Want to Close Bigger Deals? Ask Better Discovery Call Questions

What is the meaning of life? 

Are aliens out there?

Did the chicken or the egg come first? 

There are a lot of difficult-to-answer questions out there – but fortunately, as sales professionals, it’s our job to do the asking, not answering. 

Nailing discovery call questions – the questions you ask during the first meaningful conversation between you and your prospect – is an essential part of becoming a good sales pro. Your goal here is to understand the buyer, not pitch the product. 

Ask the right questions, and you’ll get to the bottom of your buyer’s motivations – which, in turn, will allow you to position your solution in the best way possible. Remember: the best deals are closed with great discovery, not perfect demos. 

If this all sounds a bit overwhelming, we’ve got you. Keep reading, and you’ll learn all about essential discovery call questions (hint: good ones start with intel on their industry, size, and growth signals, which you can find with Surfe’s Company Search API), how to ask them, and how to turn your insights into impact:

• Discovery Isn’t Qualification – It’s Curiosity
• Discovery Call Questions That Go Deeper
• 7 Discovery Call Questions That Actually Work
• Getting Permission to Sell: The MSS Approach
• Discovery Beyond the First Call: Post-Sale and Partnerships
• Discovery Call Do’s and Don’ts

By the time you’ve finished reading, you’ll be a pro at asking the kinds of questions that go beyond surface-level qualification. A true philosopher of sales, if you will 😉 Let’s get started. 

Discovery Isn’t Qualification – It’s Curiosity

Too many reps treat discovery calls like a checklist:

• Number of seats
• Budget
• Timeline 

And so on and so forth.

This approach is…fine, but it’s a little perfunctory. If you’re too focused on ticking boxes, you’re going to lose the essential element of a good discovery call: curiosity. 

A discovery call is your shot at understanding the human (and the business) behind the calendar invite – a well-run one should build trust, uncover urgency, and discover what’s really going on. 

And the secret to getting it right? Discovery call questions. 

Discovery Call Questions That Go Deeper

Let’s dig into the three different types of discovery questions. Ideally, you want to use a mixture of all three on each call. 

The Bucket Question

First up: the bucket question. The goal here is to bring up the core issue the buyer is trying to solve. 

For example: “What’s the biggest thing slowing you down right now?”

This kind of question surfaces the problem at the top of their mental inbox. It sets the tone for the rest of the conversation and gives you a clear starting point for uncovering value.

The “Why” Question

The “Why” question is all about uncovering urgency and emotional drivers. 

For example: “Why is now the right time to solve this?” or “Why hasn’t your current approach worked?”

“Why” questions add depth and help you understand what’s motivating the prospect to act (or not act) right now.

The Gap Question

Last but not least: the Gap question. These reveal hidden inefficiencies the buyer may not be aware of.

For example: “Is there anything in your current workflow that just feels harder than it should?”

Help your buyer spot the cracks in their current processes, and you’re helping them discover their pain. And that, our friends, is the difference between a box-checking sales rep and a sales rep that gets a call back. 

7 Discovery Call Questions That Actually Work

Ok, so now you know the three different types of discovery call questions. Now, let’s dig deeper: we’re going to look at some discovery call questions that will take your call from good to great. 

“What’s the biggest challenge your team is facing right now?”

This question opens the door to real pain points – which is often far more revealing than asking about goals. Think about it: a painkiller is more effective, and more necessary, than a vitamin, right? 

“Why is this a priority now?”

Here, you’re getting to the urgency – or lack of it – behind the problem. This is going to help you understand timing (when’s best for you to reach out? How quickly are they looking to move? Where should they be on your priority list?) and context. Spoiler: if your prospect can’t tell you why something is a priority, it probably isn’t one.  

“What’s holding you back from solving this today?”

This question might seem like a tricky one to ask up front – after all, you’re asking them to tell you why things might not work out – but it is vital. If you know what blockers are coming up (internal, budget-related, or emotional, for example) you can make sure you’re well-prepared to handle them when they arrive. 

