by Jenny Keohane

Top sales reps know that the key to a successful discovery call is centering the conversation around the prospect, their pain points, and how your solution will help them – this is done by asking questions.

But are you asking your prospects the right questions?

You want to avoid all questions that can be answered with a “yes” or a “no.” Your goal is to ask open-ended sales questions that involve in-depth explanations so you can grasp as much information as possible to tailor your sales pitch around them.

We’ll discuss 20 open-ended question examples, why they work, and what to listen for that will help accelerate your sales process.

1. What will make this a successful meeting for you?

At the very beginning of your meeting, you can immediately stand out by asking your prospect for their opinion and thoughts first. You can then jot down what they say, and make sure all points are covered throughout the discussion.

If they have a topic they want to discuss that aligns with a topic you were looking to discuss, make it about their topic. That way, you’re focusing the call around what they want to talk about, not you.

2. I’d like to discuss X, Y, and Z areas. Before we get started, what else would you like to cover in this meeting?

Another way you can immediately make the conversation about the prospect is by giving them a quick rundown of the areas you will be discussing and then ask if there are any additional areas they’d like to cover.

This sets the stage that right off the bat you’re already looking for their input and intake on the meeting structure – which gives you brownie points right from the get-go.

3. Walk me through your typical day-to-day activities in your role.

If you want to avoid asking directly what their pain points are, ask them to walk you through their day-to-day activities. This allows you to pinpoint certain aspects of their day where your solution can come into play.

They schedule a lot of meetings and your solution helps with that? Mention it.

Later in the conversation, use their description to intertwine your product into their day-to-day and how your solution can help them with certain tasks. Or use this question to lead into more tailored questions like – how much time do you spend scheduling meetings per day?

4. What are your company’s biggest priorities this year?

This open-ended question will give you better insight into the current state of their business.

This a heavy loaded question that will undoubtedly get your prospect discussing multiple points of focus that you can then implant why your product or service will help with any of these priorities.

5. Tell me about what you’re looking to accomplish.

They’re talking to you for a reason – what are they trying to accomplish? Let them express their visions and what they’re aiming to succeed in.

While your prospect is talking, listen for elements that your solution will bring value to. This immediately draws light on the fact that you want to help them accomplish their goals.

6. How have you tried to accomplish this in the past?

Have they tried other solutions before yours? What went wrong? This is another way of asking them what solutions they’ve tried in the past without directly asking for names.

If they mention a competitor – you know why your solution is better, discuss it.

Offer to share a case study or testimonial of a company similar to theirs that switched from the same competitor to you, what improvements did this bring?

7. What challenges have you faced in the past when trying to solve these problems?

This is another way of asking the question above. Your prospect will discuss any solutions they’ve tried in the past and what went wrong.

You know the challenges they faced are ones they can’t run into again – ensure them how your solution avoids those challenges and why it will be different this time.

8. What’s prompting you to do something about this now?

It’s important to gather insight into the business’ timeline and why they’re initiating this change now.

Did something specific happen that prompted them to act now? Did they get budget approval? Is their business growing? Have they shifted focus? This is an important aspect to identify.

9. Companies similar to yours have discussed issues around X, Y, and Z. Are these currently affecting you and your business?

If you’re at a standstill with your prospect and haven’t been able to get them to fully discuss areas of concern for their business, this question can help.

By discussing similar companies, you assure them that they’re not alone. The fact that other companies are experiencing the same problems as they are can help make it easier for them to come to terms with their struggles.

Your goal is to get your prospect as comfortable as possible talking about certain aspects of their business.

10. What does your current process look like?

This allows you to view whether or not your solution fits into their current process – not everyone is fitted and qualified for your solution.

If you’re selling sales enablement software – ask them about their current sales process so you can identify areas where your solution will come into play to help shorten the length of their sales cycle.

What’s working well in their current process and what isn’t working? How will your solution change the pros and cons, it’s all-important.

11. What are your team’s current goals?

Team goals are different than business goals. How can your solution help the team be more productive and collaborative?

This question also leads to the next question which will identify blockers the team is currently facing that are getting in the way of these goals.

12. What’s holding your team back from achieving your goals?

This is where you can identify any roadblocks.

What is getting in the way of the team achieving their goals – can your solution help overcome these obstacles?

From this point forward, tailor your questions around these goals and how elements of your solution will help the team reach their goals faster.

13. You mentioned frustration around X. Can you elaborate?

Not every prospect will fully dive in on topics they’ve discussed. Pick a frustration they mentioned and ask them to elaborate further, this can help uncover aspects of the problem.

Your goal in asking these open-ended sales questions is to get your prospects talking, but this isn’t the case all the time. If they need that extra boost, ask them to elaborate. Be specific. Don’t let it slip by without getting them to express an important element.

14. What steps do you need to take in order to make a decision and purchase your chosen solution?

This question is another way of asking how does their decision-making process work.

To avoid any objections from arising later in the sales process, this is an important question to ask. The buying process differs between companies – understanding the decision-making process early on is essential and alters your future conversations.

This helps you identify all stakeholders involved so you can ask to include them in the following calls. That way you’re not wasting either of your time and can communicate your message to all decision-makers.

15. When would you ideally like to implement a solution for the team?

What does their timeline look like? This is another important qualifying question. Are they looking to implement this solution in days, weeks, months, years?

If they’re looking to start at a later date – you can push on the urgency now. But it’s important to know their timeline so you can act accordingly and forecast opportunities accurately.

16. Do you have any worries that are holding you back?

Get any worries or doubts out of the prospect sooner rather than later.

By asking this open-ended question, they reveal any back-of-the-mind doubts that could arise later in the sales process – resolve them as soon as possible so you’re not wasting either of your time and you can help ease any confusion right off the bat.

17. Do you foresee any pushback from your colleagues against the solution?

Sometimes the person you’re talking to can have a different perspective than others. If you ask if there are any colleagues that are portraying doubt, you can get them involved immediately.

Ask if they can join the next meeting so you can talk to them directly, ask for their email to get in touch, etc. There are many ways you can go about involving everyone. And this question can also help reveal if there are other decision-makers that haven’t been identified yet.

18. Do you have any further questions that we didn’t touch on this meeting?

Never end the meeting without asking for questions.

Leaving with uncertainty reflects poorly on the call. You want the prospect to communicate every aspect clearly to their team with confidence.

19. Which areas of our solution do you still have questions about?

It’s impossible to cover every aspect of your solution in one short call – typically the area they have more questions about is the area they’re most invested in and is most crucial for them in making this decision. This is an important insight to gain before the end of the call.

20. What are you thinking about for the next steps?

Allow the prospect to give their input on the next steps – and then chime in your opinion after.

By asking them for their thoughts first – you gather insight on how the call went for them, how urgent the situation is, and their level of interest.

After their opinion, you can suggest your own action items.

Final Tip: Make it conversational

Use these 20 open-ended sales questions to get prospects talking and bringing the conversation to more of a discussion than a Q&A.

Based on their responses, ask questions accordingly. Don’t be a robot, make the call as conversational as possible. Listen, ask questions about what they’re saying, rephrase what they say, and make it clear that you’re listening.

Remember – getting your prospects to talk is a win-win. It not only helps you better understand your prospect but will increase the likelihood that the prospect looks back on the conversation in a positive light because everyone likes talking about themself.