46 Sales Discovery Questions That Help You Win Deals

How many deals are you losing in discovery? 

If you don’t take the time to dig deeper into your prospect’s challenges, key drivers, and company to understand how you can help them achieve their goals, then our guess would be, a lot. 

Without being on the ball in discovery, you can have the world’s greatest product but lose your sale to an AE with better questions.

But in a rush to get to the demo, companies often skip this step altogether, which wastes precious time and resources and leads to prospects dropping out of the sales funnel because they were never truly a good fit.

Too many AEs make prospects sit through a call only to give them a vanilla demo that doesn’t specifically address their problems and pains. 

We sell to salespeople, so we know all about how challenging discovery is.

Sales discovery questions are targeted questions that help you better understand your prospect, their challenges, and whether they’re a good fit for your solution.

Asking great questions should be at the center of your sales discovery checklist.  

During discovery and sales prospecting, there’s a lot you need to find out. 

So how should you structure your sales discovery questions?

Your discovery questions should be open-ended to get your prospects talking. There’s little to discover about your prospect if they’re only answering ‘yes’ or ‘no’ questions. 

Matching sales discovery questions to the appropriate stage of the buyer’s journey helps build rapport and confidence in you and your solution, so you can move steadily toward closing a deal. 

By understanding your prospect and their pain points by asking the right questions, you’re building trust and forging a lasting relationship. 

There’s lots to find out, but you need to make sure your prospect doesn’t feel interrogated.

Source: UserGems' Krysten Conner, LinkedIn

Choose from the following questions to help guide discovery—but don’t ask all of them. 

And remember never to just read from a script. Use a balanced, flexible approach to discovery. Prepare and rehearse your questions, but leave enough room for the natural ebb and flow of the call. 

Let’s explore some effective discovery questions to help you run a better sales discovery process. 

Sales discovery is a crucial step in understanding how you can bring value to your prospects. 

Being a successful salesperson means you genuinely care about what your prospects are dealing with. You’re there to help, and you’re endlessly curious about the ways you can help them best.

Preparing your discovery call questions helps you gather all the information you need to get aligned, excluding information you should’ve already gathered during the sales qualification stage.  

If you’re using Mixmax, information gained from qualification will already be in your CRM and up to date, thanks to the two-way Mixmax-CRM activity sync. 

We’ve listed several questions below for different stages in the discovery process. These will help guide your discovery to feel natural but make sure you get straight to what you need to know.

We're also including an interview with a sales influencer, Marcus A. Chan, who talks about his POWERFUL methodology when it comes to discovery:

Pro tip: To build rapport with your prospects, listen more than you talk (aka active listening)—we suggest an 80-20 ratio. And when you do talk, make sure it’s about them, not you.

Sales discovery questions to ask for situational context 

Your prospects want to feel like you really get them.

By asking the right questions, you can show them they’re more than a buyer persona. Treat them as individuals with unique problems, to find out the specifics of their current situation and where it hurts. 

Your main goal should be to uncover a potential fit between your solution and your prospect’s priorities. 

This is your chance to empathize with them, validate their circumstances, and verify your previous assumptions and information you gathered in qualification. 

Ask questions like: 

These questions help define what’s lacking in their current situation and give you valuable information you can use to address their pain. 

Sales discovery questions to ask for dormant pain

The fact that your prospect showed up to the call means there’s something bugging them, even if they don’t know exactly what. 

Pain in this sense can mean anything from a minor annoyance to a key source of frustration for your prospect. 

It’s your job to find out where it hurts, draw attention to it, and look for ways your solution can help. 

Your questions should be focused on them, not you. The questions below help you fully dive into their dormant pain and bring it to the surface. 

Ask questions like: 

These questions tell you about how they’re currently managing things—and most importantly, how it’s working out for them. That gives you a chance to see where your solution can bring value (maybe it saves them X hours on Y process they do every day). 

Sales discovery questions to ask for active pain

Once you’ve unearthed your prospect’s pain points, it’s important to dig deeper and have them verbally address their pain, so they’re fully aware of their desire to solve the problem.

