Create winning pitches and sell more. We’ve put together the best probing questions for sales to help you build rapport, solve problems, and shape an irresistible offer.

A winning sales pitch convinces a lead that you’ll provide real solutions to their business problems. There’s an art to crafting conversations to help you connect with your leads, engage them in conversation, and genuinely listen to their concerns. Half the battle is knowing the right questions to deliver the information you need to address the problems and close the deal.

Here are seven types of probing questions for sales that always deliver:

1. Spin-Selling Questions

SPIN is a handy acronym that outlines a question-asking strategy to help you lead a conversation and pinpoint a solution faster. It stands for Situation, Problem, Implication, Need-Payoff, and you can use it by asking a series of targeted probing questions for sales prospects who may be a tough sell. Here is an example of how it works:

  • (Situation) How long have you been using this janitorial service for your office?
  • (Problem) Do you feel like you are paying a lot for what they provide?
  • (Implication) If you weren’t spending so much to keep the space clean, could you afford additional staff or some upgraded equipment?
  • (Needs-Payoff) How would more flexibility in your budget help you do business if you could get the same or better service for a lower monthly cost?

Read more about SPIN selling questions here.

2. Broad Open-Ended Questions

Broad open-ended questions are the ultimate warm-up for connecting with your leads. Open-ended questions allow you to learn more about a person, including their values, before narrowing the conversation down to details. It’s tremendously helpful in engaging your leads instead of leaving them with the feeling that they’ve been “talked at.” Here are some ways to start out broad:

  • How is business going for you?
  • Can you tell me a bit about your background?
  • What are some of your pressing concerns?

Read more about broad open-ended questions here.

3. Targeted Open-Ended Questions

Once you’ve connected more broadly, use targeted open-ended questions to narrow the topics down and bring in more probing questions for sales specifics. Get the information you need to craft a more personal pitch. Try these three questions to start focusing on the problems:

  • What is your most urgent priority right now?
  • What is your timeline to meet those goals?
  • What could we do to remove some of the obstacles you are encountering?

Read more about targeted open-ended questions here.


lead-managerlead-managerAfter you gather targeted information from your best leads, schedule a free demo of our sales and marketing follow-up software and automate your follow-up effortlessly. 


4. Closing Questions

Use closing questions to advance to the next step after you’ve engaged them in a conversation and thanked them for their time and input. These are action-oriented targeted questions phrased in a way that supports your pitch and makes it easy for the lead to say yes and give your business an opportunity to show them more. Here are some ways to craft a good closing question:

  • Ask for their opinion: “Thanks for taking the time to discuss your concerns. In your opinion, do our services address the problems you are having? What more could we do to help?”
  • Ask for a chance: “It seems like you are in a tough spot and need to make some changes to address these concerns. It’s clear to me that our solutions could help, how would you feel about giving us a chance to see if we could meet your goals more effectively?”
  • Assign a date: “Based on what we’ve discussed, I’d be happy to get you a proposal this afternoon detailing some suggestions for how to address your business needs. Are you available Monday morning to get started?”

Read more about closing questions here.

5. Close-Ended Questions

Close-ended questions are meant to provide you with very specific, straightforward pieces of information. Use questions like these when you are looking for quantitative data, yes or no answers and specific action requests:

  • Were you completely satisfied with your last vendor?
  • Are the features we offer helpful to you?
  • Are you ready to set up some time to meet so that we can get you started?

Read more about close-ended questions here.

6. Trial Close Questions

Trial close questions are for when you feel like the lead is warmed up but you don’t want to push or rush them into the next step too fast. It’s helpful to test the water to see if they are ready to commit to moving forward or if more engagement is necessary, before pushing to make the sale. You can figure out how best to proceed by asking trial close questions like these:

  • Does it sound like our services would be a good match for your business, so far?
  • Now that we’ve outlined our features, do you feel like they adequately address your concerns?
  • What are the next steps you are looking for at this time?

Read more about trial close questions here.

7. Discovery Questions

Discovery questions are incredibly useful for sales calls and higher-priced sales fields like real estate and insurance. Think of these as a fact-finding mission or the first step in prospecting leads and cultivating them by getting to know your potential customers and how they define their immediate needs and desires. Here are examples of what to ask, right out of the gate, to gather the right kind of information to move forward:

  • What is your biggest challenge right at this moment?
  • What do you look for in a (company like ours)?
  • If you hire us, how will you define success?

Read more about discovery questions here.

With lots of practice, you’ll find that each of these types of probing questions for sales will become integrated into your natural conversational style. Soon, every lead conversation will be working to deliver the information you need to craft a winning pitch and close the sale.


lead-managerlead-managerAfter you gather targeted information from your best leads, schedule a free demo of our sales and marketing follow-up software and automate your follow-up effortlessly. 


Do you have any types of probing questions for sales prospects you would add to this? Share your tips in the comments.