The Power of Asking "What Is a Challenge You Are Facing?"

In a typical enterprise sales call, prospects are often braced for a barrage of product features and slides. But picture a different approach: the sales engineer begins the conversation not by pitching, but by asking, “What is a challenge you are facing right now?” This deceptively simple question can transform a sales interaction. It signals a shift from a product-centric monologue to a customer-centric dialogue. In an age where B2B buyers are inundated with promotional emails and cookie-cutter demos, such a consultative opening stands out. Research shows that using a consultative, needs-focused approach is the most effective way to engage today’s buyers. By asking about the prospect’s challenges, sales engineers immediately put the focus where it belongs – on the customer’s problems and goals – setting the stage for a deeper connection.

Customer-Centric Selling

Modern B2B buyers expect salespeople to act as strategic advisors who understand their business, not just as product pushers. This shift is driven by a simple reality: no problem means no sale. In other words, customers only buy solutions to problems that they perceive as important. If a seller does not uncover a real challenge the customer is facing, there is little reason for that customer to change the status quo.

Embracing this truth, consultative selling focuses on uncovering and addressing the buyer’s needs through dialogue. In practice, that means asking open-ended questions, listening actively, and tailoring your approach to each customer’s unique situation. The question “What is a challenge you are facing?” exemplifies this approach by immediately inviting the buyer to share their needs and pain points. It transforms the sales engineer from a product lecturer into a problem-solver and advisor.

Neil Rackham’s seminal research on high-performing salespeople (which gave rise to the SPIN Selling methodology) found that top sellers differentiate themselves by the questions they ask. Rackham observed that “top performing sales people ask far fewer situational questions, and far more effective problem and implication questions, than their lower-performing peers.” In essence, average sellers might pepper a prospect with factual queries (e.g. “How many users do you have?”) or jump straight into a pitch, whereas the best sellers zero in on the prospect’s pains: “What’s not working with your current process?” or “What challenges are preventing you from hitting your goals?” By doing so, they uncover the “problem behind the problem” and can add value by addressing it. This approach aligns with Rackham’s finding that successful salespeople don’t merely communicate the value of their solution – they help the customer discover the value by first uncovering an important problem to solve.

Why Asking About Challenges Is So Effective

1. It Puts the Customer (and Their Story) First. The act of asking a prospect about their challenges immediately signals that this conversation is going to be about them, not about your product. That’s a powerful differentiator. Many buyers have been conditioned to expect a sales pitch – so when a sales engineer starts by inquiring sincerely about the buyer’s problems, it’s disarming (in a good way). By inviting them to talk about those pain points, you demonstrate empathy and build trust. Psychological research shows that people feel more bonded and satisfied in conversations where they get to talk about themselves and their concerns – it activates the same reward centers in the brain as food or money.

Importantly, this question is open-ended, inviting a narrative rather than a one-word answer. It cues the customer to reflect and then tell the story of their problem. That story is gold for a sales engineer. Within it lie the clues to how you can help – the pain points, the implications of not fixing them, and the outcomes the customer cares about.

2. It Uncovers Pain Points and Urgency. From a consultative sales engineering perspective, your ultimate goal is to identify a problem you can solve that delivers value to the customer. Asking about the prospect’s challenges is the quickest path to finding that problem. It prompts the prospect to lay their cards on the table: maybe they’re struggling to reduce cloud costs, or their marketing team is frustrated by how long analytics reports take, or they’re losing deals due to an inefficient CRM workflow. Whatever the issue, once it’s voiced, you as the sales engineer can zero in on it.

Getting on the same page about the customer’s challenge is more than a pleasantry – it’s directly linked to closing the deal. Conversely, if the seller misunderstands or glosses over the real problem, the chance of winning plummets (“misdiagnosis can kill deals,” as the report says). The question “What’s a challenge you’re facing?” is the first step toward problem alignment. It invites the buyer to articulate the problem in their own words, and it ensures that you start addressing the issues they care about, not what you assume.

