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20 Best Open-Ended Sales Questions to Steal for 2024

Open Ended Sales Questions

It’s a moment you never want to experience…but it still happens all too often:

The moment you’re in that important sales conversation and you can’t think of the right question to ask next.

You know that asking the right questions can unlock valuable insights into your potential customer’s pain points.

But let’s be real—it’s hard.

You might be asking:

“What questions will help me truly understand my customer’s needs?”

“How can I make sure my questions spark meaningful discussions and not just one-word responses?”

“What’s the secret to getting customers to open up, share their challenges, and see my solution as the perfect fit?”

If so, you’re in the right place. 

In this guide we’re here to help you answer these questions. We’ll give you the tools and techniques to master the art of asking open-ended questions. 

You’ll discover a list of 20 of the best open-ended sales questions to up your sales game in 2024.

So if you’re ready to revamp your sales approach, break through barriers, and turn potential leads into satisfied customers, keep reading. 

It’s time to up your sales game and start closing deals like a pro.

Open-Ended Sales Questions vs Close-Ended Sales Questions 

In sales, the right questions can be the difference between a successful deal and a missed opportunity. 

It’s crucial to understand the distinction between open-ended and close-ended questions—and even more important to know how to use each effectively in your sales calls.

What’s the Difference?

Good open-ended questions invite your customer to share their thoughts, feelings, and experiences. 

These questions often start with words like “what,” “how,” “why,” or “tell me about.” 

For example, “What challenges are you currently facing in your business?”

On the other hand, close-ended questions lead to a straightforward answer—often a simple “yes” or “no.” 

They typically begin with words like “are,” “is,” “do,” or “can.” 

An example might be, “Can you meet the project deadline?”

The Strategy Behind Each

In a sales call, understanding when and how to use these two types of questions is crucial.

Open-Ended Questions

These are your conversation starters. 

They encourage your potential customer to open up, share their needs, and express their pain points. 

The beauty of open-ended questions lies in their ability to create a dialogue, build rapport, and uncover valuable information.

Close-Ended Questions

These questions have their place too. 

They’re handy for confirming specific details and guiding the conversation down a particular path. 

While they may not provide in-depth insights like open-ended questions, they serve a purpose in maintaining control and clarifying crucial points.

In your sales calls, it’s not about choosing one over the other, but rather using them both at the right time. 

Knowing when to ask open-ended discussions and when to use close-ended questions for clarification is a great skill to have.

So, as we dig deeper into open-ended sales questions, keep in mind that both types have their roles to play in sales.

How Are Open-Ended Questions Best Used During the Sales Process? 

Now, let’s get practical. 

We’ve discussed the difference between open-ended and close-ended questions, and you might be wondering how to make open-ended questions an asset in your sales process. 

Here are five tips to help you get the most from these questions and keep your customers engaged:

Tip #1: Build Rapport

Think of sales calls as friendly conversations rather than business transactions. 

Keep in mind that selling is helping, not forcing.

So, begin with a simple icebreaker like, “How’s your day going?” It helps break the ice and set a relaxed atmosphere.

Also, according to a study, asking questions like “How have you been?” during the call increases the success rate by 6.6x

Tip #2: Outline the Path

Before diving into your sales pitch, give your customers an idea of what’s coming. 

Outline the topics you’ll cover, so they know what to expect. It’s like setting an agenda for a meeting—it keeps everyone on track.

Tip #3: Dig for Insights

Only 37% of prospects in a HubSpot survey felt salespeople who’d made cold calls to them had delivered information relevant to their needs. 

Usually, the reason for this is not having enough info for tailoring the pitch.

Because to tailor your pitch effectively, you need to know your customer’s needs, goals, and challenges. 

Ask probing questions that reveal their pain points. 

For instance, you can ask, “What’s the biggest challenge your business is facing right now?”

Tip #4: Build Trust

During the transition phase, focus on trust-building. 

Instead of taking charge, let your customer express their thoughts and concerns. Show genuine interest in their perspective, ask more questions, and reassure them that you’re here to help.

Tip #5: Solve, Don’t Sell

The pitch isn’t about showcasing your product; it’s about solving your customer’s problem. 

Concentrate on the transformation your product can offer. Start by making a promise tailored to their needs, making them feel you’re addressing their unique pain points.

By following these five practical tips, you can make open-ended questions work seamlessly in your sales calls. 

