How to Ask Probing Sales Questions Carefully to Avoid Losing Business Leads

Samir Sampat

Probing questions are an important part of the lead generation and qualification process. These questions help you better understand exactly what it is that your lead is looking for, or what problem they may be struggling with. This, of course, is just one of the many sales techniques that your team will need to hone, but it’s an important one.

In the guide below, we’ll take a look at probing questions, including what they are, how they can help you, and more. Plus, we’ll even take a look at what probing sales questions should be doing for you and how to use them to make decisions easier for your leads.

What are probing questions?

Probing questions are uniquely created to encourage detailed thought on a specific topic. It helps people consider the deeper facets, in this case, of the buying journey, to make the right conversion move. Ultimately, you’re trying to use these questions to get prospects to reveal information that will help you make a sale or get the conversion.

You may get information that the prospect didn’t disclose right away. For example, you might have a prospect with a secondary pain point that you can solve with a total conversion in your sales pipeline. You wouldn’t know that, though, if you didn’t take the time to ask probing questions. You also have to make sure that you’re asking the right questions.

Examples of probing questions

·  What problem can we solve?

·  What is your budget like?

·  Why do you think that’s so? (In regard to a statement the buyer might make)

·  What will help you decide on closing?

·  Why isn’t your current product/service working?

The first question allows you to quickly understand what the issues at hand are and what the prospect is hoping to gain from resolving them. You can’t just accept the first answer and leave it at that, though. You have to keep probing. Ask who, what, where, when, why, how, etc. The right questions will lead you right to the perfect path to turn prospects into customers.

You might even find that there’s more than one issue at hand and that you’re being charged with solving. It gives you a chance to build rapport, showing the prospect that you care. Asking about their budget also helps you assume the buying process for them. Instead of saying, “If you work with us…” you can say, “How much can you afford to spend with us?” This makes them think ahead and put themselves in the position of a buyer or customer and not just a lead.

It's also important to find out why they’re looking for a new solution—what’s wrong with the one they have or had? Has there ever been a solution or is this going to be the first? If you’re becoming a new solution for someone, they might be trying to make a certain improvement on their existing solution. If this is their first need for your products or services, you need to make sure that you make a great impression. And if you’re replacing the competition, you need to make an even better one.

How to make sure you’re asking the right questions

There’s more to probing questions than just inquiring with your customer about their needs or problems. It’s about getting as much information as you can about your prospect so that you can create the best possible closing pitch to seal the deal. When you are using probing sales questions, you’ll want them to do things like:

·  Help determine the competition

·  Single out a decision-maker

·  Pinpoint the frustration or pain points

·  Identify issues and problems from the start

·  Determine priorities and urgency

·  Qualify prospects

·  Fast-track your close

·  Clarify what the customer expects

·  Help you understand the buying process

·  Identify previous challenges

These questions will also help you gauge how ready your prospects are for change and whether it’s time for your business to step in and close the sale with a much more targeted perspective of your audience than before.

The more you know…

When it comes to prospecting and qualifying leads, the more you know, the better off you will be. You’ll have much better odds of successfully converting prospects and delivering the exact right solution for their pain points, no matter what those might be. The more helpful you are by digging deep with probing questions, the more likely you are to become the prospect’s first choice for the solution to their problems. It’s a cycle, and it’s worth having all of your sales reps learn to manage.

It's all too easy to lose leads in today’s instant gratification world. The Internet gives people short attention spans and an overwhelming number of options. While the latter seems like a perk, it’s actually a detriment. You see, as humans, we struggle with choice. Thus, the more options we have, the more likely we are to struggle with making any moves at all. If you use probing questions properly, you can deter people’s fear of too many options and help them pinpoint exactly what they want and need from your business.

Or, you can partner with the team at for outbound sales support and more

Whether you need a little help with your outreach campaigns or you just want to have the systems in place to field all the new leads once they start coming in, we’ve got your back. The virtual receptionists at can be your solution for 24/7 phone answering, live website chat support, and even Facebook and SMS message answering. That way, no matter how busy you are, you’ll never miss an opportunity.

Our team of agents can also assist with lead qualification and scheduling, giving you more time to focus on the customers in front of you while the leads are taken care of elsewhere. Plus, we’ll create a custom strategy to manage all of it, no matter how big or small your needs may be.

To learn more, schedule a consultation to discuss how the 24/7 virtual receptionists at can deliver solutions for your outbound sales and more. You can also reach us at or (650) 727-6484.

Samir Sampat

Samir Sampat is a Marketing and Events Associate with He has experience working with businesses of all sizes focusing on marketing, communications, and business development.

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