30 Killer B2B Sales Questions to Close More Deals

30 Killer B2B Sales Questions to Close More Deals

In sales, it’s more about the questions you ask than about the answers you give. The right sales questions enable you to practice the most powerful skill in any sales conversation: listening.

Questions help you to control the direction of the conversation and engage your prospect in a more relevant and powerful way. But what are the right sales questions for your team's sales strategy? Great sales professionals know that the same types of questions apply no matter what you’re selling, although there will certainly be nuances based on your prospect’s needs.

This article includes key types of sales questions to use throughout the sales process in order to help you build rapport and close the sale. We’ll look at proven sales questions that build trust with decision-makers, follow-up questions that reinforce that you have been listening and understand the customer’s needs, and conversation triggers that indicate what question to ask during a specific phase of the sales cycle.

Let’s get started!

First: Why Open-Ended Sales Questions are Always Better Than Close-Ended Questions

Asking the right questions is critical for you and your sales team’s success, so it’s important to define the two general types of questions you’ll use during your sales calls.

Close-ended questions are questions that have a very brief answer such as “Yes”, “No”, “Red”, “Blue”, or “Monthly.” Good salespeople know that the only time to use a close-ended question is to close a deal or to confirm their understanding. For example, “Is Tuesday between 2 and 3 p.m. a good time to meet to sign the final contract?”

Open-ended sales questions are the ones salespeople should use almost all the time! You can tell a good question by the response you get. The prospect’s response will range from a sentence to a short story. For example, a sales rep selling a network security device won’t ask “Have you had many security issues?” because the answer is yes or no. They’ll instead ask, “Can you share what your top IT security needs are?” This gets the customer sharing information that will help you tailor your solution to their needs.

Sales Qualification Questions

Your best customers (and potential customers) are the ones that are worth pursuing, but how do you know if it’s a good fit? The answer is qualification questions, and they’re a critical first step in ensuring you’re not wasting your time with someone who isn’t the decision-maker, doesn’t need your product/service, or is nowhere near ready to make a buying decision.

You know when you’ve wasted time on a dead-end lead, and leaving the prospect feeling the same way could hurt future dealings.

Before your call, you should always research the prospect on social media, LinkedIn, and their company website/social channels to ensure the person you’re calling is an ideal prospect. Once that’s done, begin your conversation with the following questions.

1. How did you hear about us?

Why did you pick up the phone? Why didn’t you hang up already? I’m sure you’ve hung up on many other people who cold-called you, so why are you still on the line with me? Why did you open my email or respond to it? What exactly about my email sparked your interest?

This question both helps you understand the prospect’s thought process and understand which lead-generation tool was successful in gaining a new prospect. Learning this information will help you establish another way to connect with the lead, especially if they learned from a colleague, were referred by a current customer, or saw your brand in at a trade show or conference.

Why is this a killer sales question?

  • Allows you to understand what makes them interested in your solution
  • Reminds them why they are interested in this and why they are spending time with you

Ask this question early in the conversation. The answer will guide your approach to the conversation, tell you which angle to use when conveying the benefits of your product, and which questions to ask to keep them engaged. It’s a shortcut to gaining real insights into their wants and needs, so you have a more targeted conversation.

2. Was there a compelling event that caused you to reach out to us?

Since you reached out now, what triggered your outreach? What’s happened at your company that indicates that now is the time to look at solutions?

Trish Bertuzzi from The Bridge Group shared this great question in the comments section and we decided to work it in here.

Why is this a great sales question?

  • Gives you information about pain points the prospect is trying to overcome
  • Provides an introduction to the prospect’s problem-solving process

The question helps you to gauge the prospect's sense of urgency. Be sure to use it during your initial discovery call. People don’t randomly call for new product/service vendors on a whim, so something caused them to pick up the phone, send an email, or fill out an interest form.

3. What are your must-haves, should-haves, and could-haves?

What’s a dealbreaker? What’s a nice-to-have? What’s an absolute requirement, and what would be a nice addition?

Early on in the sales process, you qualify your prospect to understand their wants and needs, the challenges they face, and the objectives they want to achieve.

The next step is to help your prospect prioritize. Otherwise, you’ll end up with a long wishlist, without knowing which of the items on the list are of crucial importance.

Why is this a useful question for salespeople to ask?

  • Helps you align your offering with the prospect’s top priorities
  • Provides an introduction to the prospect’s problem-solving process

Separating the must-haves from the could-haves protects you against wasting a lot of time on deals that won't ever materialize. You might feel you're on track because you hit 24 out of the 27 wants and needs you elicited. But if all of your 24 hits are nice-to-haves, you may be missing a must-have that could break the deal.

