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50 Valuable Sales Prospecting Questions

50 Valuable Sales Prospecting Questions To Get the Conversation Going

The era of the talky, pushy sales professional is over.

There have been plenty of discussions about the changing roles of salespeople in the era of technologically-enhanced selling. Buyers report wanting a far different sales experience from the stereotypical fast-talking, high-pressure experience.

Contrary to popular belief, here’s something top producers have practiced for ages: Listening.

These high-performing sales professionals know that if you talk openly and genuinely with your prospect, they’ll tell you exactly what they want and need. In fact, they’ll willingly offer up the information. And one of the best ways to get to the heart of the matter quickly is by asking the right questions.

Below are 45+ of those right questions that are sure to open up discussions, reveal needs and motivators, build trust, and ultimately close deals.

Open-ended vs. Close-ended Sales Prospecting Questions

How you ask a question is just as important as what you ask. Therefore, a good mix of open- vs. closed-ended questions can give you a wide selection of data from which to plan your approach. What’s the difference?

  • Open-ended: A question that cannot be addressed with a binary (e.g., “yes” or “no”) answer. The question is answered in such a way that your respondent has to elaborate. Ex: “What was your favorite feature of our competitor’s program or service?”
  • Closed-ended: A question that can be answered in a single word, or with a binary answer. Ex: “Do you like our product or service?”

Open-ended answers are more fact-finding and qualitative in nature. They’re meant to perpetuate the conversation, get the prospect thinking about near-term negotiations, or otherwise move the conversation toward a closing. That said, there’s nothing to say you can’t ask closed questions, but be reasonably sure of the answers you’ll get when using them. Nothing shuts down a constructive conversation like a firm “No” at the wrong time.

5 Best Practices for Asking Sales Prospecting Questions

There’s a way to ask questions to get the best results. Like with any new relationship, peppering someone with rapid-fire questions is a sure way to stop the conversation in its tracks.

Sales Prospecting Best Practice #1

Build Rapport: Having important conversations is all about getting comfortable, and here’s where your small talk skills can really come through. Use some of the opening questions listed below to start the call with a casual tone, and build a friendly rapport with your prospect. People are more apt to do business with people they like, and those personal interactions can give your prospect the right impression.

Sales Prospecting Best Practice #2

Set the Agenda: If you’ve asked the right questions in advance of your discovery call, you’ll have the info you need to frame the call. Setting a clear agenda and expected topics for a meeting can help your prospect understand what you’re offering, and set up the call for success. It also provides a framework to keep the conversation to a reasonable time frame and enables the sales rep to have control of the conversation.

Sales Prospecting Best Practice #3

Keep The Balance: You have to give a little to get a little. In a healthy, engaging conversation, each participant should be contributing their fair share. In a sales call? Top reps let their prospects do a bit more of the talking (some sources suggest a 46-to-54 talk-to-listen ratio). This balance should space the questions organically throughout the conversation, and let them weave naturally into the talks.

Sales Prospecting Best Practice #4

Get Interested: “I’d love to hear more about that!” is a great way to send the conversation in a helpful direction, while making your prospect the star of the show. These open-ended, deliver questions allow your prospect to stretch their professional legs and dive deeper into a topic they are well-versed in, while potentially offering valuable clues that can aid in the discovery and evaluation process.

Sales Prospecting Best Practice #5

Close the Deal: Once you’ve educated and evaluated your prospect—asking questions that ensure what you’re offering will be a great solution you can provide—you can move into closing territory. This is where your closing finesse comes into play. Layout the next steps in the process, get your customer’s buy-in, and move to close (for simpler transactions), or set another meeting with a wider net of stakeholders to move the sale to completion. If you’ve done all the right things in your process, you’ll have confidence in the closing process based on what the prospect says and does during the closing phase.

Types of Sales Prospecting Questions

Opening Questions

Fostering a relationship requires a personal touch. No one wants to talk to someone who just wants to cut to the chase. When talking with a prospect, be sure to warm up with some questions that get them talking about everyone’s favorite subject (themselves, of course!).

