Strategic Discovery Questions to Ask Every Prospect

BY Jessica Helinski
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It’s important to ask strategic discovery questions to uncover a prospect’s true needs, goals and pain points. Only with this knowledge can you effectively position your solution and present value. Unfortunately, sellers struggle with discovery.

Why strategic discovery questions matter

SalesFuel found that nearly a quarter of sellers report that discovery questions are a top weakness. It’s vital that sellers bridge this gap. Otherwise, they won’t be able to optimize their sales efforts because they don’t have essential details. 

RAIN Group’s Mary Flaherty recognizes the importance of asking the right questions to get in-​depth knowledge. 

[This] allows sellers to design solutions that are tailored to fit the unique circumstances of each buyer,” she writes. 

The right questions should start before the meeting

It’s a common misconception that you start digging for information during that first discovery meeting. But why wait? Flaherty suggests that sellers don’t waste time waiting for the meeting. 

Consider reaching out to the lead via email for some pre-​meeting engagement. Include just a few basic questions that will kickstart the process. 

According to Flaherty, asking in advance can:

  • Often provide more answers than you would be able to get during a call.
  • Shorten the sales cycle.
  • Encourage rapport early, thanks to pre-​meeting engagement. 
  • Inspire deep thinking by allowing them to answer on their own time. 

Mix up your questions

Once you’re in the actual discovery meeting, make sure to ask a variety of strategic discovery questions. SalesFuel has also discussed the importance of asking open-​ended questions. But you can tap into a wider variety of this type for even more insight. 

Kick off the conversation by asking some general, broad open-​ended questions. This is an effective way to warm things up, according to Sendoso

A broad, open-​ended sales question helps salespeople to get prospects to open up and begin talking.”

These questions invite more than a “yes” or “no” response but don’t dive directly into heavy business talk. You can ask if anything new has happened since you last spoke. Or inquire about how the current quarter/​month is going for their business.

Once you’ve encouraged some dialogue, it’s time to go deeper. This is when you can start asking more hard-​hitting open questions. 

There are a variety of these questions to choose from; take a look at these suggestions. And be sure to consider asking probing open-​ended questions as well. 

Probing questions are designed to encourage deep thought about a specific topic,” explains Calum Grey

[They] ask for more detail on a particular matter.”

Then, as the prospect opens up, you can expand on their responses by asking closed questions. These "yes" or "no" sales questions can challenge them to consider things differently. 

Asking these questions, in this order, allows you to get the prospect to open up first and then explain their needs. Then, you can help them expand on those needs beyond what they’ve identified.

Don’t forget “why”

Flaherty advises sellers to always include one of the most basic yet powerful questions: “Why?” Specifically, she suggests a technique that involves asking “why” at least five times throughout the meeting. 

This enables you to “collaborate with buyers to uncover the root cause of what is driving their needs,” she writes.

Then, once you’ve brought that issue to light, you can demonstrate clearly how your solution can help.

Before your next meeting, integrate these strategic discovery questions into your plan. You’ll find that you and the prospect will uncover valuable insights together. You’ll have the opportunity to position yourself and your solution as the best choice. 

And for more guidance on preparing for your calls, take a look at these tips.

Photo by Christina Morillo