3. It Builds Trust and Signals a Partnership Mindset. Trust is the currency of complex B2B sales. A prospect who feels heard and understood is far more likely to view you as a partner rather than just another vendor. The simple act of asking about their challenges – and truly listening to the answer – builds credibility. It shows humility (you’re not assuming you know their problem) and genuine curiosity. Sales psychology experts often cite the “law of reciprocity” in conversation: if you show interest in someone else’s issues, they are more likely to trust and open up to you. There’s also the factor of emotional relief – many decision-makers feel pressure and even isolation in dealing with their company’s problems. When a sales engineer creates a safe space for them to discuss a pain point, it can be cathartic. It positions the sales engineer as an ally who is there to help solve that problem together.

4. It Differentiates You in a Competitive Market. In competitive SaaS markets, products can start to sound similar. Features and pricing may not provide much uniqueness. The sales experience itself becomes a differentiator. When a prospect has conversations with multiple vendors, the one who truly listens and grasps their problem will stand out. Anecdotally, buyers often recall sales meetings where the rep talked at them for an hour – and not fondly. Contrast that with a meeting where the sales engineer spent the time asking smart questions about the buyer’s needs and then mapping the demo to exactly what the buyer requested. Which vendor leaves a better impression? The latter not only uncovers the challenge but can then vividly demonstrate a solution to that challenge. By starting with “What challenge are you facing?”, you set up a tailored value demonstration that your competitors might miss. You effectively allow the customer to “write the script” for what they want to see from you. The best demos are 100% about solving the customer’s problem, and 0% about flexing every feature. You won’t know which 10% of features matter to this customer unless you first find out what their challenges and goals are.

5. It Sets Up a Tailored, Impactful Demo or Solution Discussion. For sales engineers in the SaaS world, the demo or technical discussion is often where deals are won or lost. Asking about challenges at the start of a call ensures that when you do show your product, you’re focusing on the most relevant parts of it. You can connect the dots explicitly: “Earlier you mentioned that onboarding new users is a major challenge. Let me show you how our solution addresses that…” Instead of a generic walkthrough, the prospect feels like, “Wow, this demo was made for me.” This relevance can dramatically increase engagement.

Q: What if the prospect exposes a challenge we can’t solve?

This worry can make some salespeople avoid asking in-depth questions. There’s fear that the prospect might reveal a big issue that your product doesn’t address – and now you’ve opened a can of worms. However, this scenario is actually beneficial in the long run. If the prospect’s main challenge is truly outside your solution’s scope, it’s better to know that early. You can then either (a) qualify out of a losing deal tactfully, or (b) set realistic expectations and focus on the parts you can help with. Honesty is key here. For example, if a prospect says their biggest challenge is something your platform doesn’t handle, you might respond, “I appreciate you sharing that. Based on that, I want to be upfront: our solution isn’t designed to [solve that particular problem] as deeply as some others. We typically address [related problem]. If that primary challenge is your main focus, I can recommend [resource or even a competitor]. If it’s one of a few priorities and you’re also looking at [problem your product solves], I’d be happy to show you how we could help on that front.” This kind of transparency builds enormous trust. In some cases, the prospect might reveal additional challenges you can solve once they see you’re not just going to force-fit your product. And if not, you likely saved both parties a lot of time.

Q: What if the prospect is caught off guard or uncomfortable with such a direct question?

First, establish a bit of context and rapport before diving into the big question. Avoid a robotic “checklist” type of discovery that feels like an interrogation. Sending an agenda before the call can also prepare the prospect and make them more comfortable.