  • How is your day going?
  • How is the family/pet doing?
  • What are your plans for the upcoming holiday/How was your [holiday]?
  • What do you have planned for the weekend?
  • Tell me a bit about your background in [industry]?
  • I noticed we have [contact] as a mutual connection. How do you know them?
  • How has business been since last we talked?
  • Are you heading to any conferences or tradeshows this year?

Bonus: “How is your [personalized gift item] working for you? I hope you’re enjoying it!”

Information Gathering Questions

To understand where your prospect is headed, you need to know where they are at the moment. Asking information-gathering questions gives you a great perspective on what services they’re currently using or challenges they might be facing in their business. Some questions that might be useful for gathering good information include:

  • When was the last time you purchased this product/service/technology?
  • What provider are you working with now? 
  • What is going well for you with your current provider? 
  • When did you first notice you had a changing business need?
  • Is there anyone else who should be included in our discussion? 
  • What other providers or solutions are you evaluating? What are you seeing?
  • What is the most important aspect of a provider for you? 
  • What are you hearing from your influencers regarding this problem? 

Objective & Goal-Setting Questions

Understanding the plans and goals your prospect has in mind is an excellent way to respond to their needs—not just immediately but over the long haul. For this reason, objective and goal-setting questions are a great way to understand your potential customer’s long-term plans and needs.

  • Why are you embarking on this purchasing process?
  • What would you like to see accomplished at the end of this process?
  • What are your stake-holders hopes for this process? 
  • What are your next quarter and next-year goals? 
  • Can you effectively meet those goals in the current solution or situation? 
  • How much easier would it be to accomplish your goal with a better solution in place? 
  • What goals could you set with a more effective solution in place? 

Business Pain Point Questions

Finding the thorn in your prospect’s side is the quickest way to help them see how a solution can improve their daily lives. Pain points aren’t always obvious. Sometimes, for example, a solution might be working; however, if it’s cumbersome or requires workarounds, it can slow down sales reps, causing goals to suffer. Digging into the effects can be a great motivator to change.

  • What isn’t working out with your current solution? What issues are you having?
  • What blocking issues is your current solution creating to your plans? 
  • What is the biggest hassle for you in daily operations? 
  • Has the lack of a solution affected your employee turnover?
  • Has your customer attrition rate suffered because of the issue? 
  • How has revenue reacted to this problem? 
  • What revenue projections could you effectively reach with a better solution in place?

Future-Oriented Questions

At some point in the conversation, it’s time to get your prospect thinking about next steps. This future-looking set of questions can reveal the urgency and motivation your potential customer is experiencing, without the bluntness (and risk) of a binary, “Are you ready to move forward?”

  • What does success look like for your business and our work together?
  • What resources do you currently have in place to implement the solution? 
  • What resources (not already accessible) will you need to tee up? 
  • What is your timeline for getting a solution in place?
  • What is your contract and capital expenditure process?
  • How soon would a solution need to be in place to meet your upcoming deadlines or goals?

Qualifying Sales Questions

Budget and qualification questions are one of the final steps before moving into closing territory. They subtly signal the need to talk about the money aspect of the deal while ironing out pricing objections before they become an issue. They also ensure that your contact is either able to move on the decision or motivate the necessary stakeholders to do so (with your assistance).

  • Have you established a budget for this project?
  • Is there anything I have missed in demonstrating the value of what I’m proposing?
  • What is your budgeting process for similar projects? 
  • What stakeholders will need to sign off on this expenditure?
  • Do you feel that our solution will address all of the issues you’re currently facing? 
  • Do you feel the need for another meeting to provide information to any interested parties? 
  • Is there anything I can provide to you for discussions with other parties? 

Closing Questions

  • What’s your timeline for making a purchase decision?
  • To get a solution in place within your time-frame, we need to have a contract in place by [date]. Is this achievable?
  • If all the criteria outlined have been met, how comfortable would you be to proceed?
  • Are there any questions that I haven’t already covered?
  • What information can I provide your finance team in anticipation of moving forward?

Armed with these best practices and questions, you’ll be on your way to discovery calls that yield the best possible results while creating strong relationships with your future customers. If you’d like to learn more about using direct mail to make those connections even stronger, we invite you to a demo of our versatile, powerful Sending Platform.

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Peter Tarrant, Account Based Marketer, Tipalti

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