Salespeople can ask 1,000 questions on a discovery call, but only a handful actually create URGENCY.

And urgency is what gets buyers to act fast. 

Focusing on potential losses (pain points) — of revenue, mindshare, marketshare, leads, etc. — is the best way to drive urgency in any deal. 

I’ve coached hundreds of successful sales reps — they all focus on building trust by asking the right questions to understand pain and create urgency. 

Use the 39 sales discovery call questions below to uncover your prospect’s pain points so you can focus on how it hurts their business. 

Then follow-up with a vision to the future state and create a smooth path to a closed deal.

These timeless principles will guarantee you deliver a great discovery call. 

Business pain point questions

In the first stage, you’ll uncover the real challenge your buyer faces, using discovery call questions. 

Later on, you’ll use this info to frame your product as their perfect solution.

That’s why it’s important to get total clarity on your prospect’s pain points.

Here are a dozen open-ended questions to get you there:

1. What challenges do you face with your current solution that you would regret if not solved six months from now

This question goes beyond the prospect’s needs and immediately taps into their sense of potential loss. 

The buyer pictures how bad things will be if they stick with the status quo (i.e., life without the right solution).

This is undoubtedly one of the best qualifying questions you can ask. 

2. Why would you regret not solving that six months from now?

Having them articulate the answer is far better than you spelling it out for them.

They’ll believe it if they say it themselves.

3. Help me understand the biggest challenges you face when it comes to [X].

Solve these challenges and they’ll give you a hero cape (right after signing).

4. How satisfied are you with [PAIN AREA YOUR CURRENT SOLUTION SOLVES]? How top of mind is that?

Now you’re gauging their sense of urgency around this issue.

5. How highly does [PROBLEM] rank on your priority slide?

If this problem is a top priority (especially for multiple stakeholders), you are likely to accelerate the buying process by asking this question. 

If it’s a low priority, focus on another problem your product solves.

6. Just to confirm… is this “THE” challenge we should be discussing? Or are there others that are more top of mind for you?

This ensures you are asking the right questions to ensure your prospect’s pain point is indeed a top priority before you build an entire deal strategy around the wrong issue.

7. If you could wave a magic wand and solve anything when it comes to [PAIN AREA] in your day-to-day, what would it be?

This question validates what you’ve already heard … or reveals any hidden issues that haven’t yet come to the surface.

Either way, it’s up there in the roster of best discovery questions you can ask your prospect. 

8. [FOR OUTBOUND DISCOVERY CALLS] I’m sure you get dozens of cold calls and emails each day. What made you take this first call?

Have they heard about your product? 

Have they seen a virtual product demo somewhere? 

Are they dissatisfied with the other potential solutions they’ve looked into? 

Find out.

9. I want to be sure I’m clear about [CHALLENGE THEY’RE TALKING ABOUT]. Can you tell me more about it?

If you make assumptions, you could end up targeting the wrong business pain points.

This is an excellent follow-up question to ensure you are focused on solving the right problem. 

10. Can you give me an example?

Use the examples they provide later in the purchasing process (when you begin to map your new solution 1:1 to their challenges.) 

11. How long has this been happening? How often does this happen?

This allows you to start calculating the true cost of this issue to your buyer.

You can show them what it has previously cost and what it will cost them in the future… unless they consider a new solution.

12. What have you tried in terms of solving it? How did that work out?

This is one of the best questions you can ask during the sales discovery process, because it will help you differentiate your solution from what they’ve tried previously.

Related: Try our discovery call planner template to crush your next discovery call. 

Negative impact questions

13. Earlier I asked what challenges you were facing that would derail you. Can you help me understand how they would derail you?

If their answer doesn’t surprise you, the problem and its consequences are likely straightforward.

If it does surprise you, it means there’s another problem lurking that you haven’t uncovered, or that you need to reframe what’s happening and the consequences.

14. Can you walk me through the ripple effects [CHALLENGE] is having on the rest of your business?

Are they aware of how far their problem stretches? This open-ended question helps you understand if the problem is affecting other stakeholders, which can give you some extra leverage throughout the B2B sales process. 

15. How is this challenge impacting the business as a whole?

This is one of the most underrated sales discovery call questions because it can uncover the wider business problem — opening a can of worms you never knew existed. 

Decision makers care deeply about these issues. So pay attention.

16. Who else does this challenge impact [FUNCTION, PERSON] and how?

Use the answer to multi-thread or consider potential champions across the company.

The more widespread the cost to the company, the better positioned you are to frame the risk of not having your solution.

Pro tip: Utilize LinkedIn to connect and engage with potential champions you have learned about during the discovery process. 

17. How much would you estimate this challenge has cost your team/the business?

Get a sense of what they think the problem costs them. 

Eventually, you’ll show them that it costs way more than they think.

Quantifying the impact of the problem is one of the best ways to accelerate the sales cycle. 

18. Mind if I ask an awkward question? What kind of ripple effect is this having on YOU?

They’ll brace for something truly awkward…

… and be pleasantly surprised that (FINALLY!) someone is asking about them.

19. What’s driving you to solve this issue now rather than later?

Understanding their context helps you tailor a new solution to their situation.

(Plus, it never hurts to reinforce any urgency they already feel.)