4. Have you ever used a product/service like ours before? If so, what happened?

What vendors are you currently using for the products/services we offer? What do you like about their product, and what do you wish was better? Do you have other products or services that you would consider changing vendors for?

During your sales calls, you will learn the ideal customer’s current solutions, the products they use, and all about your competitors and how good (or bad) they are. You’ll be able to respond with “I hear that a lot.” or “That sounds familiar.”

Why is this a killer question in the sales process?

  • Allows you to reference pain points other customers have cited about a competitor
  • Provides an idea of transition time and expenses you should account for in price quoting
  • Allows you to showcase your ability to work with complementary softwares and services

You’ll also be able to make notes in your CRM system about current practices so that when you discuss the time frame for implementation you can refer to any data conversion or product (re)cycling.

Pro tip: Save the answers to these essential sales questions in Close with Custom Activities. These give you an easy, structured way to save the data you need and make it visible to the whole team.
Save Sales Questions in Your CRM

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5. What do you feel is a reasonable timeline to have a solution in place?

What is your anticipated launch date for new solutions? What is your implementation timeframe?

You need to know whether or not it’s possible to provide your product within the prospect’s ideal timeframe. Knowing their timeline and the capabilities of your organization, you’ll be able to spot trouble early on and set reasonable expectations.

Why is this a killer question?

  • Anticipate feasibility and discuss rush fees up-front

You’ll also be able to discuss any timeline concerns with your implementation team early on.

6. Is anyone else that we need to involve in the discussion?

Are you the sole decision-maker here or do we need to involve additional people? Should we loop your IT director, training manager, or any other colleagues who will be part of the roll-out?

This is the last question in our section on qualifying questions, and it’s an important one. Unless you’re talking to the company’s CEO, there’s always someone at the company who can overrule your contact. Get an idea of the key figures at the company from their company LinkedIn page, corporate website, or social media channels.

Why is this a killer sales question?

This question helps plan your conversations with other contacts at the prospect’s company so you can build rapport.

Open-Ended Sales Questions to Build Rapport

Many great business relationships are built on just that—relationships. The most effective way to build relationships with your prospects is to engage them in conversation.

Allowing your prospects to speak and be listened to is the foundation of rapport building, often because the customer may not be actively listened to by people outside their company that understand what is going on in their field. You provide that consultative, friendly ear by asking the right questions early in the relationship. These questions can help!

7. I saw the [big company update] on your social media. How’s that going?

What are your thoughts on the pending acquisition of Competitor X? What are you looking forward to most if they end up hiring the new engineers I saw advertised on your company’s social media page?

You must do your homework before meeting with a prospect. Successful salespeople have done enough research to know as much about a company as can be known from its website, social media channels (especially LinkedIn), and marketplace reputation.

Why is this a killer sales question?

  • Provides your prospect with the understanding that you’ve done your research
Killer Sales Questions to Build Rapport

This question builds early rapport so you can connect with your prospect over current happenings at their company.

8. What do you think about the latest [industry-specific trend]?

What do you think your business practices will look like after [this trend] becomes the new big thing? How are you implementing the new changes?

This is a great question for moving the conversation along when it gets stuck. It refreshes everyone’s line of thinking about the present and future trends, so it is very helpful when someone gets stuck on a “way we’ve always done it” line of dialogue.

Why is this a killer question?

  • Refocuses conversation on present/future and not the past
  • Builds trust by showing sales rep is knowledgeable about industry trends

This question helps build trust because it shows you’re not just some sales rep who doesn’t understand the industry, you’re well-informed and have industry expertise.

9. Many of our clients tell us [this]. How do you think that applies to you?

How have you worked to solve the pain points that our other clients have overcome with our solution? They tell us their biggest challenge is [this]. What are some of yours?

You want to assure your prospective clients that you have experience addressing their biggest pain points with ease in a low-stress, highly consultative way. This also allows you to update your notes with insights based on their response.

Why is this a killer question?

  • Puts prospects at ease while reinforcing your expertise

10. What about you? What kind of goals do you have right now?

Now that we’ve covered your company, what will you personally be celebrating in six months? Sounds like a lot of exciting changes but also a lot of stress. Any big plans or personal goals over the coming months to keep sane?