“If this issue continues, what’s at risk?”

Here, you’re creating urgency by inviting the prospect to consider what could go wrong if they don’t do anything. If you articulate the risk, you might come across as pushy or salesy – by getting the prospect to do it, you’re making the momentum come from them.

“What have you tried already – and why didn’t it work?”

This question helps you position your solution as a smarter next step to what they’ve already tried. It’s also a great way of making sure you really can offer the service they need – and finding out what you need to keep an eye on during the upcoming sales process and onboarding stage. 

“What does success look like six months from now?”

Reframing the conversation around outcomes is super smart: it helps align your pitch with what they actually care about, and gives an impression of progress before you’ve really begun. 

“Is there anything in your current process that just feels harder than it should?”

This question is a great way of subtly probing for gaps – gaps that your prospect may not have even noticed themselves. Remember, the more intel you have, the better. And that includes the stuff your prospect hasn’t mentioned.

If you’ve been reading carefully (which we’re sure you have!) you’ll notice that all of these questions spark conversation (no yes/no answers here), build trust, help the buyer reflect on their current state, and guide the conversation toward value, not qualification. 

Getting Permission to Sell: The MSS Approach

Once you’ve uncovered a real problem – and the buyer actually feels it, too – you’re standing at a pivotal moment in the conversation. But before you launch into a pitch deck or rattle off features, wait!

A high-impact discovery call isn’t about closing. It’s about getting permission to move forward in a way that feels natural for both sides. This is where your discovery call questions have already done the heavy lifting. You’ve surfaced the pain, understood the context, and now it’s time to connect the dots.

Enter: the MSS (Might Make Sense) approach.

It’s simple, low-pressure, and lands like a soft recommendation instead of a sales pitch. Here’s what to say: 

“So, this might make sense… You’re dealing with [problem], which is leading to [consequence], and stopping you from [desired outcome]. Our solution was built to solve exactly that.”

Why It Works:

• It shows the buyer you’ve actually listened
• It frames your solution as relevant, not random
• It makes next steps feel like a mutual decision, rather than a closing tactic
  

The MSS transition keeps the discovery call collaborative – which is exactly what a discovery call is supposed to achieve in the first place, rather than a hard sell. That shift in tone can be the difference between a polite “Thanks, but no thanks” and a booked follow-up call with real intent. 

Discovery Beyond the First Call: Post-Sale and Partnerships

The best revenue teams know that real discovery doesn’t stop after the first call, or even after the sale. If your business wants to build long-term relationships (which we’ll assume is the case) discovery needs to evolve. 

Customer Success: Staying Curious After the Close

Once the deal’s signed, it’s tempting to assume you know what success looks like. The contract’s done, the onboarding checklist is out, and everyone’s happy. Right? 

Well, in the short term – yes. In the long term, however, your team needs to be careful to steer clear of making assumptions. 

Customer Success Managers who keep discovering post-sale can unlock way more value. By continuing to ask thoughtful, open-ended questions, they can:

• Uncover *real* success metrics (“launch fast” vs. “boost ARR by Q2”)
• Spot adoption blockers before they become churn risks
• Show they’re still invested – long after the paperwork’s done

And the questions don’t need to be complex, either. Simple, curious prompts go a long way: “What’s holding your team back right now?”, “Why is that outcome important to you?”, or “What would a win look like in the next 30 days?” are all excellent starting points. 

Wonder something along the lines of “What is a discovery call actually meant to accomplish post-sales?” We’ll tell you: continuous alignment. The more you understand your customer’s evolving needs, the easier it is to drive retention, expansion, and advocacy. 

Partnerships: Discovery for the Long Haul

Discovery is a big part of the partnerships role, too. When a partnership hits autopilot, it’s usually because nobody’s asking the right questions anymore. Keep the dialogue active by exploring:

• What customers are struggling with right now
• What outcomes matter most this quarter
• Why prospects might choose a competitor instead

Treat every check-in like a mini discovery session, and you’ll keep the relationship sharp, mutual goals front and center, and the partnership ready to bring in that sweet, sweet revenue – not just surface-level alignment. 

