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8 min read

Embracing Demo Discovery “On-The-Fly”

Embracing Demo Discovery “On-The-Fly”

Discovery “On-The-Fly” is when, for a variety of reasons, you have to run discovery in the same meeting as a demo. In this article, you’ll learn how to drive an effective meeting that includes both demo and discovery.

Demo Discovery

Let me start this article with clarity. We view Demo Discovery as the process in which you get as much information out of the people you’re going to demo to as possible. Simply put, the results of successful discovery produce your team’s path to winning the technical sale. This way, you can make the demo as focused, meaningful, and motivating as possible. The term “discovery” comes from the legal world regarding evidence discovery, and it’s the same concept. You’re trying to figure out how to build your case to win the technical sale through your demo. Ideally, discovery is performed ahead of the demo with every stakeholder involved in the decision.  

To illustrate the importance and subtlety of the discovery process, imagine being commissioned as a painter, and the client says, “My family loves the sky over New Zealand. Can we commission you to paint a watercolor of the New Zealand sky?” Hey, you’re a professional painter, of course, you can paint a picture of the New Zealand sky! The problem is you’re not in New Zealand, you’ve never been to New Zealand, and you need clarity on the family’s vision of what the New Zealand sky looks like to them. The easy thing to do is have them send you a picture of what they want but, they prefer that you paint from their descriptions. So, you ask, “When you look at the sky over New Zealand, what colors do you see?” to which she responds, “I see blue with white Nimbus clouds;” ask the family that same question and you get four different answers. You may ask additional questions about the time of day for the painting, the season for the setting, are their mountains in view of the sky, etc. When you finally finish your interviews, you agree on what the painting should look like and paint them a family heirloom.

Now imagine instead of painting the New Zealand sky, you’re building a demo. When you started with the company, how you demonstrated certain functionality was probably narrow, maybe even scripted, as if you’re painting from a photograph. You learned to make adjustments to your demo as you discovered the subtleties of the needs of individual prospects and stakeholders. The only way you knew to adjust was by asking Discovery questions ahead of the demo. 

Today’s Reality: More Demos, Less Time

Let’s back up to a pre-2020, in-person demo for a moment and discuss how PreSales professionals gained a perspective on stakeholder priorities. You weren’t following your sales methodology and sales process if you found yourself performing a significant amount of Discovery during the demo. The sales process was all about informed control of the prospect.  

Unfortunately, today’s B2B buying groups struggle to follow a buying process loosely, not a sales process. I say “loosely” because our global clients tell us that stakeholders regularly participate in demos with a seemingly endless list of undocumented requirements. A proper buying process should surface and document requirements so their vendor evaluations are consistent and complete.  

Additionally, there can be many occasions where one of your sales professionals initiated the opportunity, and your only true competitor is “status quo.” This situation is common with existing clients where a client success or account executive is trying to convince the client to replace an existing process or piece of technology with yours. The stakeholders are hastily assembled for a demo, and the stakeholders begin firing random requirements at the demonstrator. 


The other problem with attempting to perform traditional Discovery on today’s buying groups is discovery fatigue. Throughout the stakeholders’ careers, they have endured long, tiring, feature-dump demos and presentations. Your upcoming demo isn’t the first time these stakeholders have sought a technology solution, product, or service similar to yours. Let’s say you’re a software firm trying to sell your “spend management” solution to a large public corporation. Over the past ten years, their team has implemented a variety of accounts payable and spend management solutions. The prospect just hired their third CFO in that same time period. The new CFO wants the team to evaluate what she used at her last organization.  

The stakeholders are fatigued by another set of software companies, who again ask the same (or similar) discovery questions. They don’t want to set time aside to answer a bunch of questions. The stakeholders are thinking, “Not again! These people should know our business, and we sent them everything they need to know, so why do they need to talk to us?” Additionally, they’ve experienced poor demonstrators that consumed their time with discovery questions but never used what they learned during the demo. Talk about frustrating!  