Building rapport isn’t just about connecting on business; it’s about building a personal connection with your contact. In most cases, you won’t become best pals with a lead, but you also need to establish a little more than a business-only conversation or you risk being inauthentic. You may even reach out to the contact on LinkedIn to connect more directly.

Why is this an insightful sales question?

  • Establishes a more personal connection and builds trust with your contact

By building a personal connection, you can also create a foundation for ongoing outreach if the contact moves to another company.

Want more qualification questions? Get our mega list of B2B qualification questions:

Discovery Questions to Gather Insight During the Sales Process

Now that you’ve built some rapport with the prospect, using open-ended discovery questions helps you assemble all of the information you need to construct a killer presentation and proposal. Using the following questions, paint a picture for your client of how the next steps in the sales process go together.

11. How has your business changed (or adapted) since a specific event?

COVID-19 really did change everything. How did your business adapt during the peak of the pandemic? How has it changed since then? How have you adapted since Microsoft stopped supporting Windows 8.1? With gas prices the way they are, how have your shipping and transit practices changed?

Here, we’re talking about a specific event that is not company-created, but rather a widely known consideration for the marketplace or the specific industry.

Why is this a killer question?

  • Positions you as knowledgeable in your industry
  • Gives you important clues about how the business will adapt to change during a potential new product/service introduction.

12. What's your decision-making process like?

How are you making buying decisions in your organization? How are you going to evaluate whether we are the right solution or not?

This question helps you understand how they arrive at a decision. If you understand the process, you can influence it, move it forward, control it, and manage it. You can also compare the prospect’s process to other customer’s experiences.

Why is this a killer question?

  • Allows you to anticipate prospect needs

13. Who are all the stakeholders involved in this deal?

Not just from now until the buying decision, but also after the purchase. Who are all the stakeholders involved and affected by this deal from now to the time of closing and five years beyond, when you’re already a customer?

Sales Questions to Discover Stakeholders

You want to know all the stakeholders because if you don’t know who the players are, you can’t play the game.

It’s not just about closing the deal; it’s also about turning every closed deal into a success story.

Is the prospect’s IT department involved in the process? Will the legal department need to approve contracts? Who has control over finances? Who are the end-users of your product within the company? Knowing these things before that last sprint will help you prepare so the deal goes smoothly over the finish line and beyond.

Why is this a killer question?

  • Involves more contacts at the prospect’s company, allowing you to build more connections

This also allows you to identify, through LinkedIn and company website research, potential areas you can include in your sales pitch or talk tracks.

14. What’s the company’s biggest goal for the next six months?

If all goes well, what will you be celebrating in six months? What strategic goal in the next six months that you’re working on? In six months, what goals do you hope to achieve?

Frequently, you won’t be talking to someone who is always forward-focused. Day-to-day issues and short-term goals often cause people to lose sight of the long-term strategy. By asking open-ended sales questions like this one, you move them out of their short-term thinking and set them up to discuss the long-term benefits of your product/service.

Why is this a killer question?

  • Refocuses the conversation on long-term benefits/goals

This also provides you with more context about the company and possible future sales opportunities.

15. How do you see your business growing and your needs changing over the next one or two years?

Let’s assume you’re making a buying decision now and become our customer. For over this year and next year, how do you see your business grow, and how do you see your needs change?

This question allows you to anticipate what it’s going to take to grow this relationship. Selling doesn’t end when a prospect turns into a customer. Closing the deal is just the beginning of the next stage in the sales process: retention.

Sales Questions About Growth

Why is this a killer question?

  • Allows you to set up reminders for check-ins based on customer-provided triggers
  • Allows you to show your genuine excitement for their growth

Ask yourself: how can I double, triple or quadruple the business with this customer within the next 12 months? You want to know if there are huge opportunities around the corner with this prospect so you can make sure to work with them on making it happen.

16. What’s holding you back from achieving your goals right now?

As we move through this process, what resources could we provide to help you achieve your goals? What roadblocks do you keep running into as you work to achieve your goals?

Asking your prospect questions about roadblocks is a great way to get them thinking about how their current solution is not meeting their needs, and how yours can. It allows you to describe and demonstrate how your product/service can alleviate their pain points.

Why is this a good sales question?

  • Provides a list of pain points you can address to help move prospects to customers

17. What are the pathways to tear down or bypass those barriers?

When we worked with another client who had similar challenges, we were able to help by doing this. Do you think that would work for you? What does that look like moving forward?

