Discovery on the Fly? Some Plane Thinking


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[A slightly edited excerpt from the new book Doing Discovery]

“On the fly” is generally defined as doing something rapidly, without preparation, and on the spur of the moment. Most software organizations would refine this to combining a demo with discovery – a “disco-demo” – often characterized by alternating between showing capabilities and exploring the prospect’s level of interest.

The temptation can be strong to try Discovery on the Fly, particularly when the prospect initiates an inbound lead by clicking the “Book a Demo” button. After all, they want to see a demo, right? We’ll just ask them a few questions along the way…

Losing Airspeed…

Sadly, these questions are often less about actual discovery and more focused on what the prospect is seeing in the demo, such as, “What do you think of this feature?” or “Can you visualize your team using this?” By definition, when you are showing your software in a demo, most of your questions – and your prospect’s questions – will be centered on the software. After all, humans are visual creatures and we tend to react to what we are seeing.

That’s one of the major challenges – and risks – of attempting Discovery on the Fly. There is an extremely strong tendency for vendors to focus on the capabilities of their software, largely ignoring the many (many!) other discovery topics. Accordingly, it often takes the form of a standard “intro” demo, with a few questions mixed in along the way.

So why is this problematic? Let’s start with an analogy…

Visualize a photo of a 1930’s airplane flying at 10,000 feet (3048 meters), with the pilot trying both to fly the plane and troubleshoot a balky engine. It is pretty difficult for that pilot to look anywhere but at the plane’s instruments and certainly not a time to enjoy the view (which is truly terrific, but the pilot can’t spare time to take it in).

But wait, there’s more! There are two other planes headed right for the pilot’s plane, but the pilot doesn’t see them coming… And there is also a bank of very dark and dangerous storm clouds dead ahead. But again, the pilot is fully occupied by keeping the wings level and trying different fuel/air mixture combinations, switching tanks, checking the electrical system…

That’s one of the biggest challenges with Discovery on the Fly: you are fixed on the immediate problem and ignore everything else. You focus on your software’s features and are likely to ignore other discovery topics and opportunities.

Flying on Instruments

Let’s say our pilot has fixed the problem with the engine and all appears well again. The plane enters a bank of clouds and visibility drops to zero, forcing the pilot fly completely on instruments with no input from outside.

This is perhaps a more accurate analogy for doing Discovery on the Fly, because all that can be examined is within the airplane itself. There is no exploration of the territory the plane is flying over; no ability to determine forest from desert or even land from sea.

Is there a city nearby? Can’t tell. Countryside and farms? Don’t know. Mountains ahead? Unknown. All the pilot can see is the mist of the clouds surrounding the plane.

In doing Discovery on the Fly, this is similar to focusing solely on the software being presented. And while there are no limitations to asking other discovery questions that go beyond the screens being viewed, most presales and salespeople act as if they are on instruments, focusing only on the software.

They miss the opportunity to explore pain more deeply, uncover Related Pains, investigate Impact, examine Value, Demographics, Environment, Culture and other important elements of discovery. Like our pilot, they have their heads in the clouds – or more accurately, their software.

A loss of visibility is only one risk, however…

Stalling Out – “Buying It Back”

Attempting Discovery on the Fly often causes the negative result known as “Buying It Back”. In a traditional demo – and, in principle, any demo done without prior discovery – each capability you show will fall into one of the following categories:

  • Must have;
  • Nice to have;
  • Neutral;
  • Don’t need it;
  • Really don’t need it.

The “must have” and “nice to have” capabilities are all great and should become the Specific Capabilities desired by the prospect. But what about “neutral”, “don’t need it”, and “really don’t need it”? Each time the prospect sees one of these in your demo they think, “Well, I don’t need that – and I certainly don’t want to pay for it.”

And since they have just seen these superfluous capabilities demonstrated, they know that they will be paying for these features as part of the license fee. One or two small capabilities isn’t much of a concern, but when their perception grows to where there are several or many features that they won’t use – especially capabilities that are positioned during the demo by the vendor as major or high-value – then prospects get concerned.

They wonder, “Why should I have to pay for all of these if I’m not going to use them?” And when it is time to negotiate the price, your prospect says, “You know, you showed us a lot of capabilities that we’ll never use – so you need to reduce your price accordingly. We don’t expect to pay for things we won’t use.”

Counterintuitively, most vendors believe that, “The more capabilities; the more value…” This has been part of the reason vendors try to pack as many features and functions into demos as possible. They believe that by showing more and more, the perceived value of their software should similarly increase.

But prospects only want to pay for the capabilities they expect to use. This is one of the biggest risks of doing Discovery on the Fly: Buying It Back.

The tendency of vendors to fall into this self-made trap is huge and happens far too frequently, particularly when trying to do Discovery on the Fly. The temptation to dive further into your software is extremely high when it is already launched and on the screen!

Leveling Off

There are two solutions to avoiding Buying It Back:

1. Introduce your capabilities in the form of a question before showing them.

If the prospect responds positively, then you can say, “Well, we have that capability – would you like to see it?” On the other hand, if your prospect’s response is, “No, we don’t really want that….” or “We can’t see situations where that would be valuable,” then you simply move on and don’t show that capability.

Note that if the negative response happens too frequently, you are still at risk of Buying It Back, since your prospect will begin to assume that all of these capabilities will be in the product they purchase from you, if they move forward.

2. Don’t use Discovery on the Fly, except in the situations described below.

Cruising – Best Practices

Discovery on the fly is a very useful tool when applied in the right situations. Here are best practices and guidelines for when you should consider doing Discovery on the Fly and when it is not recommended:

  • Yes: for the initial portions of Vision Generation Demos;
  • Yes: for Vision Reengineering;
  • Yes: when the discussion segment is specifically about your software or you want to focus the discussion on your software;
  • Maybe: for transactional sales processes;
  • Maybe: when time is very limited;
  • No: other than the “Yes” items above, in any substantive discovery conversation.

Vision Generation Demos

In Vision Generation situations, your prospect is interested in gaining an understanding of what is possible with your software, occasionally phrased as seeing “the art of the possible”. This can generally be communicated quite rapidly: four to six minutes is sufficient to generate vision for a single solution.

Vision Generation Demo uses an appropriate Informal Success Story to align the prospect with other, similar customers who purchased your product (and are using it happily and productively), followed by sharing a few example key screens, often illustrating key outputs or deliverables.

It is designed to be just enough to satisfy the prospect’s desire to understand what is possible at a high level, and then to move the prospect into a real discovery conversation. Four to six minutes – that’s it.

Vision Generation Demos are constructed and performed with those two express objectives:

  1. Satisfy the prospect’s request for a demo;
  2. Move into discovery.

This is the essence of doing Discovery on the Fly: showing just enough product to enable a broader discovery conversation to take place. Once you have shared a few key screens, it takes strong personal discipline to keep from diving and driving…!

In Great Demo! methodology, we train vendor teams on the specifics of preparing and executing Vision Generation Demos. I generally recommend using static screens captured as screenshots unless there is substantial value in seeing the live software. This helps to reduce the risk of diving into your software and driving off on a painful Harbor Tour…!

Vision Reengineering

While prospects often engage with vendors fairly deep into their buying processes, their understanding of the solution space is generally limited to publicly available information. They don’t know what they don’t know and may be completely unaware of the possibilities in your offering.

Vision Reengineering is the process of filling those relevant information gaps in an elegant way.

A prospect who has been using Excel, for example, may be unaware of the additional options supported in modern dashboards. There is no “drill-down” capability in typical Excel workbooks, so a prospect may not immediately understand the ability to explore data by drilling-down several layers.

One picture is truly worth a thousand words. When you are working to reengineer a prospect’s vision of a solution, words can only go so far. Seeing a few example screens, with appropriate description, is often the best way to accomplish Vision Reengineering.

