41 Powerful Open-Ended Sales Questions to Use Today

min read
May 17, 2024

Sales is more about listening. 

When you listen, you find what potential customers desire.

However, you need to ask the right questions to get to the crux of customers’ requirements and expectations. Open-ended sales questions are the best way to understand what prospects truly need. 

Let’s dig deeper into open-ended questions and how to craft them perfectly in prospect conversations. 

What are Open-Ended Sales Questions? 

Open-ended sales questions are queries prospects cannot answer with a simple “yes” or “no.” They often think and provide thoughtful responses when you ask these questions. You can spark interesting conversations through them to uncover prospects’ actual pain points and needs. 

For example, asking, “How do you feel about the recent product updates?” opens the stage for prospects to express themselves. You can then use their responses to identify opportunities and challenges and address them in conversations. 

Conversely, if you ask, “Are the latest product updates beneficial for you?” The answer will be simple “yes” or “no,” providing no context to advance the discussion.

Advantages of asking open-ended sales questions

Below are some key advantages of asking open-ended questions in sales conversations. 

Get Unexpected Insights

Asking open-ended sales questions turns a conversation into a podcast, but not literally. Simply put, it lets salespeople and prospects explore the depth of a topic in conversation rather than sifting through its tip with a “yes” or “no” paddle.

Build Trust and Rapport

Potential buyers share when you patiently hear. Active listening fosters trust, making prospects comfortable revealing previously unexpressed challenges.

These conversations amplify your prospects’ trust in you, building a strong relationship that opens up new upselling and cross-selling channels. You can ask questions like, “What services or support would make you more successful in your work?” This will open up an opportunity to upsell plans that involve managed services or support from a dedicated account manager. 

Recognize Customer Pain Points 

Sometimes, customers might not even be fully aware of their problems, or they might hesitate to voice them directly.

Open-ended questions naturally lead to follow-up questions. As the prospect elaborates on their initial response, you can ask further open-ended questions to delve deeper and uncover the root causes and specific impacts of their pain points.

Identify Sentiments

Open-ended sales questions unwrap prospects’ feelings, motivations, challenges, emotions, and opinions, which vary for every prospect you work with. This allows you to personalize sales conversations based on them, offering a better experience to potential buyers. 

The content of a prospect's response to an open-ended question reveals their emotional state. Words they choose, the tone of voice (if spoken conversation), and the length of their response can all be indicators.

You can analyze sales conversations to identify the following emotions: 

  • Frustration. Look for words like "difficult," "frustrating," "inefficient," or "time-consuming." A short, annoyed response might also suggest frustration.
  • Excitement. Words like "excited," "opportunity," "growth," or "improve" might indicate a positive sentiment. A longer, enthusiastic response could also be a clue.
  • Apprehension. Look for words like "worried," "concerned," "uncertain," or "risky." A hesitant or cautious tone could also suggest apprehension.

Understanding prospects’ sentiments lets you personalize the sales process, giving you a better chance to seal the deal.

How to Craft Open-Ended Sales Questions

Use the 5W1H framework to craft open-ended sales questions. 5 “W” refers to who, what, where, when, and why, and “H” represents how. These are fundamental question words that your sales team should use to frame questions while assisting prospects. 

Investigators and journalists typically use this framework to research a story. However, it’s also implemented in many areas, such as project planning, management, and sales. 

Suppose you’re in a sales dialogue with a prospect. Here’s an example of how you can use the 5W1H approach to frame open-ended questions for sales. 

  1. Who will benefit the most from the process and why? 
  2. What do you think is your biggest hurdle in implementing this approach? 
  3. Where are the pinch points in this process?
  4. When can we proceed with this implementation? 
  5. Why does your current solution fail to deliver? 
  6. How do you plan to implement the product across the enterprise? 

These are a few basic questions. You can easily experiment with the five Ws and one H to create open-ended sales questions for all sales cycle stages

Top 41 Open-Ended Sales Questions Examples 

Below are a few examples to inspire you to create open-ended questions for sales.

We have categorized these questions to help you choose the best based on your company size and sales stage. However, these questions aren’t exclusive to a category or stage. You can use it as you see fit in the sales process.

