13 killer B2B sales questions to close more deals

by Steli Efti

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

Questions enable you to control the direction of the conversation and engage your prospect in a more relevant and powerful way.

Here are 13 questions that will help you to turn prospects into buyers.

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?

Why is this a killer question? Because it:

  1. Allows you to understand what makes them interested in your solution
  2. 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 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. 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, the objectives they want to achieve.

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

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 all of your 24 hits are nice-to-haves. You missed a must-have and all the effort you invested into the opportunity is lost.

3. 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 and manage it.

4. 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?

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 is involved in the process? If so, make sure they can implement your software smoothly and quickly. Your customers should experience the value they signed up for as quickly as possible.

5. 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 #2 (which is about understanding their must-haves, should-haves, and could-haves).

6. What's the timeline for making a decision?

When do you plan to make the purchase? Is it in a couple of days, weeks, months or years?

This sales question will help you understand the investment required to make the deal happen, as well as recognize if there is urgency and if a prospect needs more immediate attention.

You’ll be able to forecast revenues and opportunities more accurately, which in turn helps you allocated your resources and time more effectively.

7. 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?

8. 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 the last purchase was a disaster, understand why and disassociate yourself from that by explaining how you’re different.

9. 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 give you the opportunity to ask follow-up questions.

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

10. How do you see your business grow, 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 the next one or two years, how do you see our business grow, how do you see our 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.

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.

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

12. 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.

13. 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.

Bonus question contributed by Trish Bertuzzi:

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

Yeah, we promised 13, but Trish Bertuzzi from The Bridge Group shared this great question in the comments section and we decided to work it in here. The question helps you to gauge the prospect's sense of urgency.

Make these 13 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. And if you haven't done so yet—join our free sales course!

What other sales questions do you often use to move deals forward? I'd love to read your success stories in the comments!