The 20 Best Open-Ended Sales Questions for Your Call

Okay, now we’re diving into the good stuff—the 20 best open-ended questions for sale in 2024. 

Feel free to steal them and make them your own.

Question #1: What Are Your Biggest Goals for the Year?

This question gets the ball rolling by encouraging your customer to share their aspirations. It helps you align your pitch with their objectives.

Question #2: What’s Happening in X That’s Preventing You From Reaching Your Goal?

By asking this, you’re diving right into their problems. Understanding their pain points is key to positioning your product as a solution.

Question #3: How Do You Envision Success with Our Product/Service?

This question helps you visualize the end goal together. It’s all about making your customer feel that success is within reach.

Question #4: Can You Share Some Past Experiences with Similar Solutions?

Learning from their previous experiences can provide valuable insights into what they’re looking for and what they want to avoid.

Question #5: What Has Stopped You From Achieving Your Goals So Far?

This question uncovers potential roadblocks and challenges your customer has faced, which can guide your sales pitch.

Question #6: How Would Solving [Specific Challenge] Impact Your Business?

This question focuses on a specific challenge, making your pitch more targeted and relevant to their needs.

Question #7: What Does Your Ideal Solution Look Like?

This question helps you understand their vision of the perfect solution, which can guide your product presentation.

Question #8: What Are Your Top Priorities for the Upcoming Quarter?

It’s all about aligning your pitch with their current priorities, making your offer more compelling.

Question #9: How Do You Envision Implementing This Solution in Your Workflow?

Understanding how they plan to integrate your product into their workflow provides insights for a tailored pitch.

Question #10: Can You Share Some Key Milestones You Hope to Achieve?

This question helps you visualize the journey together and demonstrate your commitment to their success.

Question #11: Are There Any Concerns or Obstacles You’re Worried About?

Addressing concerns upfront shows your customer that you care about their worries and are ready to provide solutions.

Question #12: How Do You Imagine the Impact on Your Team or Business Culture?

This question focuses on the bigger picture, helping your customer see the transformative potential of your solution.

Question #13: Can You Tell Me About a Recent Success Story in Your Business?

Hearing about their successes can reveal their strengths and what they value, allowing you to align your pitch accordingly.

Question #14: What Would a Perfect Outcome with Our Solution Mean to You?

This question encourages your customer to paint a vivid picture of success, making it more tangible and appealing.

Question #15: How Do You Evaluate the Effectiveness of a Solution Like Ours?

Understanding their criteria for success helps you align your pitch with their expectations.

Question #16: What Would Be the Ideal Timeline for Implementing a Solution?

This question sets the stage for discussing the implementation process and managing their expectations.

Question #17: Can You Share Any Specific Metrics or KPIs You’re Focused On?

Metrics matter, and this question helps you connect your solution to their key performance indicators.

Question #18: How Do You See Our Solution Fitting into Your Budget?

Budget concerns are common, and addressing them early on can build trust and transparency.

Question #19: What’s Your Current Framework for Making Decisions?

This question gives you insights into the decision-making dynamics within the organization, helping you navigate the sales process effectively.

Question #20: What Would a Seamless Partnership with Us Look Like to You?

This question encourages your customer to imagine a harmonious relationship, which can be a powerful motivator for closing the deal.

These 20 good open-ended sales questions are powerful. 

Use them wisely, and watch how they transform your sales calls into engaging and productive conversations.

How to Choose the Right Open-Ended Questions for Your Sales Call 

With the 20 open-ended sales questions at ready, you need to know how and when to use them effectively. 

Rather than shooting questions in the dark, you have to be precise and guide the conversation to your customer’s pain points. 

Let’s explore detailed steps and examples of how to achieve this:

1. Build a Connection First

Before diving into your sales pitch, it’s crucial to establish a connection with your customer

Because if you start too aggressively, you could drive 84% of buyers away.

Begin by engaging in a friendly conversation. Ask about their day or share a common interest. 

This rapport-building phase helps create a comfortable atmosphere. You have to remember this because people tend to open up more when they feel a genuine connection.


You: “Hi there! How’s your day been so far?”

Customer: “Not too bad, thanks for asking. It’s been quite busy.”

You: “I totally get that. Busy days can be a handful. By the way, do you have any exciting plans for the weekend?”

Customer: “Oh, I’m planning to attend a local event with my family. Should be fun!”