Treat every check-in like a mini discovery session. It keeps the relationship sharp, mutual goals front and center, and the partnership positioned for revenue – not just surface-level alignment.

Discovery Call Do’s and Don’ts

Let’s be honest: most discovery calls go off the rails because reps are either over-prepared (read: scripted to death) or under-prepared (read: winging it). 

Here’s a quick gut check on what works – and what quietly kills your success.

Do:

• Lead with curiosity, not an agenda
• Ask open-ended, thoughtful discovery call questions
• Listen way more than you talk

Don’t:

• Rely on a rigid script
• Jump into pitch mode the second they mention a pain point
• Accept surface-level answers without digging deeper

Quick Pre-Call Checklist

Before your next discovery call, take 60 seconds to run through these questions:

• Do I understand the company and the world they’re operating in?
• Do I know who I’m speaking to – and what actually matters to them?
• Am I prepared to ask questions that reveal pain, not just gather facts?
• If things go well, do I have a transition in mind (like MSS) to keep momentum going?

Keep these questions in mind, and you’ll be best placed to set yourself up for success – on the call, and later down the line. 

Let’s Wrap It Up: Ask Better Questions, Close Bigger Deals

Look at you, you sales philosopher!

You’re just so good at answering all the right questions – you know, the ones that throw up the really, really important answers and drive trust, urgency, and closed deals. 

You’re asking better questions, having better conversations, and experiencing better outcomes as a result. Next up – the chicken, or the egg?

Questions About Discovery Call Questions 

What Is A Discovery Call In Sales?

A discovery call is the first real conversation between you and a potential buyer – where you’re not selling, you’re learning. Think of it as the sales version of a first date: you’re getting to know each other, figuring out if there’s a fit, and uncovering what the other person really wants (and needs). You do not want to be pitching your product: instead, it’s about asking smart, open-ended questions to understand pain points, goals, and blockers. If done right, discovery calls build trust and set the foundation for a deal that actually solves a problem – rather than one that just ticks a quota box.

What Are The Best Discovery Call Questions To Ask?

The best discovery call questions are the ones that spark real conversation. They go deeper than “What’s your budget?” and aim to uncover motivation, urgency, and roadblocks. A few high-impact examples include:

• “What’s the biggest challenge your team is facing right now?”
• “Why is this a priority now?”
• “What have you tried already – and why didn’t it work?” 

These types of questions help you move beyond surface-level info and get to the good stuff: context, pain, and opportunity. 

How Do You Structure A Great Discovery Call?

A great discovery call is about having a clear framework and staying curious. Start with research: know the company, the person, and what might matter to them. Then, open the conversation with trust-building questions (no pitch yet). Use a mix of “Bucket,” “Why,” and “Gap” questions to uncover pain, urgency, and hidden blockers. If it sounds like a good fit, use a permission-based transition like the MSS approach: “This might make sense…” That way, you’re moving the conversation forward naturally, without sounding pushy or robotic.

Why Are Discovery Call Questions Important In Sales?

Discovery call questions are where the magic happens. They show your prospect you’re not just there to push your product – you’re genuinely curious about their world. The right questions help you uncover pain points, understand context, and identify whether your solution actually fits. Plus, they give you ammo to tailor your pitch in a way that resonates. Ask the right questions, and you’re solving real problems – and that’s what leads to bigger, better deals (and way fewer ghosted follow-ups).

How Can I Improve My Discovery Calls?

Want better discovery calls? Start by ditching the script and leading with curiosity. Do your homework before the call so you’re not asking things Google could tell you. Ask open-ended questions that uncover pain and urgency, like “What’s holding you back from solving this today?” or “What does success look like six months from now?” Most importantly, listen more than you talk. And if the call goes well, have a smooth transition ready (like the MSS framework) so you’re not awkwardly leaping into pitch mode.