It’s often said that “the quality of the questions you ask will determine the quality of the conversation.” While this may sound cliché, it’s more true than you might realize, especially in complex enterprise sales—and in your demos.
As sales professionals, we’re often so eager to showcase our solutions that we forget that demos are about more than just showing off features. They’re about understanding the buyer’s needs, uncovering pain points, and forging a deeper connection.
Unfortunately, too many sales demos fall flat because we ask the wrong questions — ones that don’t spark insightful conversations or push the buyer to think critically about their challenges. Worse, some of these “bad” questions can make the buyer feel like you’re not really listening or understanding their needs. Or they provide you with false-positive feedback. This sounds positive, at first glance, because you have been asking a hypothetical question, that led to a hypothetical response.
So, how do we move from asking easy, ineffective questions to asking the ones that lead to deeper, more meaningful conversations? In this post, I’ll explain the difference between bad demo questions and better ones and why asking the right questions is crucial for closing deals faster, building trust, and becoming a true consultative partner.
The Problem with Bad Demo Questions
At the surface level, “bad” questions seem harmless. They’re often easy to ask and give you something to work with during the demo. However, these types of questions rarely lead to deeper insights or help you connect with your buyer on a meaningful level. Let’s look at a few examples of bad questions and why they’re ineffective.
1. “Does that make sense?”
This is one of the most common questions asked in a demo. It feels natural — a way to check if the buyer understands. But the problem is, it’s a yes/no question that doesn’t encourage deeper engagement. Even if the buyer doesn’t fully grasp what you’re saying, they’ll often just say “yes” because they don’t want to admit confusion. Instead, you need to ask open-ended questions that promote discussion and get the buyer to articulate what they’ve learned.
Better Alternative: “Is this what you had in mind?”
This question forces the buyer to reflect and provide feedback that’s more valuable. It gives you a sense of how well the solution fits with their current understanding, while also revealing any gaps in their knowledge and giving you insights into their thought process.
2. “Is this the kind of solution you were looking for?”
While this question may seem like a way to confirm interest, it’s too binary. A simple “yes” or “no” doesn’t provide any insight into the buyer’s true motivations, challenges, or buying criteria. Moreover, if the buyer says “yes,” it doesn’t necessarily mean they’re committed to your solution.
Better Alternative: “How are you currently doing this? How often?”
This question invites the buyer to open up about their current practices and the issue’s magnitude. You get a clearer picture of what they’re prioritizing, which helps you tailor your pitch to address those specific needs.
The Power of Open-Ended Questions
Open-ended questions are among the most effective types of questions in a demo. Open-ended questions are key to driving conversation, building rapport, and encouraging the buyer to reflect on their needs and goals. These questions can’t be answered with a simple “yes” or “no,” which is why they provide far more meaningful insights.
Let’s look at a few examples of open-ended questions that can transform your demo conversations:
1. “What’s the biggest challenge you’re facing right now in [area of interest]?”
This question helps you uncover the buyer’s pain points and gives you insight into where they need help. It’s not just about what they want; it’s about what they need, and that’s a crucial distinction when it comes to selling solutions.
2. “How does your current solution fall short of your expectations?”
This question encourages the buyer to reflect on their current frustrations, providing you with the opportunity to address why your solution is a better fit.
3. “How is this different from what you are doing today?”
This question allows the buyer to think about their pain points in a new way. And at the same time, it helps you understand their current processes and where your solution can deliver the most value.
4. “What else have you tried?”
Just because your customer has acknowledged a problem, it does not necessarily mean that they are looking to solve it. Oftentimes, the problem is latent and needs to be more painful to build a business case around it. Asking about their past actions to overcome the issue provides you with good intel whether you are dealing with a real problem, or just some “nice to have” that won’t qualify for a robust business case. If they have not tried anything in the past – you better look for another issue.
Moving Beyond Hypothetical Questions
Hypothetical questions are often tempting because they allow you to dream about potential outcomes or future scenarios. However, they can sometimes feel disconnected from the buyer’s real-world challenges. For instance, a question like, “If we could solve this problem for you, how would that impact your business?” is likely to get a noncommittal response because it’s asking the buyer to imagine an ideal world.
Instead, focus on situational and behavioral questions that dive into past experiences and current struggles. These types of questions are more grounded in reality and give you insights that are directly applicable to your solution.
Better Alternative to Hypotheticals: “Tell me about a time when you faced a similar challenge and how you handled it.”
This question forces the buyer to recall real situations, giving you a better understanding of how they approach challenges. You’ll also get a clearer picture of the existing gaps that your solution can address.
Rule of Thumb: Ask people about what they have done in the past, not what they think they’d to in the future!
Proactive Discovery: Asking the Right Questions Early and Often
Discovery shouldn’t stop after the initial call or meeting. While early discovery is crucial, it’s also essential to ask questions throughout the entire sales process. The best salespeople continue their discovery even during the demo or while negotiating the deal. This approach allows you to address objections in real time and adapt your pitch as new information arises.
In fact, proactive discovery isn’t just about asking questions — it’s about asking the right questions at the right time. For example, if you’re nearing the end of a demo, and you sense that the buyer is hesitant, asking a question like, “What’s holding you back from moving forward with this solution?” can surface concerns that you can address before they derail the deal.
Why Better Questions Matter
Bad demo questions don’t get to the heart of the buyer’s needs. Better questions, on the other hand, help you uncover deeper insights, address objections early, and present your solution in a way that truly resonates. By asking better questions, you can:
- Uncover Hidden Pain Points
The right questions will help you identify the challenges that your buyer may not even have articulated yet. These insights will allow you to position your solution as the right fit to solve their most pressing problems. - Build Trust
Buyers want to feel understood. Asking insightful, open-ended questions shows that you care about their needs and that you’re not just there to push a product. This builds rapport and positions you as a consultative partner, not just a salesperson. - Create Opportunities for Objection Handling
When you ask the right questions, you invite your buyer to share concerns, whether they’re about pricing, implementation, or fit. The sooner you know about these objections, the sooner you can address them and keep the sales process moving forward. - Differentiate Your Solution
The more you know about the buyer’s needs and challenges, the better you can differentiate your solution. The better your understanding of their unique situation, the more tailored and relevant your demonstration will be.
Closing Thoughts
The questions you ask during a demo are far more than just conversation starters — they’re your key to uncovering the true needs of your buyer, building trust, and positioning your solution effectively. By replacing surface-level, yes/no questions with thoughtful, open-ended ones, you’ll create deeper, more meaningful conversations that move the sales process forward.
So, what’s next? It’s time to start asking better questions. When you embrace the power of discovery and begin asking questions that dig beneath the surface, you’ll not only have more productive demos, but you’ll also build stronger relationships and close more deals.
And remember, discovery is an ongoing process. Don’t just ask the right questions once — ask them throughout the entire sales cycle. This will help you stay ahead of objections, uncover new opportunities, and position yourself as a trusted partner.
If you’re looking for more practical tips on how to improve your demo questions, feel free to download my cheat sheet with 54 meaningful demo questions for the most common demo scenarios:
