60+ Sales Questions to Elevate Your Closing Rates

The quest to find your ideal set of sales questions often begins with a simple Google search. (Sound familar?) 

However, this seemingly easy step can quickly become overwhelming as hundreds of suggested questions flood your screen.

To make matters worse, not every question you encounter will integrate into your sales strategy, especially in a B2B context where the stakes are high and the sales cycles are lengthy.

That’s why we compiled this comprehensive list of the top 60+ sales questions that will actually boost engagement and conversions. 

How do we know? Because for the past 15 years, we’ve used questions like these to generate leads and close deals for B2B companies worldwide. 

But that’s not all. 

You’ll also discover expert-backed strategies to refine your questioning techniques and elevate your sales conversations.

So, what are you waiting for? Let’s get started.

How to Ask Probing B2B Sales Questions

The main goal of asking questions during a sales conversation goes beyond simple information gathering. It’s about building rapport, identifying specific client needs and challenges, and steering the conversation toward applicable solutions.

Effective questioning positions salespeople as trusted partners, adept at addressing their prospects’ unique concerns. Therefore, an impactful sales question should be:

1. Thought-Provoking: encouraging the prospect to think deeply and provide substantial insights
2. Relevant: connecting directly to the prospect’s business context
3. Strategic: guiding the discussion toward areas where you can deliver significant value

Types Of Sales Questions To Ask A Prospect

Navigating a sales dialogue effectively requires a toolkit of varied question types, each tailored to elicit specific kinds of information and responses that drive the conversation toward a successful outcome.

Let’s take a look at the different types of sales questions you could ask your prospects: 

1) Open vs. Closed Questions

Open-ended questions are designed to encourage a full, meaningful answer using the subject’s own knowledge and feelings. These are great for getting a deeper insight into the prospect’s needs and challenges. For example:

• “What are the main challenges you face with your current process?”
• “How do you see this solution impacting your day-to-day operations?”

In contrast, closed-ended questions require a short, direct response and are useful for gathering specific data. These are also referred to as “yes or no” questions and are a great way to confirm details and summarize understandings. For example:

• “Do you currently use a CRM system?”
• “Is there a budget set for this project?”

2) Exploratory vs. Confirmatory Questions

Exploratory questions aim to uncover as much information as possible, allowing you to discover new opportunities and insights and push the boundaries of what is already known. Examples include:

• “What strategies have you considered to address this issue?”
• “Could you explain more about how that process works currently?”

Confirmatory questions are used to verify information that the prospect has provided, ensuring that both parties are on the same page and that you have understood their statements correctly. For example:

• “So, you’re looking for an improvement in efficiency, correct?”
• “You mentioned that cost is a major concern; is that right?”

3) Strategic vs. Tactical Questions

Strategic questions address the broader business outcomes and objectives, linking your discussions to the bigger picture of the prospect’s company. For example:

• “How does this initiative align with your overall business goals?”
• “What long-term outcomes are you hoping to achieve with this solution?”

Tactical questions, on the other hand, focus on the specifics of how things will be done or have been done. These questions deal with the immediate, practical details that influence day-to-day business operations. Examples include:

• “Who will be the main user of this solution?”
• “What specific features are necessary for you to meet your immediate goals?”

4) Reflective Questions:

Reflective questions are used to paraphrase or summarize what the prospect has said, confirming understanding and demonstrating active listening.

• “So, if I understand correctly, your main concern is reducing operational costs?”
• “You’re saying that improving customer service response times is a priority, right?”

60+ Sales Questions By Stage: What And When to Ask

The journey through the sales funnel is marked by distinct stages, each demanding a unique set of questions. By crafting questions that resonate with the depth and complexity required at each step, you can steer prospects through their buying journey and ensure that they’re moving toward closing the deal.

Here’s how to categorize sales questions based on different stages in the B2B sales funnel:

1) Discovery Questions

Discovery questions are used to gather comprehensive information about the prospect’s business, their specific needs, challenges, and goals. These questions open the dialogue and set the foundation for the relationship.

Examples:

• What prompted you to explore solutions in this area at this time?
• Can you walk me through your current process related to this issue?
• What are the biggest challenges you’re facing in your industry today?
• How are these challenges impacting your day-to-day operations?
• What goals do you hope to achieve by solving these challenges?
• Who else in your organization is affected by these issues?
• What have you tried previously to address this problem?
• What did you like and dislike about the solutions you’ve tried before?
• How does this priority fit into your broader company objectives?
• Can you describe the decision-making process for initiatives like this?
• What would an ideal solution look like for you?

2) Rapport-Building Questions

This type of question is designed to create a personal connection and build trust between the salesperson and the prospect. Rapport-building questions often touch on lighter, more personal topics or common interests.

Examples:

• How did you get started in this industry?
• What’s the most rewarding part of your job?
• I noticed you attended [Event/Conference], what was your biggest takeaway?
• What do you find most challenging about your role?
• What recent changes in your industry have you been excited or concerned about?
• How do you see your company evolving in the next few years?
• What personal accomplishments in your career are you most proud of?
• Outside of work, what are you passionate about?
• How does your company value differ from the competition?
• What impact has recent technology had on your business processes?

3) Qualifying Questions

Qualifying questions help you quickly determine whether the prospect is a good fit for the product or service. Such questions assess the prospect’s ability to purchase and their readiness to make a decision.

Examples:

• What is your timeline for implementing a solution?
• Who else will be involved in making this decision?
• What budget has been allocated for this project?
• What are your criteria for selecting a solution?
• How urgent is the need to implement a solution?
• What are the key performance indicators you’re hoping to improve?
• Can you describe your decision-making process?
• What other solutions are you currently considering?
• How does this project align with your strategic goals?
• What would prevent us from moving forward with this?

📌 If you would like to learn more about the sales qualification process, check out our how-to guide. 

4) Trial Closing Questions

Trial closing questions enable you to gauge the prospect’s interest level and readiness, while also addressing any lingering hesitations. Unlike direct closing questions, these are designed to elicit opinions and insights, rather than straightforwardly pushing for a commitment.

Examples include:

• Based on what we’ve discussed, how well does our solution meet your needs?
• Do you see any areas where our solution falls short of your expectations?
• Is there anything preventing us from taking the next steps?
• How do you feel about the timeline for implementation we proposed?
• Are there any additional features you would need to see included?
• From what you know now what reservations would you have in recommending this solution?
• What additional information would you need to make a decision?
• If we addressed [specific concern], would you feel ready to proceed?
• How does this proposal align with your budget expectations?
• What’s one thing that would make this decision easier for you?

5) Closing Questions

Closing questions are direct and typically used when moving the prospect toward making a buying decision. You should ask a closing question whenever you sense that the prospect is ready to convert and proceed with their purchase decision.

Examples:

• Are you ready to move forward with this solution?
• What steps should we take to finalize this agreement?
• Can we set a date for the implementation to begin?
• Who will need to be involved from your team as we finalize details?
• Shall we go ahead and draft the contract?
• Would you like to schedule a follow-up meeting to discuss any outstanding issues?
• How would you like to handle the provision of services?
• Is there anyone else we need to bring into this discussion before we proceed?
• Can we confirm the terms so I can draw up the paperwork?
• What documentation can we provide to help you make this decision?
• Would you require any further demonstrations or data before finalizing?

6) Objection-Handling Questions

These questions are crucial for addressing and overcoming any concerns or objections the prospect might have. Effective objection handling can often be the difference between losing and closing a sale.

Examples:

• What specific concerns do you have about our solution?
• Is there a particular aspect of our proposal that doesn’t meet your needs?
• What could make this solution a better fit for your company?
• Are there any issues about the pricing structure that we could revisit?
• What would need to change for you to feel comfortable moving forward?
• Can you help me understand why this isn’t a good fit so we can find a better solution?
• Do you need more information or data on any part of our proposal?
• What reservations are holding you back from making a decision?
• How does this decision align with your strategic priorities?
• Are there other stakeholders we should involve in this discussion?

5 Mistakes To Avoid When Crafting Sales Questions

1) Assuming Answers with Leading Questions

Leading questions can subtly influence how a prospect responds, potentially skewing valuable information and leading to misguided sales strategies. These questions assume a specific answer and often limit the prospect’s responses, which can result in inaccurate assessments of their needs and interests.

To avoid this:

Frame your questions to be more open and neutral. Instead of saying, “Don’t you think our product could solve your issue?” ask, “How do you currently handle this issue, and what are you looking for in a solution?” This encourages genuine, unbiased feedback from the prospect and makes them feel more valued.

2) Conducting Interrogations Instead of Conversations

When questions are fired one after the other without giving potential buyers a chance to respond, the whole interaction can feel more like an interrogation than a conversation. This approach often intimidates prospects and shuts down open communication, leading to lower conversions and reduced customer satisfaction.

To avoid this:

Balance your questioning with active listening to give prospective clients a chance to express themselves. Allow the conversation to flow naturally and encourage dialogue by responding to answers with follow-up questions or comments that demonstrate understanding. For instance, “Based on what you’ve just mentioned, it sounds like you need a solution that can… Is that correct?”

3) Compromising Value Through Desperate Discounts

Offering discounts prematurely usually signals desperation and diminishes the perceived value of your offering. From the buyer’s point of view, it suggests that the product or service may not be worth its original price or that the business is struggling. This negative impression can seriously undermine trust and jeopardize long-term client relationships.

To avoid this:

Focus on building up the value of your product or service before discussing price. Articulate how your solution meets their specific needs and emphasize ROI. If a discount is necessary, frame it as a strategic choice benefiting their particular situation. For example, “If we move forward this month, I can offer a special pricing structure to help us get started.”

4) Skipping Details with Rushed Questions

Rushing through your questions can lead you to miss critical details about the prospect’s needs, resulting in inappropriate solutions or misunderstandings. It also displays a lack of thoroughness and empathy on your part as a salesperson, which can drive some prospects away.

To avoid this:

Slow down and make sure you fully explore each topic you discuss with the prospective client. Use pauses after responses to reflect on the information provided before you formulate follow-up questions. Also, it’s beneficial to prepare a list of topics to cover and remain flexible when delving deeper into details throughout the conversation.

5) Lacking Structure in Your Sales Conversation

Without a clear structure, sales conversations can become disjointed, unnecessarily lengthy, and ultimately ineffective. This lack of organization can confuse prospects as critical aspects of the solution may be overlooked — resulting in a lot of missed opportunities down the line.

To avoid this:

Develop a roadmap for your sales conversations that includes all the key points you want to address. While this helps you guarantee that all fundamental areas are covered, you should be flexible and adapt based on the flow of the conversation. If the sales discussion steers off track, try to guide the prospect back to the main topics gracefully.

4 Psychological Principles For Designing Your Sales Questions

1) Reciprocity

Reciprocity is a psychological principle that suggests people feel obliged to return favors or respond in kind when something is given to them. In sales, this principle can be leveraged to build trust and cooperation. When you offer genuine value or insights first, prospects are more likely to reciprocate with their attention, information, or even action.

Here’s how to put this into practice:

Start your sales conversations by offering something of value — which could be a useful piece of advice, a free trial, or insightful analysis relevant to the prospect’s business. Follow this with a question that invites further engagement, like “Given this information, how do you see it fitting into your current strategy?” This approach will enrich the conversation and nudge the prospect to take quicker action later on.

2) Curiosity

Curiosity drives people to seek out new information and experiences, making it a powerful tool in sales. By sparking curiosity about what the prospect can achieve with your solution, you’ll keep them engaged and more receptive to hearing more about your offers.

Here’s how to put this into practice:

Frame your questions in a way that reveals there’s more to be gained by continuing the conversation. For instance, you might say, “I’m curious to know how you handle X process currently. We’ve helped similar companies improve this by Y%, and I’d love to discuss how.” This teases potential benefits and invites the prospect to learn more about your offer.

3) Social Proof

Social proof comes in many shapes and sizes in sales, from testimonials and positive reviews to detailed case studies for similar clients. The idea is that people will conform to what others find effective, which makes this an excellent way to build trust with prospects and reassure them from the get-go.

Here’s how to put this into practice:

Integrate social proof into your questions by referencing how other successful companies, especially well-known industry leaders, have made similar decisions. For example, ask, “Would you be interested in hearing how Company X improved their revenue by adopting our solution?” This will make any potential customer interested in your solutions, pushing them further down the sales funnel.

4) Urgency

Urgency in your sales conversations compels action by suggesting that time and opportunities are limited. This psychological principle is critical because it encourages prospects to make decisions quickly, preventing delays that might cool off their interest.

Here’s how to put this into practice:

Create a sense of urgency in your sales questions without appearing pushy. Phrase your questions to highlight the immediate benefits or the risks of delay, such as “As we’re approaching the end of this quarter, starting now could ensure you see improvements by the next one. How soon would you be ready to begin seeing results?”

Sales Dialogue Dynamics: A Balance of Information and Value

One common pitfall in sales is to become so engrossed in gathering data that you forget the ultimate goal: building value.

When questions become too probing without adding value, prospects can feel like just another sales target. By doing this, you’ll risk making the conversation feel transactional, which can lead even the most qualified prospects to withdraw.

Here are three strategies for balancing information gathering with value building in your sales conversations

Begin by Identifying Key Challenges

Opening conversations by identifying pain points immediately demonstrate to prospects that your focus is on their needs and challenges. This will help position you as a problem-solver rather than just another salesperson forcing them down the pipeline.

When applying this tactic, make sure each question also shows how your services can solve those issues. This helps you gather necessary information while demonstrating the direct benefits your solutions offer.

Integrate Questions Smoothly into the Discussion

Incorporating sales questions seamlessly into the flow of conversation helps you maintain a natural and engaging dialogue with any buyer. This is important for ensuring that the exchange doesn’t feel forced or scripted — enabling prospects to play an active role in the discussion.

Aim to incorporate questions smoothly into the natural flow of the conversation based on their relevance. This strategy allows you to foster a dynamic discussion that adapts as it evolves rather than feeling like an interrogation of the prospect.

Expand on What Your Prospects Share

When you build on your prospects’ answers, you create a dialogue that feels personalized and attentive. This technique is great for gathering more detailed information while reinforcing the value of your solution as directly relevant to their expressed needs. 

Build on what your potential buyers say by asking follow-up questions that delve deeper into their initial responses. This demonstrates that you’re actively listening and care about your prospects’ challenges, enabling you to emphasize how your solutions directly address their needs.

How to Use AI to Craft Winning Sales Questions

1) CRMs

Modern Customer relationship management (CRM) systems are often equipped with AI functionalities that analyze customer data to uncover trends, preferences, and past interactions. These AI-driven insights are crucial for crafting relevant, personalized sales questions that can engage your prospects effectively.

Keep in mind that investing in AI-enhanced CRM systems requires continuous investment in sales training. Ensuring that sales teams are proficient in using these advanced tools is essential for maximizing their potential and effectiveness.

2) Sales Enablement

Sales enablement tools analyze vast amounts of sales data to suggest the most effective content, questions, and follow-up strategies tailored to different stages of the customer journey. Combine that with AI and your sales team will gain access to dynamically suggested modifications to sales scripts based on real-time customer interactions.

Beyond crafting sales questions, AI sales tools can serve as a bridge to other departments such as marketing and customer service, fostering a unified approach to customer engagement across the company.

3) AI-Driven Analytics

AI-driven analytics platforms are one of the key advantages sales representatives have in today’s market. By analyzing engagement metrics and customer responses, these tools can provide deeper insights into the effectiveness of different sales approaches.

A practical example of this would be how an AI-driven analytics tool can accurately highlight which questions are most likely to elicit positive responses and lead to conversions, thereby optimizing sales strategies for better outcomes.

What’s Next?

What makes these questions so powerful is that they open the opportunity for transparent communication. 

Don’t get bogged down in analysis paralysis. Always remember that people sell to people. Prioritize authenticity as you pursue your prospects. 

Eventually, these questions will come naturally as you take a genuine interest in helping potential clients succeed. 

As you refine your questioning techniques, remember that each stage of the sales funnel demands a unique approach tailored to guide your prospects through their buying journey. 

Whether you’re exploring their challenges, building rapport, qualifying their needs, or handling objections, the key lies in asking questions that add value and demonstrate your commitment to their success.