Second, adjust the phrasing or approach if needed. Some experts suggest that asking a completely open question like “What challenges are you facing?” can sometimes be too broad, leading the prospect to either ramble without focus or clam up because they’re unsure how to answer. One mitigation strategy is the “multiple-choice question” or what some call the “menu of pain.” Instead of an essay question, you give the prospect a few common challenges to choose from. For example, “From talking to other CISOs, we often hear three big cybersecurity challenges lately: A, B, and C. I’m curious, which of those is most relevant to you – or is there another challenge that tops your list?” This approach makes it easier for the prospect to answer

Third, if a prospect truly seems uncomfortable or unsure (maybe they respond with, “Uh, I’m not sure, I just wanted to see a demo”), you can pivot gracefully. One tactic is to share a quick anecdote: “Sure, we can absolutely go through a demo. Just to ensure it’s relevant, let me share what we did with another client. They were struggling with X, and we helped reduce that problem. Do you experience anything similar, or is there a different area you’re looking to improve?” Storytelling can prime them to open up.

Q: Could this question lead to long, unfocused tangents?

A valid concern is that a broad question might open floodgates – the prospect might start venting about everything that’s wrong at their company. In a limited time call, how do you manage that? Indeed, some sales trainers caution reps to maintain control of the conversation; they fear that asking “What’s your biggest challenge?” could result in a 15- minute monologue by the prospect that doesn’t actually lead toward a sale. However, rather than avoiding the question, the skill is in artfully guiding the conversation. It’s a great problem to have too much information from the prospect versus too little! If a prospect is passionately describing their challenges, practice active listening techniques: take notes, interject with “uh-huh”, “I see”, and summarize occasionally: “So if I understand, the two big issues are A and B, and A is causing you XYZ pain, right?” This not only confirms your understanding but can gently steer them. If they go off-topic, you can acknowledge what they said and pivot: “It sounds like there’s a lot going on. To make sure we address what matters most, can I ask – of those issues, which one is having the biggest impact on your team right now?” Or even with some humor: “If we tried to fix everything all at once we’d need a magic wand. If we had to pick one or two major challenges to tackle this quarter, which would those be?” By refocusing on prioritization, you keep the discussion productive.

Q: Some buyers just want to see the product – won’t they get impatient with questions?

Occasionally, you encounter a prospect who is very solution-driven. They might respond to discovery questions with curt answers or say something like, “I know our problems, I just want to see what your tool can do.” This can happen especially with technical buyers or if they’ve already done a lot of research. In such cases, you adapt rather than force the issue. You might say, “Absolutely – I can dive into a demo. To make it most relevant, I’ll tailor it on the fly as we go. Feel free to interrupt me with questions. And as we go through, I may ask a couple of small questions just to ensure I’m addressing what you care about.” Then, as you demo, you can still ask mini- questions: “Is this part relevant to you?” or “How do you handle this currently?” The prospect may gradually open up once they see the product context. The lesson is: be flexible. If the direct question up front isn’t landing due to the prospect’s style, you can weave the discovery into the demo rather than abandon it entirely.

It’s worth noting that many times when a prospect resists discovery questions, it’s because they’ve had bad experiences with superficial sales reps in the past. They might think “Ugh, here comes the checklist of 20 questions that wastes my time.” To overcome that, differentiate your approach. Make it a conversation, not an interview. And if you sense tension, address it transparently: “I know your time is valuable. The reason I’m asking these questions is so I don’t waste time showing you things you don’t need. Once I understand your challenges a bit, I can zero in on exactly what will help. But if you’d prefer, I can give a brief overview first and then we can circle back to what matters most to you – just let me know what you’d find most useful.” This kind of customer-centric flexibility often disarms their impatience. You’re saying “I’m here to be helpful on your terms.” Sometimes they’ll then say, “No it’s fine, go ahead with your questions.” And sometimes they’ll take you up on the offer and say “Okay, show me a little first.” Either way, you’re demonstrating respect and adaptability, which again builds trust.

Q: Could revealing challenges make the prospect feel vulnerable or defensive?