Consequently, it becomes difficult to secure time with stakeholders because they don’t want to go through this anymore. They don’t want to spend the time, even though it could be of value to the process. Instead, they tell the stakeholder that’s leading the selection (often called the sponsor), “You talk to them on our behalf.” In the end, you only conduct Discovery with the sponsor. 

There is a considerable risk in this; it’s a matter of whether the information the sponsor is giving you is accurate and comprehensive or if they’ve filled in the information gaps themselves. The sponsor has one role in the company and, therefore, one perspective. That means he might not be able to understand what the others—the staff members or upper management—need from your demo. You end up with incomplete, or even inaccurate, information.  


“It’s not necessarily that the information is unknown, but rather underknown.”

When Chad Wilson, our Vice President of Operations, made that statement in a senior management meeting, I was struck by his clairvoyance. He reflected how our global facilitation team had heard about a significant shift in client access to interpersonal Discovery. Upon further investigation, we learned through client conversations that prospect sponsors were rarely allowing sales engagement teams broad access to stakeholders. Instead, sponsors were funneling discovery meetings to them and speaking on behalf of all stakeholders. Consider these two data points from our research: 

We asked research participants to complete the following sentence:  

Compared to four years ago, my opportunity to perform pre-demo Discovery is

From the data above, you would be right to conclude that discovery opportunities are about the same as they were four years ago. Discovery is still happening, but as we learned in follow-up interviews, with fewer stakeholders and using different methods than person-to-person interviews. The problem is exacerbated by the fact that organizations like CEB/Gartner report an ever-increasing number of stakeholders in every B2B decision. Making matters worse, sales engagement teams report a 48 percent decrease in the amount of time they’re given to prepare for an effective service presentation. These facts lead to underknown information from Discovery when engaging in a critical client engagement like a finals demo. 

Presenters tend to fill in the gaps caused by the limited Discovery of the underknown with what they know from their experience working with other customers. Presenters often plan for a demo with dangerous assumptions, and they are invariably going to have issues. 


Transparently, no formula for human interactions is ever perfect—but this one is damn good! It involves active listening skills on the part of the sales engagement team member, and that’s always a good thing! It demonstrates empathy and interest in helping the individual contributors move from their current situation to their desired position. It helps managers think about the impact of their team members moving from current to desired. It uncovers scenarios to create the context for important demo tell-show-tell topics. It seeks metrics that help build the case for the value that executives need for justifying your products, services, or solutions.  

Let’s say a group of stakeholders has invited you and your team to schedule a virtual demo to address a list of eight items of interest. During the demo, you’re discussing item number four on their list, and there are six ways your solution can address the needs of that item. Do you demo all six ways? Or do you try to find out which two methods will be the most relevant and let those be the two explored in the demo?  

We recommend you promptly demo the two ways that make the application look simple and easy to implement. Simplifying this topic also gives you more time to present the other solutions, making your entire solution look less complicated. To accomplish this simplification, you need to understand and build context around item four by asking them a few questions. In other words, you need to be agile about how you do that.  

When you get to item number four, ask a leading open-ended question about the topic. Compare these two questions about forecasting inventory for a wholesaler: 

  1.  “Tell me what forecasting methods you prefer.” (Open-ended)
  2. It has been our experience that organizations like yours, prefer simple averaging for many products, but exponential smoothing for select, higher volatility products. What is your opinion on this?” (Leading open-ended)  


“Be as open-ended as possible.” Many of us have been trained to use the approach of question one. However, stakeholders want to know that you have an opinion and position, and part of what they are buying is your expertise. Rich, leading, open-ended questions build trust by demonstrating your expertise. Many people will judge you and your professionalism by how you ask questions, not by how you demo. 