Note that Vision Reengineering typically happens after a great deal of discovery has been done. Demographics have been covered and the Major Pain has already been characterized, along with its Impact and Value. It is during the discussion of the Specific Capabilities that Vision Generation and Vision Reengineering come into the mix, and are done to move or expand the prospect’s thinking regarding your offering’s capabilities.

In this sense, it is also a Quid Pro Quo opportunity. You ask, “Would you like a few examples of what this could look like?” With a “Yes, please” response, you can show your software for those specific examples and screens, describing what your prospect is seeing, how they would use it to solve their problems, and the value associated with making the change.

In these cases, you may be showing output, dashboards or other deliverables, or sharing how a workflow is reduced, streamlined, or replaces existing processes.

The essence of Vision Reengineering is that your prospect is unaware of what is possible, and your job is to address that. The use of a few key screens from your software in your Vision Reengineering process is an appropriate application of Discovery on the Fly.

In Great Demo! training, we say, “One Illustration is worth a thousand mouse clicks…!”

Software Discussion Segment

This is a logical extension of Vision Reengineering. Your prospect has experience with a particular capability with their current implementation and might ask, “Well, how would this work with your software?”

And, like Vision Reengineering, your job is to answer the question with an appropriate brief demonstration of your software, and then get back to your discovery conversation. After showing and discussing the capability sufficiently, one effective way to do this is to close the lid on your laptop computer (or metaphorically close the lid, if you are working over the web by stopping screen sharing).

The key is to avoid the urge to dive and drive…

Transactional Sales Processes

If you are working to close a prospect in one or a few short calls and time is limited, you may consider using your software to help guide portions of the conversation. Again, it takes discipline to avoid showing too much software too early. The more time you spend showing your software, the less time is available for discovery. Discovery is done for both the vendor and the prospect!

Other Limited Time Situations

One can also make the case that in situations where time is limited, doing Discovery on the Fly with your software can be appropriate. When time is that limited, however, you are also at risk of shortcutting discovery and being perceived as being overly aggressive by your prospect. Your mindset in these situations should be to achieve a balance.

If the problem is important to solve for the prospect, it deserves sufficient discovery. If you run out of time on an initial call, suggest a follow-up call. Note that while you may have booked back-to-back-to-back calls and have run out of time for this meeting, you should not let that cut discovery short.

A simple rule of thumb is: the more complicated your offering, the more discovery is necessary. The converse is also true. Product-led offerings likely require less discovery, as prospects are often able to explore product-led solutions on their own through direct use.

Finally, by short-cutting discovery, you are allowing your competition to do a better job and establish a competitive advantage over you…! Your objective should always be to be perceived as doing a superior job of discovery versus your competition. It is a key differentiator.

Approach and Landing – Summary

Traditional presales and salespeople help their prospects solve and address their Major Pains; good presales and salespeople enable their prospects to address their Major and Related Pains; truly great sales teams build a long-term relationship with their prospects, with the goal to enable their prospects – as customers – to enjoy the most value possible over time.

Doing Discovery on the Fly often results in lost opportunities for both parties, by ignoring or not exploring the Impact and Value of Major Pain and/or Related Pains, as well as other Demographic, Environment, or Cultural factors that might affect implementation, adoption, renewals and expansion.

Use Discovery on the Fly carefully and wisely…!

Copyright © 2022 The Second Derivative – All Rights Reserved.

To learn the methods introduced above, consider enrolling in a Great Demo! Discovery or Demonstration Skills Workshop. For more demo and discovery tips, best practices, tools and techniques, explore our blog and articles on the Resources pages of our website at and join the Great Demo! LinkedIn Group to share your experiences and learn from others

Republished with author's permission from original post.

Peter Cohan
Have you ever seen a bad software demonstration? Peter Cohan is the founder and principal of Great Demo!, focused on helping software organizations improve the success rates of their demos. He authored Great Demo! - how to prepare and deliver surprisingly compelling software demonstrations. Peter has experience as an individual contributor, manager and senior management in marketing, sales, and business development. He has also been, and continues to be, a customer.


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