Qualification Questions 

These questions help the sales team assess whether a prospect complements their ideal customer profile (ICP). If there’s a match, sales teams prioritize engaging such customers, maximizing their chances of closing a deal

At the sales qualification stage, you can ask the following open-ended questions:

For Startups and SMBs

  • “What business problem are you trying to solve?”
  • ”What are your pain points?”
  • ”What are the pain points of users using this product?” 
  • ”How do you currently manage this problem?” 
  • ”What motivated you to look for a solution?”
  • “When are you planning to purchase the product?”
  • ”When do you want to onboard your team?” 

For Mid-Market and Enterprise Companies

  • ”What sort of budget would you use to solve this problem?”
  • ”How soon do you think you’ll have the budget to onboard a new tool?”
  • ”What does the purchase approval process look like?”
  • ”Who will be the key decision-makers in purchasing, and how would they use the product?” 
  • ”How effective is your current solution in solving the problem?” 
  • ”How much are you currently spending to solve this problem?” 
  • ”How long will it take for you to make a decision?” 
  • ”Where would you like to host the product?”

Need Discovery Questions

These questions provide more content to salespeople to help them suggest the best solution to their prospects. The questions dive one step deeper into exploring prospects’ needs and allow salespeople to give the right information necessary to keep potential customers engaged

For Startups and SMBs

  • “What do you want to achieve by onboarding the product?”
  • “What does your ideal solution look like?” 
  • “When did you start having these problems?”
  • “What will you need from me to make the decision easier?”
  • “How can I make this meeting more useful for you?”
  • “What would you like to know more about that I haven’t covered yet?”
  • “What are your thoughts or concerns so far?”

For Mid-Market and Enterprise Companies

  • “Do you face any other challenges you haven’t spoken of so far?” 
  • “How can we help to support your team in managing the change?” 
  • “What would you need to finalize our partnership?”
  • “How is the problem affecting revenue or costs?”
  • “How would stakeholders assess our solution’s success?”

Tip: You can create a demo agenda before connecting with the clients to ask better questions and give them context to make the conversation more effective.

Solution-Specific Questions 

Salespeople ask solution-specific questions to understand potential buyer’s expectations regarding the type of solution they’re looking for. Active listening plays a crucial role here. It lets you frame these questions according to customer’s previous responses, helping you suggest the best solutions.

For Startups and SMBs

  • “When would you like me to walk you through the product? Or would you prefer an interactive demo so you can experience it independently?”
  • What did you do in the product to solve your problem? What route did you take to solve it? 
  • What was your experience when you tried XYZ products? 
  • What would success look like for you?

For Mid-Market and Enterprise companies

  • What are the different knowledge gaps in your department, and how do you plan to bridge them?
  • Do you have a set expectation in terms of the product’s time to value? 
  • How would you like to train your team on the new product? 

Strategic Questions

Below is a list of open-ended sales questions that sales leaders ask to find, engage, and close the best deals in their tenure. 

For Startups and SMBs

  • “How does solving this challenge fit into larger business objectives?” 
  • “What outcomes would make this investment worth it?”
  • “What potential deal-breakers can prevent us from working together?”

For Mid-Market and Enterprise Companies

  • “Why did you consider our product/service just now?”
  • “What are the barriers you might face when you scale your business?”
  • “What are the business objectives you plan to achieve this year? How does our product fit into it?”
  • “Why did you consider our product among others on the market? What was your one primary differentiator?”

5 Mistakes to Avoid While Asking Open-Ended Sales Questions

Open-ended questions can backfire if not phrased properly. Avoid these mistakes when framing them for leads, prospects, and opportunities. 

1. Answering It Yourself

Suggesting answers to your prospect’s question might seem a good way to guide the conversations. However, it’s not advisable. It limits what prospects can share with you and provides only a part of the actual information. 

Practice active listening and being attentive to what your prospects share without breaking their flow. This will bring out the real story they wanted to narrate without tainting it with your suggestions. 

2. Being Unnecessarily Salesy

Conversations should feel natural to get maximum value from them. Don’t try to sell whenever the prospect expresses a problem your product can solve. When you hear their problem, try exploring it further through open-ended questions. 

It shouldn’t be like when a buyer expresses their pain, and you go, “Our product can solve it. Try it now,” or “Let me give you a demo to show how our product solves it.” Keep these nudges for later when you understand their pain point and clearly comprehend what you can offer to address them. 

