11 Discovery Questions to Ask Prospects to Help You Build a Deal-Winning Demo Environment

Selling is an art and science that can deliver transformative results for any organization. And the sales discovery phase is the most important stage of the sales process.

It’s when you build your awareness of client needs, understand their motivations, determine product fit, and uncover the obstacles for your deal. In essence, discovery calls set the stage for the entire sales process and significantly influence outcomes.

While most sales reps understand the importance of discovery calls, many still make a mess of them. 

Data suggests that roughly 40% of sales representatives say they make calls without sufficient information. As a result, the on-phone, and in-demo experience disappoints most prospects and clients.

So, where do things go wrong? 

First, it’s vital to understand that it’s not about pressuring prospects to buy when you schedule a discovery call. Instead, it should be about helping them realize the value they can get from your offering.

You can only achieve this by understanding their needs, desires, and pain points. To accomplish this, you’ll need to ask the right questions during the sales discovery process. 

Read on to learn some questions you can ask to make discovery calls more engaging and effective. 

1. What Should I Know About Your Company?

Discovery calls are not scheduled out of the blue. By the time it happens, there’s at least been an inquiry or proposal of how you can work together.

So, you must do due diligence and research the prospect to know a bit about them during the call. This demonstrates that you’re going the extra mile to meet their needs.

However, don’t assume that you know their brand well. Once you share what you’ve gathered about the company, ask the prospect to tell you a bit about their company.

Doing so allows them to introduce themselves on their terms and may reveal something you do not know.

This also allows you to begin to craft your demo environment. Hearing about the overall focus of companies, recent leadership changes, new goals, and more can help you figure out what problems you need your software demo to solve.

2. What’s Your Role and How’s the Day-to-Day Like?

Discovery calls significantly influence the outcome of the sales process. As such, you may be rearing to get into the nitty-gritty and close the deal.

However, if you get to the serious bits too fast, you may put off the client. Use the first few minutes to ease any pressure and get to know the person on the other end.

Ask them to tell you a little about their role and what it involves. This question may seem meaningless, but it allows you to build a connection. Don’t assume the same title you’ve seen 100x has the same responsibilities at each company. In our experience, similar titles vary greatly company-to-company.

Figuring out your prospect’s day-to-day activities also allows you to craft the perfect demo environment. Focusing on the tasks that take up the most time, for example, can help you focus on value propositions like giving them time back in their day. 

You should also focus on any dual roles. If your prospect spends a lot of time, or energy on problems you can help them solve, but they do so with other members of their team, try to get them to join the conversation as well.

3. What are Your Goals (Operational, financial, customer-related)?

At some point, you may need to sell your product directly. One of the most compelling cases you make is showing how it can help prospects achieve their goals.

You can get ahead of this situation by asking about their goals early on. Then, depending on your product’s value, you can focus your question on financial, operational, or goals related to employees and customers.

Furthermore, make the question time-bound. The timeframe should depend on how long it takes to set up your tool.

For instance, if your solution takes three months to implement, ask about their goals six months later. 

4. Which Challenges are you trying to Address?

By design, your solution helps clients solve particular challenges. And as you deal with more clients, it becomes clearer which problems they hope you can help them solve.

While these problems may cut across most of your clients, don’t make assumptions about the challenges prospects face. 

Allow them to bring up whichever challenges they’re facing. This will help determine the best way to package your offering. It will also help determine the best way to structure your demo environment. Showing how your product can directly address the customers pain points.

Knowing the problems a client is facing is great, but it’s not enough to help you solve them. You need to understand the root of the problem to present a viable lasting solution. 

So, make a follow-up question about the source of the problem.

5. Do You Have Problems With (Something related to the product)?

Once you’ve covered the general aspect of the prospect’s company and challenge, delve into more specific questions. 

The goal of this question is to get them to explore a challenge that you can solve. If they answer yes, let them explain the scope of the problem. Then, later on, when you showcase how your solution can solve that challenge, they’ll quickly embrace it. 

6. Can I Ask You a Difficult Question?

Offending clients is always counterintuitive, making them defensive and predisposed to reject any proposal you make. 

But this does not mean you always err on the side of caution. At times, to get the conversation to the next level, you need to stimulate critical thought by asking hard questions.

While asking the hard questions is essential, don’t go into them directly. Instead, begin by preparing the client psychologically for what’s to come and, at the same time, disarm them.

The easiest way of achieving this is by asking them for permission to ask difficult questions. Doing so takes the sting out of such questions. As such, the client will not feel offended or attacked. And they’ll try to answer the question to their level best.

As they do this:

  • They get a deeper understanding of the issue
  • You’ll identify areas to structure your pitch around

7. Where Is this on Your List of Priorities Today?

During the discovery call or demo presentation, it’s easy for both parties to get carried away by excitement. On your part, the idea of landing a new client is always welcome. Likewise, for your clients, the thought of finally finding a solution to a key pain point is cause for celebration.

However, even if everything seems aligned, the deal can fall through. This happens because it’s not a top priority for the client, or you don’t have a defined timeline. 

You can avoid such scenarios by asking this question. It allows the client to determine how much they want to implement it and how soon. In turn, you’ll know how much you can commit to the deal.

8. Can You Tell Me More About That?

You’re finally making progress, and the client seems to be buying into the idea. So, you want to use the momentum to get through the other questions. 

While it’s a great strategy, it should never come at the expense of clarity. Never proceed to the next question if there’s something you don’t understand fully. 

Telling a client that you don’t understand what they’re talking about will make you look incompetent. So instead, tell them you’re interested in that subject and ask them to tell you more about it.

9. If I Propose a Solution, What Would We Need to Do to Make It Happen?

Different factors affect how corporations adopt new solutions. These range from size, management style, urgency, etc. With some, you can begin implementing immediately after your interactive demo. On the other hand, there may still be a few more hoops to jump with some companies.

Therefore, even before going into depth about your solution, it’s essential to know the process that will follow. 

Key information you can get from this question include:

  • How many other people need to sign off on the project
  • How long it can take to get approval

10. What Other Possible Solutions Do You Have?

Suppose you’re on the other side of the call. Would you have only one option when looking for a solution that addresses critical challenges? 

Probably not. So, don’t assume the deal is done even if things are going well. 

Try and get a scope of what you’re up against by asking directly. Knowing your competition gives you a competitive advantage as you’ll see what you need to do to beat them.

11. Who Else Will Be Involved in Choosing a Vendor?

In most cases, the person you’re talking to is your point man in the company. However, it does not mean that they’re a decision-maker. And if they are, it’s likely they’re not the only ones.

This question will help you determine their influence on the process and final decision.

When dealing with an enterprise client, ask if they have written criteria for choosing vendors. If they do, accessing it will make it easier to check all their boxes.

Take Things to the Next Level with a Personalized Demo Environment

After incorporating these questions in your discovery calls, you’ll realize an increase in clients progressing to the next stage. Now that you’re closer to closing the deal, it’s time to take things to the next level. When they come in to see how your solution can work for them, ensure that you have a demo environment built for them. When you are ready to build hyper-personalized, live demo environments inside your software platform, we’re here to help!


Brian Cody

VP of Sales Engineering, Clari

Michael Stanczak

VP of Enterprise Sales, illumin

Ryan Splain

Principal Demo Solutions Engineer, Salesloft