In some contexts, a buyer might fear that admitting a big challenge is like showing weakness – perhaps they worry a salesperson will exploit it or judge them. This is where creating a safe, consultative atmosphere is crucial. Reinforce that you ask everyone these kinds of questions and that it’s normal. You might share a quick anecdote: “One of our customers initially told us their challenge was X, and honestly, a lot of companies struggle with that. There’s no judgment on our end – the more we understand, the better we can help or determine if we’re not the right fit.” This assures them that you see this as a partnership, not a gotcha game. Also, how you react when they share a challenge sets the tone. If they say, “Our challenge is we have no formal process; it’s a mess,” respond in a supportive way: “Thank you for sharing that. You’re definitely not alone – I see that often, and it’s great that you’re looking to address it.” Validate their openness and never make them feel foolish for having that issue. If they sense empathy rather than judgment, they’ll continue to confide in you.

Finally, consider cultural factors. In some cultures or environments, talking openly about problems isn’t the norm until a relationship is established. If you’re on a first call with a very large enterprise or an international client, for example, you might modulate how you ask. Maybe start with more factual or goal- oriented questions (e.g. “What are your objectives for this year in XYZ area?”) before “What challenges are you facing?”. Essentially, earn the right to ask deeper questions by demonstrating respect and maybe sharing some value first (like an insight or two). This mirrors the finding from social science that opening with slightly less intrusive questions and building up yields better rapport

Actionable Tips

For sales engineers (or any consultative seller) looking to leverage this powerful question, here are some practical tips and best practices to make the most of it:

• Do Your Homework First: Before any discovery call or demo, research the prospect’s company and role. Look for clues about what challenges they might be facing.
• Set the Agenda and Expectations: At the start of the meeting (or ideally in an email beforehand), let the prospect know that you’re going to ask about their challenges and goals.
• Lead with Empathy and Curiosity: When asking “What challenges are you facing?” or any variant, keep your tone warm and genuinely curious. This isn’t an interview or interrogation; it’s a conversation.
• Probe for Depth and Clarity: The initial challenge question opens the door. Once the prospect walks through it, follow up with additional questions to really understand the problem. These probing questions should be used tactfully – don’t machine-gun them one after another. Weave them in naturally as the prospect speaks:
  • “How long has that been a challenge?”
  • “What have you tried so far to address it?”
  • “Who on your team is most affected by this challenge?”
  • “If you could solve this, what would it mean for the business (or for you)?”
  • “Why now? What happens if this challenge isn’t solved soon?”
• Connect Challenges to Solutions (Tailor Your Demo/Presentation): As you gather challenges, start mapping in your mind (or notes) which aspects of your solution address them. When it’s time to show your product or explain your offering, explicitly link back to what the prospect said. Use their language where possible.
• Use Stories and Examples: When appropriate, share short case studies or anecdotes during the conversation that relate to the challenge.
• e Honest and Set Boundaries: If during the discovery it comes out that some challenges are outside your scope, be honest (as discussed in counterarguments). It’s perfectly fine to say, “We might not solve that piece directly, but we do solve this other part of the problem.”
• Practice Active Note-Taking and Documentation: During the call, jot down exact phrases the prospect uses when describing challenges (if you’re not already recording/transcribing with permission). Those notes are gold for later steps.
• Educate and Reframe if Needed: Sometimes, a prospect’s perceived challenge might not be the real root problem. Through skillful questioning, you might discover the issue is different than they initially thought.
• Close the Loop in Follow-Ups: Every touchpoint after the call should reinforce that you remember and care about their challenges. In your thank-you email, recap their challenges and how you’ll address them.

Using the "What Is a Challenge You Are Facing?" question is not a one-time tactic; it’s part of a broader mindset of customer-centricity. Even after a sale, a great sales engineer will continue asking the customer about challenges during implementation, quarterly business reviews, etc. This positions you for upsells or renewals because you’re continuously aligning with the customer’s evolving needs. In a SaaS context, where customer success is crucial, sales engineers often remain involved as technical advisors. Carry that consultative approach forward – ask about new challenges that have arisen and help solve them (whether through new features, additional training, or even recommending other tools). This will strengthen your relationship and make you a true trusted advisor in the long run, not just through the initial sale.