You can ask questions like, “How long have you been struggling with (problem), and why did you wait until now to find a solution?” This will show a better picture of where they’re coming from. 

Moreover, being consultative will tremendously help you build rapport with prospects. 

Suppose your prospect takes the lead in a conversation. With your guidance, you can ask questions to encourage them to explore the product themselves. This is how reverse demo works. 

You give them temporary access to self-guided demos, where they experience the platform themselves. This enables them to solve their problems with your product support, making them a true leader in the story. 

3. Making a Conversation Feel Like an Interrogation

When you keep asking questions without establishing proper context, it feels like an interrogation. You’re not playing a rapid-fire quiz with your prospects; instead, you want them to take the time to respond. 

However, when you have prepared a list of questions already and need them to answer all, you might turn the conversation into a rapid-fire round. But this is an innocent oversight and quite natural. 

To avoid this, be attentive to prospects' answers and ask more follow-up questions to make them feel you’re invested in the discussion. Do not ask these questions like a robot. 

4. Phrasing Your 'Whys' Casually 

Asking a “Why” is tricky. You want the prospects to give more information but without sounding accusatory with your tone. For example, “Why didn’t you look out for a solution until now,” is a harsh way to find the right information. Turn the “why” into a “what” statement in such a case. 

For example, “What was the reason behind exploring a solution now and not earlier.” This sounds genuinely curious and not accusatory. 

Ask your “Why” questions intelligently. It’s advisable to limit the number of times you ask such questions. To be more conversational, try positioning them as “What” questions. 

5. Being Unattentive to Customers’ Body Language

Look for signs of discomfort or disinterest when they appear. If a prospect isn’t engaged, they’ll present these signs. When conversing with prospects over video conferencing, you can see if a person has raised eyebrows, which means they’re interested in the discussion.  If you see a frowning face, stepping back and letting the customer navigate the conversation is best.

When talking on the phone, look for heavy exhales or quick rises in your voice to notice any signs of discomfort. 

These non-verbal cues will allow you to drive conversations effectively while keeping prospects engaged. 

How Can Storylane Help You Ask Better Questions?

When you share a Storylane interactive demo with the prospect before the discovery call, you get to analyze how they engage with it. The behind-the-scenes demo insights shed light on which product features grab the most attention and what problem the prospect might be trying to solve. This helps you ask better questions, leading to more productive conversations. 

You’ll get insights like: 

  • Demo engagement at an account level
  • Account insights to enrich viewer data
  • Number of times people interacted with the demo
  • When was the last time a lead viewed a demo
  • Percentage of guided steps a view has completed

Take a Storylane free trial and explore how it makes your sales conversations more productive. 

Open-ended sales questions FAQs

1. What are open and closed-ended questions in sales?

Open-ended questions give the person you are asking the opportunity to answer freely. Conversely, closed questions usually limit answers to a few options.

2. Why should you use open-ended questions in sales? 

Open-ended questions allow sales reps to create a healthy dialogue. They gently encourage the customer to share information showing their pain points.

"Previously, there was scope for error and we’ve gone from a process that could be time consuming and painful to a process that’s super quick."
Supercharge your funnel with Interactive Demos
Book a demo
Revolutionize your sales game with interactive Product demos
Take a tour

What’s a Rich Text element?

The rich text element allows you to create and format headings, paragraphs, blockquotes, images, and video all in one place instead of having to add and format them individually. Just double-click and easily create content.

Stay ahead of the sandbox curve with a superior demo environment
Try Storylane
Capture more leads and close more deals with interactive demos Take a tour
"Previously, there was scope for error and we’ve gone from a process that could be time consuming and painful to a process that’s super quick."

"Previously, there was scope for error and we’ve gone from a process that could be time consuming and painful to a process that’s super quick."


Stay ahead of the sandbox curve with a superior demo environment
Try Storylane
Stay ahead of the sandbox curve with a superior demo environment
Get the Storylane Advantage
Learn more about how Thrillark Procured over a 60% Increase in
Button Text
Learn more about how Thrillark Procured over a 60% Increase in
Button Text
Capture more leads and close more deals with interactive demos.
Take a tour