5 Problem-Centric Discovery Questions (That Will Stop Customers in Their Tracks)
When it comes to sales discovery, reps are often trained to ask basic, surface-level questions about the customer’s needs.
“What type of solution are you looking for?”
“Why now?”
“What made you decide to look at us?”
The issue with these questions is that they fail to provide a sense of depth and insight into arguably the most important motivation behind the customer’s decision to even look at solutions; their problems!
In the past, I’ve spoken about engaging customers by leading with heavy doses of problem-centric (vs. product-centric) messaging. But that narrative should extend into your discovery motion too!
Here are five powerful, problem-centric, show-stopping discovery questions to uncover the hidden motivations and decision-making dynamics that typical questions miss.
1. “What Problem Are You Trying to Solve?”
Why it works: It shifts the conversation from solutions to challenges.
Most sales reps start with product or process-focused questions like “What are you doing today?” or “What are you looking for in a solution?” But the truth is customers don’t wake up thinking about products or processes. It’s problems and challenges that keep them up at night!
This question forces buyers to push beyond the superficial and articulate the demons they’re wrestling with in their own words. It also helps you understand how well they grasp their own challenges. Are they clear on the root issue? Are they describing symptoms rather than the actual problem? Is the problem they’re talking about too operational or low-level?
How to use it effectively:
- If they give you an answer that’s too basic (i.e. “We’re trying to automate process ABC”) just keep asking “Why is that important?” until you get to a critical and strategic business problem
- Follow up with the next question, “How do you know?” to uncover whether they’re making assumptions or working with real data.
- Bonus: I’ve covered 3 ways you can use this question in the initial discovery, a second meeting, and even as an objection-handling tactic
2. “How Do You Know You Have That Problem?”
Why it works: Uncovering the pathway by which the problem was diagnosed helps you validate how reasonable their assessment is.
Your customer may believe they have a problem but that intuition may be based more on a gut instinct, a small data set, or flawed rationale. For example, clients often come to me saying their reps are bad at deal negotiations. And they might justify their assessment by citing the big discounts their reps are giving to drag deals over the finish line. However, examining their sales motion earlier in the funnel often reveals that reps struggle with a lack of conviction and an inability to differentiate their solution in a crowded market, causing buyers to see them as a commodity.
This question forces them to examine their assumptions and validate the root cause of their problems.
How to use it effectively:
- Ask for specifics: “What metrics or feedback led you to this conclusion?”
- If they give you some gold nuggets, run with them and continue your discovery!
- If you feel their assessment is off, offer a differential diagnosis for the root cause of their problem based on your experience with similar customers.
Related video: What’s the “Pain & Pitch”? (and why you should stop doing it!)
3. “Why Do You Think This Problem Hasn’t Been Solved Yet?”
Why it works: It uncovers roadblocks that have prevented action in the past.
Sometimes, a problem persists not because no solutions exist, but because something—budget constraints, internal disagreements, shifting priorities, lack of urgency—keeps it from being addressed. This question forces the customer to reflect on the barriers they’ve faced and gives you insight into potential obstacles you’ll need to navigate (especially as you look to accurately forecast the opportunity).
As a bonus, the “why do you think…” portion of the question invites the customer to share their opinion on the issue (not just the facts) which is precisely the type of questions buyers love answering the most!
How to use it effectively:
- If the blocker is internal resistance, explore what’s driving the hesitation and how they’ve tried to address it
- If the issue is budget (or priority – because investment often flows to the most strategic problems), ask: “What would make leadership see this as a priority?”
- Dig deeper by asking, “What happens if this problem isn’t solved?” to highlight urgency.
4. “We Could Solve This Problem If ____”
Why it works: It forces customers to define the single biggest lever for success.
Ok, this technically isn’t a question but it IS the best open-ended discovery tactic you’ll ever find! Many discovery calls focus too much on how the salesperson’s solution can help, which can lead to a conversation that’s too focused on features instead of addressing the root problem.
Here you’re stepping back and asking your customer to consider the single biggest factor that would make the problem go away with no solution bias.
Their answer provides valuable insight into what they perceive as the biggest obstacle or opportunity—and it gives you a roadmap for aligning your solution accordingly. As a bonus, this strategy works so well because it’s simple and covers the three most important elements of a problem-centric discovery question:
- Focus: it drives right to the heart of the problem
- Alignment: if helps determine if you’re in a position to help them
- Novelty: it sounds different and is fun to answer!
How to use it effectively:
- If their answer aligns with your solution, reinforce the connection.
- If their answer doesn’t align with your solution, use follow-up questions to explore their reasoning. There may be a deeper issue at play that your offering can still help resolve.
5. “Does Your Team Actually Want to Solve This Problem?”
Why it works: It uncovers hidden resistance and internal politics.
Just because a problem exists doesn’t mean the organization is eager to fix it. For example, I recently spoke to a CRO who was looking for leadership training for his sales managers. “They’re an experienced bunch but they’re struggling with coaching and driving accountability within their teams”, he said. After diving deeper into the root cause of the problem and determining my curriculum could help I stepped back and said, “If you don’t mind me asking…do your sales managers want training? I ask because sometimes people who’ve been doing something the same way for a long time can be resistant to change. Do you think they’d be open to it?”
The reality is, to make any solution work, the people responsible for using it or putting it into action need to be bought in and aligned. And if internal resistance, competing priorities, or fear of change are poised to delay or kill your deal or cannibalize the success of your project, it’s important to know that. This question helps uncover those hidden obstacles.
How to use it effectively:
- Explore the risks by asking: “Who might resist this change, and why?”
- Help them strategize ways to gain buy-in from hesitant stakeholders.
- If you feel your line of questioning might be seen as sensitive or contentious, you can use my “Simple Reasoning Phrase” tactic to help your customer feel comfortable opening up.
The Bottom Line
Great sales discovery isn’t about checking boxes—it’s about sparking high-value conversations. The best questions aren’t the ones that get fast answers; they’re the ones that make customers stop, think, and share insights they wouldn’t have volunteered otherwise.
So the next time you’re in a discovery call, swap out the typical “What are you looking for?” with one of these more thought-provoking questions. You’ll get better answers, uncover deeper insights, and ultimately close more deals.