You: “That sounds great! Spending time with family is always a good choice.”

2. Listen Actively

Listening is a powerful tool in sales. 

Pay close attention to what your customer is saying, and actively listen. 

Every word they utter is a potential cue for your next question. This shows that you’re genuinely interested in their unique situation.

3. Ask Your Open-Ended Questions

Instead of firing closed-ended, yes-or-no questions, ask open-ended ones that invite detailed responses. 

These questions let your customers open up about their needs, challenges, and aspirations—giving you valuable insights to tailor your pitch effectively.

Here, you can use the 20 open-ended questions we talked about whenever you see fit. 

This is why it’s very important to listen actively. You can’t just ask random open-ended questions to your customer.

You have to tailor it to their problems.


Closed-Ended: “Are you satisfied with your current solution?” ❌

With this question, you’re not really digging deep to the problem. Your customer can just answer it with yes or no. That doesn’t give you information to solve their problems.

Open-Ended: “Can you tell me about your experience with your current solution? What’s working well, and where do you face challenges?” ✅

Can you see the difference? This one encourages your customers to talk about their pain points—something that’s important for your pitch and for solving their problems.

4. Encourage Storytelling

People love to share stories, and storytelling can reveal a wealth of information. 

Encourage your customers to recount their experiences, share anecdotes related to their business, or discuss specific situations they’ve encountered. 

These stories can lead to deeper insights into their needs, challenges, and pain points.


You: “Do you have any memorable experiences with your current software?”

Customer: “Well, there was this one time when our software crashed right before a big client presentation…”

You: “Oh, that must have been stressful. Can you walk me through what happened and how it affected the presentation?”

Again, you have to make it easy for them to open up about their pain points.

5. Follow the Flow

Conversations have a natural flow, and it’s essential to go with it. 

If your customer mentions a particular challenge or goal, seize the opportunity to delve deeper. Ask follow-up questions that expand on their initial responses. 

This helps you understand their situation more comprehensively.


Customer: “We’ve had issues with employee communication.”

You: “I understand, employee communication is crucial. Could you tell me more about the specific challenges you’ve encountered in this area?”

In this simple example, your customer expressed a concern. And when they do that voluntarily, you have to take the flow and encourage their feelings on that.

It also helps you a lot—since the problem comes from their mouth.

6. Use Their Language

Mirroring your customer’s language and terminology can make them feel understood. 

If they use industry-specific terms or phrases, incorporate those into your questions. 

This demonstrates that you’re on the same page and understand their unique context.

For example, if you’re working with someone in the digital marketing field, words like “buyer persona,” “SEO,” or “Google Ads” might pop up in the conversation.

In these cases, you have to show that you’re on the same page with them. This is why researching the field is important.

7. Be Patient and Empathetic

Not all customers will immediately open up about their challenges and pain points. 

Some may be hesitant or reluctant to discuss their problems. 

In such cases, patience and empathy are your allies. Gently encourage them to share by showing understanding and a genuine interest in helping.

People are smart. They will sense it if you’re trying too hard too sell them.

8. Offer Solutions Casually

While your primary goal is to gather information, if the opportunity arises, you can subtly mention how your product or service can address the challenges they’ve revealed. 

Be careful not to push a hard sell at this stage; instead, casually hint at how your solution aligns with their needs.


Customer: “We’ve been struggling with outdated software that doesn’t meet our needs.”

You: “I appreciate you sharing that. It’s interesting that you mention outdated software. Our product has helped many clients in similar situations by providing modern and customizable solutions.”

By following these steps and examples, you’ll create a conversation that naturally uncovers your customer’s pain points and makes it easier to present your product as their solution. 

Remember, effective sales conversations are not just about talking but also about listening and understanding.

Close Your Sales Calls With These 20 Questions

To sum it all up, here’s what you need to take away from this guide on using open-ended sales questions effectively.

  • Sales isn’t about pushing your products; it’s about having a conversation, understanding your customer, and offering solutions that truly meet their needs. 
  • Asking the right questions is your key to success—and we’ve provided you with a comprehensive list of these open-ended questions.
  • The real power of these questions isn’t in what you ask but in how you listen. 

Our message to you is simple: put these open-ended questions to work. Use them in your sales conversations and watch how they make a difference. 

Have deeper connections with your customers, empathize with their situations, and provide solutions that genuinely connect with them.

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