According to Kyle Parrish, VP of Sales at Mixmax, “Great salespeople are problem finders as well as problem solvers. Without pain, there is no sale. Prospects do not buy ‘features’ of the product, they buy a solution to a problem that they have. If you can't associate your product or service to solving the pain of your customer, you leave it up to them to make the association—and that’s not a risk worth taking.” 

By addressing their pain, you can tailor your solution to better address their needs. If prospects aren’t even aware of their problem, they’re not yet ready to look for a solution. 

Ask questions like: 

These questions help pinpoint exactly what their pain is—and where it comes from—which helps you drive urgency for your prospect. 

Sales discovery questions to ask to measure pain implications

Your prospect’s pain points need to be quantified to fully understand the implications of that pain. 

Ask questions to put their pain in perspective, specifically looking to understand the price they pay in dealing with their challenges. 

You should also make sure to ask about their bigger plans and goals for the year…and how their pain points are blocking them. 

Ask questions like: 

Sales discovery questions to ask for understanding the buying process

Understanding your prospect’s current buying process is the first step in gently directing them towards a better one.

Fully grasping their processes (their decision-making, buying, contracts, etc.) is very important—it’s the best way to shed light on how the process would potentially look like with your company and solution.

Buying process questions should communicate your genuine interest in their processes to understand potential opportunities where your solution could add value.

Ask questions like: 

These questions show you how quickly your prospects move through product adoption, and what to expect if they move forward with your solution. 

Include some budget-specific questions, too. 

Try asking:

These questions give you a sense of what their budget is, what they’re willing to pay, and whether they’re getting their money’s worth with the solution they’re using right now.

All of this background is gold for any AE looking to show prospects that your solution offers better cost-to-value. 

If you find out your prospect doesn’t have a budget, don’t stop there. Go deeper to understand whether it’s possible to create one, and what that would look like. 

Ask questions like:

Sales discovery questions to ask for the evaluation stage

Once you’re on top of your prospect’s obstacles, processes, and desired outcomes, what’s next? 

It’s time to ask questions to evaluate whether your prospect is fully confident that your solution will solve their problem. And if they’re not, you need to find out why not.

Questions include: 

Sales discovery questions to ask for the decision stage 

During this stage of discovery, you need to find out the best next steps to take and understand who’s responsible for giving the go-ahead. 

It’s super important to ask:

Sales discovery questions to wrap up 

When wrapping up the call, ask specific, direct questions to see if your prospect is interested in moving forward with your demo. 

If they’re showing signs of hesitation, address it. Asking them upfront can help build trust because it shows you’re not ‘wounded’ by their reluctance to move forward. This sends the message you’re not wrapped up in your own ego: you’re committed to taking the time to understand them and put their needs first. 

Try asking these questions: 

Mixmax makes the discovery process a breeze. Use the in-email dialer and resource-sharing features to do all your discovery from one place.

This lets you focus 100% on your conversation and questions, without worrying about updating and jumping between different tabs. 

Mixmax makes in-email calling super easy

Deals are won and lost in discovery. 

You don’t want to lose another deal—or give your brand a bad rap—because of poor discovery. 

Solid sales discovery questions can kick off a strong discovery process. But it’s not just about asking the right things: it’s about going outside your comfort zone to put the buyer at the center of all of your questions and concerns. 

The best reps understand prospects’ problems and stay curious to find out how they can help.

They know you can’t skip this crucial step: you can’t pitch until you understand a prospect’s pain and you can’t understand a prospect’s pain until you’ve asked them.

Running a successful sales discovery process is a lot simpler when you're getting help from a reliable sales engagement platform.

Mixmax saves you time and headspace by automating repetitive tasks, keeping you on track, and asking the right questions, with email sequences and rules.

By asking the right questions, you've understood the prospect and gotten them intrigued enough to set up another meeting.

If you’re using Mixmax, you can also send an email with your availability and a one-click meeting-booking link to make scheduling your demo easy for everyone (no back & forth).  

Don’t miss out on discovery by asking generic questions. Stay curious about how you can bring value, and use this guide and Mixmax to really focus on the call and get the most out of discovery.