Additionally, in the past, you had time to build a relationship with stakeholders through interpersonal Discovery, which strengthens trust and comfort. The sponsor often limits your Discovery’s scope with today’s selections, leading to a lack of individual stakeholder relationship building. Pure open-ended questions place a stakeholder in an uncomfortable position. The stakeholders don’t know if they should open up and tell you everything they know—leaving themselves exposed to what they don’t know.  

In contrast, the expertise built into the leading open-ended question above creates credibility and trust. Stakeholders will appreciate the fact that you have an opinion and will answer your leading open-ended question thoughtfully. Your leading open-ended questions drive toward your service strengths, which, taken as a whole, is where your advantages lie. 

By the way, you should never spend the first thirty minutes of the demo asking leading open-ended questions about all eight of the items they want to be demonstrated. Instead, intersperse your Discovery on-the-fly questions throughout the event, then demo responsively to the information learned; that’s being agile.  

When you perform Discovery On-The-Fly (OTF) and responsively demo, you get on and firmer ground, which helps ensure your future questions are relevant. You keep the questions contained in the topic around what you are about to demo or present a solution against. You could probably expand your questioning and the conversation and go into various other topics, but if they’re not relevant to what you want to demo next, they’re not productive.  

The skill here is all about keeping your leading open-ended questions narrow and knowing when to stop the questioning and do the demo. We call this “narrowing.”  

Today’s stakeholders will get frustrated if you spend too much time asking broad, open-ended questions that lead to multiple topics in unrelated areas. And you will be frustrated since the value of your solution will be lost in a sea of possibilities—making your demo ineffective.  

You might be wondering, “How do I build a library of insightful leading open-ended questions?” The answer lies in your experience and expertise. You already know the problems your services solve, so draw on that for the front end of your leading open-ended questions.  

For example, suppose I presented a solution that conserves energy in a commercial building; in that case, a leading open-ended question could be created out of one of the many methods I offer that help accomplish that goal. For example, “Many of our clients have found that intelligent, interconnected, zone-based thermostats that detect if someone is in a room help save as much as eleven percent of the total energy consumption of the building. I’m curious, what are your current strategies in new construction for temperature control and energy conservation?” 

The “leading” portion of this question is a statement (not a question) derived from a key feature of the solution and turned into a key-value benefit of the results from this feature. The information was derived from a case study of an existing customer. The individual asking this leading open-ended question took that insight and placed it at the front end of their open-ended question. Doing so results in a confident, expertise-laden narrowing question that leaves room for the stakeholder to express their opinion and will help you build context for this portion of your demo or presentation. 

Once you’ve completed Discovery OTF on a topic, you have a decision to make. If you’re prepared, configured, and ready, you can choose to demo with the information you just learned responsively. Remember to use what you learned in the opening tell (context setting) of the demo topic. Next, only show what you need to address what you learned in your Discovery OTF. Finally, don’t forget to deliver the benefit of what you just demonstrated in the form of a closing tell. You’re now ready to move on to the next topic.  

The Bedrocks of Discovery 

As discussed earlier in the article, historically, demo discovery preceded the demo by days or even weeks. Discovery was often in-person interviews at the prospect’s location. Some might think that changed in 2020 when all Discovery went virtual. But, as described by the book “Rule of 24“, Discovery was becoming abbreviated and transitioning to virtual long before 2020. Today, a smaller and smaller percentage of demos are preceded by extensive discovery interviews. The current business climate dictates new rules and circumstances for Discovery. 

Broadly speaking, contemporary Discovery consists of eDiscovery, Pre-Demo Discovery interviews, and Discovery On-The-Fly during a demo. This author is not suggesting that Discovery OTF should replace eDiscovery or Interpersonal Discovery, and these styles of Discovery need to remain your bedrock for compelling demos. Sales professionals should never rely on a PreSales professional with outstanding Discovery OTF skills. It remains imperative that the sales engagement team drives prospects to interpersonal Discovery to ensure the most effective demo possible. However, the future success of your demos will be predicated on your ability to embrace Discovery OTF skills during a live demo. 

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