After you address how your solution can solve some of the issues the prospect identified, you’ll want to act as a consultant as they think through how your product/service will solve all their biggest challenges. Summarize these steps in writing and create a brief plan that they can self-monitor. They’ll thank you and see even more added value in your company.

Why is this a killer question?

  • Creates a deliverable for the client and positions you as an expert consultant.

18. What have you tried before?

We know that finding the right solution can be a lot of trial and error. What kinds of things have you tried before and how have they worked? What about your processes needs fine-tuning to make sure things always run smoothly?

When people call us to discuss our CRM solution, they’ve often tried self-hosted solutions, competitor’s products, and even a wide array of poorly organized excel files. For your industry, we imagine the same. Even a company providing paper products sometimes finds itself sending someone to the local warehouse store when toilet paper supplies run low. What process does your product/service optimize?

Why is this a killer question?

  • Helps establish that your way is the better way
  • Provides an opportunity to show savings of time and resources

Sales Questions to Prove Your Product’s Capability

At this point in the sales process, you’re in a good place. Your prospect is qualified, you’ve gathered enough basic information to understand their problems and how your solution can fit in, and you’ve developed a working relationship that allows your prospect to trust what you have to say. Now’s the time to investigate any doubts your prospect may have about your product or service and prove your product as the ideal solution.

19. What are other products/solutions you’re currently using that our software has to integrate with?

Which other software solutions will our software have to play together with? Will our product need to integrate with other things you’re using today?

You want to understand their stack and the environment in which your solution will have to operate.

All too often, sales reps invest weeks or months into a deal, only to discover there’s an impossible-to-fulfill, must-have integration. All the time and effort invested into the deal are lost; this is why it’s crucial to ask this question early on in the sales process.

Even at Close, this occasionally happened. Fortunately, we've now got plenty of ready-made integrations to make Close play nice with most cloud platforms our customers want, and there's always the Close API for custom solutions.

Why is this a killer question?

  • Provides a list for you/your implementation team to review when quoting a price
  • Allows you to learn about other solutions that yours can either replace or complement—another benefit to share with a prospect!

20. What kind of support/service/help do you need to become insanely successful?

Do you want us to train every person on your team? Do you want us to show up at your office? Do you want us to create a step-by-step guide especially for your users? Do you want us to create a specific customization for your company? What kind of relationship would you want to have with us after you become a customer?

Some prospects want to just use the software and be left alone. Some prospects will want a more involved and collaborative relationship.

Both of these are fine; just know their expectations so that you can ensure they get the experience they want.

Why is this a killer question?

  • Informs your sales process about whether or not to add training or support to your sales pitch
Sales Questions to Inform Your Sales Pitch

21. Who else are you comparing us with?

What is the current solution you’re using to address this challenge or achieve this objective? Why are you considering a change? What sparked your interest in us? Who else are you evaluating? What are all the available solutions you’re considering?

Every prospect has alternatives to choose from if they don’t buy your solution. And it’s not just competing vendors.

Often the alternative they’re choosing is either developing an in-house solution or deciding not to change anything at all.

If you know the options your prospect is considering, you can understand the playing field and know how to position yourself most favorably. You can set the frame for the deal so that you emerge as the most viable option.

This knowledge becomes even more powerful if you have the answers to question #X (which is about understanding their must-haves, should-haves, and could-haves).

Why is this a killer question?

  • Gives you the ability to point out why your solution is better
  • If the sale doesn’t go through (it happens!) you’ll be able to track what competitor you lost the bid to so you can become more knowledgeable about how to compete in the future.

22. How are you currently using [2-3 innovative product tools]?

Most of our clients use a, b, and c. What kind of solutions are you using? How do solutions like a, b, or c integrate into your process?

Many prospects will be using multiple vendors to do what your product can in one package. This is an opportunity to point that out and discuss conversion strategy.

It is also a way for you to describe how your solution will integrate with existing systems.

In the case that your system does not integrate flawlessly with what they are using, it’s a feature request you can relay to your development team.

Why is this a useful question?

  • Provides an example of how your product adds value
  • Shows that you have worked with customers who have similar system conversion needs

23. What other features are you looking for in your final solution?

If you had a magic wand and could wave it and the perfect system was in place today, what features would it have and why?

This helps your client brainstorm, sometimes for the first time, all of their ideal features. You can have a list of your product’s features ready to check off all the ways your solution is the perfect fit for their most critical needs.

Why is this a helpful sales question?

  • Provides a list of features to focus on in your sales pitch

24. What resources do you have or need to oversee successful implementation and maintenance?

What resources are available to assist you with this change, including people?

