How to Ask Discovery and Probing Questions to Win More Deals 🔎

In the first of our three-post series, we are walking through the fundamentals of a sales discovery call. In our first post, we looked at three things you should add to your pre-call research checklist, what makes pre-call research effective, and how it can help you have a value-driven conversation with your prospect to improve the buyer experience. 

In this second post, we'll explore how to ask discovery and probing questions to qualify a lead and uncover buyer pain.

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Discovery and Probing Questions

There are several different types of questions that the seller will ask during the sales process, including discovery questions and probing questions.

What exactly is the difference?

Discovery questions will help you qualify the lead and learn about the initiative to identify if he or she will be a good fit for your product or service. 

Probing questions uncover the business pain the prospect is experiencing.

Let’s discuss both.

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Probing Questions

Two central tenets of sales include asking questions to uncover pain that the prospect did not fully realize when they first started looking for a solution, and to become a trusted advisor through the sales process. Those two concepts align with popular B2B sales methodologies, The Challenger Sale and SPIN Selling, respectively. 

We’ll go into details on these in a future post, but let's take a look at a quick example customer interaction below:

Here is what 95% of reps do:

Prospect: “Does your product support a Salesforce integration?”
Seller: “Yes. Let me tell you about my company…” (dives into pitch)

This is a missed opportunity!

Instead, try asking probing questions to uncover the true business pain:

Prospect: “Does your product support a Salesforce integration?”
Seller: “Yes, why are you looking for a Salesforce integration?”
Prospect: “Our deal desk approval process is an issue. Our sales team works out of Salesforce, but our legal team works out of their own proprietary system.” 
Seller: “That makes sense. I’m curious, why do you say this process is an issue?”
Prospect: “Well, a small percent of our deals slip into the next quarter because of the manual and error prone process.”
Seller: “Understood, we’ve heard similar feedback from [insert customer story]. Beyond just being a manual process, there sounds like real business implications. How many deals does your sales team have per quarter and what is your average selling price (ASP)?”
Prospect: “about 50 deals per quarter and $100k ASP”

Sometimes just asking why makes all of the difference. In both situations, your product can help the prospect, however, in the latter scenario, you can tie your solution to real business pain.

You’ll notice I inserted a customer story into the line of questioning. This accomplishes a couple things:

• Turns the questioning into a more natural conversation
• Provides validation to the prospect that you are familiar with their pain points, which in turn, will get them to open up more
  

By asking questions and uncovering the business pain impacting your prospect’s organization, the conversation just turned from a feature discussion to a value-driven discussion through the use of probing questions. This will be helpful to drive momentum in the sales process, create a compelling event, and overcome any inertia that may arise.
It is challenging for a seller to balance so much information on the call: 

• Company research 
• Product information 
• Persona interests
• Competitors

...and more.

I’d encourage you to write down your favorite probing questions you want to ask prior to the customer meeting or use in-meeting enablement software to assist.

Qualification Questions

BANT, and more recently, MEDDIC, are qualification frameworks used by organizations in order to qualify leads during the sales process. For sales reps and sales leaders, it provides a more data driven approach to forecasting deals vs. relying on how a rep may ‘feel’ about the deal happening.

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We’ll get into a future detailed post on both of these frameworks, but at a high level, you’ll want to ask questions that:

Identify Pain & Metrics:

• What goals are they trying to accomplish? Why is this important?
• Understand how the pain is impacting their business. Ideally, you can uncover business metrics to help evaluate ROI of the purchase (i.e. 10% of deals slip into next quarter because of this missing feature)
• What are they doing today to try to solve this pain? How is this problem impacting their business?

Decision Criteria:

• What are the technical requirements they are evaluating against? How are they measuring success?

Decision Process:

• The last time they purchased software, what was the process? How long did it take?
• Have they evaluated solutions before to solve this? What happened the last time they evaluated a solution?

Champion:

• Is the person you are working with able to help you navigate the customers organization? Have they purchased software before? Are they able to bring in executive stakeholders to meet with your management team?

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Budget, Economic Buyer (or authority), Timeline

By qualifying pain and engaging with the right level stakeholder, you’ll have a better idea if there is a budget allocated for this project, if there is enough of a compelling event to get the deal done, and who the decision maker is.

Two other ways I try to qualify budget and timeline, without directly asking, include:

• Asking how the initiative got started
• Inferring the prospect’s appetite for spend based on what they currently use in their tech stack

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Asking how the initiative got started:

Seller: “Is this initiative something you’ve started to look at on your own or is there a management mandate around solving this issue? 

If the evaluation was started by the prospect on their own, unless they are the decision maker (i.e. Director, VP, or above), you’ll want to work with them to get higher in the account and engage more stakeholders. If he or she blocks you from doing this, they are likely not the right champion for you. Unless you can find alternate stakeholders to help you navigate the organization and processes, this may not be a qualified opportunity. 

If the initiative involves Objectives and Key Results (OKRs) or Key Performance Indicators (KPIs), with a mandate coming down for senior leadership, you can be sure there is a budget allocated for the project. This is also valuable information to help drive urgency in the deal.

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Inferring the prospect’s technology spend by what they currently have in their tech stack

Another approach I use to qualify budget is by asking questions that allow me to infer their appetite for purchasing enterprise software:

Seller: “Can you tell me about some of the tools in your tech stack?”

If someone tells you they are using Salesforce, Netsuite, and Marketo it is a very different conversation than if they are using Pipedrive, Quickbooks, and Mailchimp.

In the former, you know they are used to investing in enterprise software. In the latter, I’d be concerned about budgetary sensitivities. 

Internalize your discovery questions, write them down as a reminder, and/or use in-meeting enablement software to help prompt you with the right questions at the right time.

Ever hang up and forget to ask a critical question to the prospect? 

Me neither, but I can imagine how frustrating it would feel!

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Become the trusted advisor

Outside of questions you ask, prospects will be asking you questions on the discovery call that are business, pricing, technical, legal, security, etc. related. Typically there will be a Notion, Google Slide, PowerPoint, and/or Sharepoint doc that has prospect FAQ’s that are maintained by Sales Leadership, Enablement, and/or Product Marketing. 

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Commit this Q&A to memory. According to Salesforce, 58% of pipeline stalls because reps are unable to add value in their customer conversations.

It is always better to tell the buyer you will follow-up with a response, then to make something up. Alternatively, there are in-meeting enablement tools that can surface this type of information live on the call.

By showing an understanding of your customers business, as well as your own product and market that you operate in, you are building trust with your prospect that will help you through the rest of the sales process.

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Until next time...

Thank you for taking the time to read this post on how to ask discovery and probing questions – I hope you found it valuable!

Next up, we’ll cover the importance of communicating and following up on action items/next steps with your prospect.

Lastly, if you ever want to talk about any of this, or all things go-to-market, in more detail, send me a LinkedIn message and/or you can find me on Twitter.

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- Dave

Co-Founder & Chief Business Officer @Aircover

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