20. How is this challenge affecting your [INSERT A SPECIFIC IMPLICATION THIS PROBLEM AREA CREATES]?

Shine a light on the full scope of damage their problem creates. 

You may even reveal an issue they hadn’t connected back to this pain point.

21. What are the downsides when it comes to…

This is one of those sales discovery questions that gives you insight into their decision making process — it helps you understand how they weigh the pros and cons of switching to a new solution. 

22. What effect does that have on…

Again, test this problem’s reach.

You can ask about potential issues related to their business performance metrics and KPIs, their CRM and tech stack, and anything pertaining to their current process. 

Does it wreak more havoc than they thought? If yes, you are one step closer to a closed deal.

23. How often does that cause…

This is another way of asking sales discovery questions that will help you calculate the cost of the problem now and in the future.

24. How often does that lead to…

Same thing here. 

You’ll be able to get a better sense of the financial scope of their problem.

(These last two discovery call questions also help you test for issues that have remained hidden to date.)

25. What does that result in?

Are they focused on the financial costs? Or something else?

Their answers to these sales questions says a lot about how they think about the problem.

Solution questions

At this point, you might be tempted to jump into pitch mode and start blabbering about how your product solves your potential customer’s pain.

Plenty of sales professionals make a HUGE mistake at this stage:

They go into sales mode before getting the buyer to visualize an ideal solution.

Get them to visualize the perfect solution. Then frame your product to fit their vision.

26. To what extent is it important for you and the business to solve [CHALLENGE]? How would you prioritize it among your other priorities?

It may be a business pain, but is truly a top priority … or even in their budget?

Ask the right discovery call questions to find out.

27. What do you think you need in order to solve this challenge? How do you see that benefitting you?

Let them tell you exactly what they need. 

It puts them in the frame of mind that they can’t solve this problem without you.

28. Have you thought about [INSERT YOUR UNIQUE PRODUCT CAPABILITY HERE]? To what extent do you think that would help?

The answer to this question tells you how your differentiator lands. 

Adjust accordingly or proceed as planned.

29. What advantages do you envision gaining from the desired capabilities you just mentioned?

Lean heavily on their most desired outcomes (future state) during your demo/sales pitch.

30. What are some of the ways you see [VALUE YOUR PRODUCT DELIVERS] benefitting you?

Now they’re envisioning your product as their solution!

Keep going.

31. What business outcome would move the needle? How much would that be worth to you?

Again, you’re getting them to visualize the successful future they want NEED.

You’re also preparing yourself to objection handle any pushback that may arise later in the sales process — especially pertaining to pricing. 

32. Mind if I ask an awkward question? Why is that meaningful to you?

Same as before: They’ll be relieved that this isn't actually awkward. 

It’s about them! This is a key part of the buyer’s journey — getting to the emotional core of what they want.

You’ve already tapped into the logical side of their brain with concrete problems and financial costs.

Now invoke their emotions.

Purchase decision (buying process) questions

If you’ve made it this far — you’ve worked past any disqualifying events, uncovered true pain and quantified the business impact of the problem. 

This is the last round of sales discovery questions — aimed at mapping a mutually agreed-upon path to closing.

The final stretch of the B2B sales process is about clarity and managing expectations to avoid any unforeseen roadblocks that could ruin the deal. 

33. What’s changed since we last talked? (If anything). 

If you don’t ask, you won’t know about major events that require a revised deal strategy.

This includes events like budget cuts, the need for a specific integration, or facing a new decision maker, etc.

34. Can you walk me through the steps you and your company need to take to make a confident yes/no decision on this?

Salespeople must understand the entire purchasing process and every detail involved.

Without this, you may jump the gun on a specific step and hurt your chances of a closed deal.

35. Who are the people that will be involved in each of those steps? How is each person involved? Can you tell me about each person’s decision criteria?

This qualifying question helps all stakeholders align on the correct objectives and buying process before you proceed.

36. How are you thinking about funding this project?

This is a polite way to ask about their budget, and to help you prepare for any pricing related objections. 

Your buyer is less likely to balk at this line of questioning than being asked directly about their budget.

37. What circumstances need to be met for us to execute a commercial agreement by [DATE]?

This is how you get tacit agreement for your deal.

If you meet the parameters they set, it’s harder for them to back away from the deal.

38. What would derail us from getting things done from here?

This is a subtle way to ask if they know about circumstances they might not have been keen to mention so far (a difficult personality, a decision maker who may be looking to exit, etc.). 

If that something exists, find out now.

39. Is there any reason for us not to move forward with this now?

If they have a reason, address it.

If they don’t, congratulations! They’re now implicated in your plan for moving forward.

Asking The Right Sales Discovery Questions Matters

These 39 discovery call questions will take you places.

Want to go even further? Sign up for the pclub.io sass discovery master class!

It’s an entire course on how great SaaS sellers “create urgency from thin air” and sell in an economic meltdown.

Learn the exact five-step discovery system used to train the number one sales team at Gong on selling through an economic meltdown.

Remember: sales prospecting is a key part of building a fat sales pipeline, but it means nothing if you can’t advance opportunities down the sales funnel. 

Master the art of sales discovery and use this set of discovery call questions as a template for success.