As you advance through the sales process, responses to open-ended sales questions will become more list-based or shorter. If a customer provides well-assembled list answers, you know that you’ve asked great questions and they’re putting effort into getting you the information you need to develop a killer final proposal.

Why is this a killer question?

  • Identifies that the prospect has a good (or bad) team behind them
  • Provides context for including additional implementation staff and resources in your final proposal costs

Questions to Close the Deal

Now you have arrived at the final part of this stage of the sale. Questions in this area will serve one purpose: Identify if the prospect is ready to sign on the dotted line or what last pieces they need to become ready.

You will notice that the answers to questions become shorter, and you may even start to ask some strategic close-ended questions to get definitive answers from your lead.

25. What will it take to win your business?

What is it going to take for your company to become a customer of ours? What do I have to do to win your business? We’ve now had our first conversation about working together, let me ask you: how are we doing? After everything you’ve learned during this conversation, how do you feel about us? How interested are you?

This question will help you gauge their interest and allow you to ask follow-up questions.

If they're positive, ask what they're most excited about. If they seem uncertain, ask what their main concerns are so you have a chance to address them.

Why is this a killer question?

  • Provides you with information about what is most important about your proposal (It’s not always price)
  • Gauges interest and qualifies the likelihood you can find a good solution for their problem
Sales Questions to Close the Deal

26. When was the last time you made a purchasing decision for a solution like ours?

When was the last time your organization bought something similar to our solution? What was the decision-making process back then? Why did you decide to buy that specific solution? Was it a success or failure?

This question helps you to use the past to close a deal in the present.

If they’ve recently bought something—great! It indicates that they’re an active buyer.

If the last time they bought something was 20 years ago—not so good. That’s a red flag. It might be very hard to get these people to a buying decision.

If the last time they bought a solution was a success, great! Associate yourself with that. If not, distance yourself from that.

Why is this a killer sales question?

  • Provides final qualification as a buyer

27. What's your budget?

What’s the investment you’re looking to make in this area?

Many times a prospect won’t give you a concrete number; don’t get hung up on it. The purpose of this question, apart from knowing their budget, is to start negotiating the price. But remember: talk value before price.

If they're going to get $10, $100, or $1,000 for every dollar they invest into your solution, are they going to make the purchase? Or are they operating under financial constraints that would make a purchase prohibitive above a certain price point, even if they could clearly see that it offers them a 10X or higher return on investment?

Are they in it to get the best or the cheapest solution?

Why is this a killer question?

  • Determine if your pricing is out of their range and adjust sales strategy or offering
  • Identify if your product/service is over or underpriced compared to the marketplace

28. Is there anything that could stop this deal from happening?

Is there anything that could threaten our partnership or get in the way of this contract being signed? Anything you can think of that would prevent us from moving forward in the next few days?

When a prospect has stated that they’ll soon go ahead and buy, your first instinct may be to jump up and high-five everyone on your team. But if you’ve been in sales for long enough, you know that a deal isn’t closed until the purchase is made. Asking this question can help you navigate roadblocks and close the deal sooner.

Why is this a killer question?

  • Allows you to overcome barriers in the buying process by sharing information to alleviate doubts
  • Identifies industrial or market conditions that may be a threat to other areas of your business

29. Is there anything we’ve talked about that you need more information or clarification on?

What haven’t we covered that you need to know to make your purchasing decision?

Ideally, the client will respond, “Nothing, I have everything I need.” and you can send over the proposed contract and set a timeline for follow-up. If they still have questions, it’s your opportunity to answer them.

Why is this a killer question?

  • Ensures thoroughness and eliminates roadblocks
  • Clears up any questions the prospect may have about the buying process or any area of your sales pitch that they may have overlooked

30. What do you need from me to get the onboarding process started?

Looks like our solution addresses all your pain points. If that’s correct, can we look at terms? Are we on the right track here?

This question is asking for permission to submit the final proposal. You might also ask this question as a close-ended question such as, “Do you have everything you need to make a purchasing decision?” This provides you with the assurance that you’ve done a thorough job and it’s now in the buyer’s court to decide.

Why is this a fantastic sales question?

  • Allows you to advance in the sales cycle process in a customer-focused way
  • Provides more opportunities for clarifying timeframe, metrics, and decision-makers in a consultative way

Make these 30 B2B sales questions part of your repertoire and practice working them into your conversations. They’ll help you to move prospects through the buying stages faster, manage your sales pipeline more effectively, and ultimately close more deals.