These are 20 open-ended questions your team should be asking prospects to move deals through the pipeline and close.

​In sales, your conversations and interactions with prospects can make or break a deal. Open-ended sales questions are a way for you to start 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 key information to indicate the best solution for the prospect.

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

The Four Levels of 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 it’s important to focus on questions that allow you to really get to know the person or organization on the other side of the phone. 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>


There are four levels of open-ended sales questions to help you gather information throughout the sales process. At each level, you start to dig deeper into your prospect’s challenges, operations, and goals.

  1. Level One: Getting to Know Prospects
  2. Level Two: Gathering More Background Information
  3. Level Three: Eliminating Doubts and Concerns
  4. Level Four: Closing the Deal

To help guide your sales coaching and selling, here are 20 open-ended sales questions your team should be asking. 

Level One: Getting to Know Prospects

During the discovery phase, it’s important to set a foundation for the rest of the sales process. You need to identify how your prospect is operating right now and what their frustrations are. This will help you craft a personalized solution that specifically addresses their unique needs.


1. How are you currently managing your day-to-day processes?

This sales question allows your prospect to focus on their day-to-day operations. At this point in the relationship, they still may be hesitant to talk with a sales rep. This puts them at ease by placing the focus on their situation and opens the door for them to surface potential bottlenecks or issues your company can solve.

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

It’s 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. You should know that and frame the conversation to show how your product can enhance those aspects.

3. What are the biggest challenges and frustrations you face in your day-to-day?

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 is one thing you wish you could improve in your current processes?

Sometimes prospects feel their current operations are already running smoothly. If the answer is that there aren’t any real challenges or limitations, this question can help identify areas that aren’t necessarily problems but could be enhanced.

5. 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. 

Level Two: Gathering More Background Information

After the initial discovery conversation, you need to dive deeper into the challenges your prospect is facing and understand what they really want to fix about their current situation. These questions will help you identify your prospect’s goals, how they view success, and their ideal operating processes.


6.  What have you done to address your challenges so far?

This helps you understand what hasn’t worked for the prospect in the past so you can dispel concerns about these failures happening again later in the sales cycle. This is also 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.

7. What worked best with your previous solutions, and what issues have you run into?

Again, this is appropriate for more in-depth discovery. 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.

Perhaps your prospect has already tried to fix their problems with internal band-aids that have been unsuccessful. 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).

8. How would changing this process make your job easier?

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

9. What does your ideal process/situation look like?

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 technology partner. It also gives 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.

10. 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. 

Level 3: Eliminating Doubt & Concerns

At this point, you’ve likely established a need to buy a solution with your prospect. Now is when you start to get into what implementing a product or service would look like. These questions will help you identify potential barriers to adoption and any other concerns your prospect may have.


11. How would change potentially disrupt your current operations?

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.

12. 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 or as large as disrupting multiple teams’ operations.

13. 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.

14. What would implementing our solution look like at your company?

As you begin building out a final proposal for your prospect, you need to understand how they would use your product or service. For example, if you sell by the user/seat, you’ll need to identify how many licenses they’ll need. That will inform how you structure the deal and allow you to explain what that process would look like for the prospect.

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

This is a great way to end this stage of the conversation. It leaves the conversation open to the prospect to address any additional doubts or concerns before you move towards closing the deal. 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.

Level Four: Closing the Deal with Stakeholders

At this point in the sales cycle, you’re going to bring in additional decision-makers and buying committees. These questions will help you structure your proposals for different stakeholders in the prospect company and seal the deal.


16. How will the decision-making process work?

It’s critical to understand how your prospect buying committee functions. You need to know how the decision-making chain will operate, who will be involved, and what you can provide to make it run smoothly.

17. Who else should we involve in this conversation? 

This opens the door for prospects to bring in the individuals who will ultimately sign the dotted line—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 conversations with additional stakeholders and can help shape any specific demo scenarios you might need to close the deal. 

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

Chances are, you’ve already asked your prospect champion this question. As you bring in more stakeholders, it’s equally important to get their feedback on this. For instance, while budget might be a long-term roadblock, there could be a shorter-term hurdle that must be cleared first through the IT department. 

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

This is a good question given humans’ 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.

20. 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 the prospect needs and utilize your own internal sales resources to make the deal work.

Sales Questions to Avoid

Like open-ended questions that help you engage prospects and gather insights, there are also questions that can halt or derail a sales conversation, and in the worst-case scenario, result in a lost deal. 


You should avoid sales questions that are:

  • Focused on Your Company (Have you ever heard of us?): These types of questions pull the conversation away from the prospect. It’s no longer a conversation, and you’re talking at them, rather than with them.
  • Loaded/Biased Sales Questions (Why are you complacent losing money?): These questions include an assumption and can leave your prospect feeling a bit manipulated or pushed into an answer they’re not comfortable with. 
  • Yes/No Questions (Do you like your current processes?): This type of question allows a prospect to respond with a short one-word answer and requires multiple follow-up questions to get the information you could gather more easily with an open-ended question.

Creating Successful & Engaging Sales Interactions

Nailing down open-ended sales questions is an essential part of qualifying prospects and closing deals. The other part is identifying where your sales cycle succeeds and where it needs improvement. In order to create a successful sales cycle, you need to know where deals tend to slow in your pipeline, where reps may require additional coaching, and what an ideal sale looks like from start to finish. 

With an intelligent forecasting solution, you can do that and improve your forecasting accuracy. Learn more in our guide, “How an Accurate Sales Forecast Makes You a Hero to Your Entire Company.”

  • 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.