Assessing Discovery Skill Levels – How Do You Rate? - Great Demo

Assessing Discovery Skill Levels – How Do You Rate?

assessing discovery skills levels

Assessing Discovery Skill Levels – How Do You Rate?

A Never Stop Learning! Article

“80% of my team believes they do a good job with discovery, but sadly they do not. They don’t know what they don’t know…!”

– Head of Sales


What’s in This Article for You?

  • Assess your discovery skills level
  • The impact of insufficient discovery
  • Discovery skills Levels 1-6 defined
  • The importance of methodology
  • And a medical analogy sprinkled throughout!


Initial Assessment

Many sales and presales practitioners say they are skilled at doing discovery, but are they? Are you? Here’s a simple method to assess, based on seven levels of increasing proficiency:

  • Level 1: Uncovers statements of pain.
  • Level 2: Uncovers pain and explores more deeply.
  • Level 3: Uncovers pain, explores deeply, broadens the pain, and investigates the impact.
  • Level 4: Uncovers pain, explores and broadens, investigates impact, and quantifies.
  • Level 5: Uncovers pain, explores and broadens, investigates impact, quantifies, and reengineers vision.
  • Level 6: Applies these skills to the broad range of prospects represented across the Technology Adoption Curve, “burn victims,” disruptive and new product categories, transactional sales cycles, and other scenarios.
  • Level 7: Integrates and aligns the skills above into a cohesive discovery methodology.


The Impact of Insufficient Discovery

Insufficient discovery is the leading cause of a multitude of addressable sales process errors and failures.

For example, typical SaaS software vendors suffer No Decision rates at an average of 45% of their forecasted opportunities. That’s nearly half of the sales projects worked on each year that go … nowhere!

Similarly, vendors report that roughly 30% of all demos delivered were “wasted,” largely due to a lack of discovery. These are frequently “overview demos,” delivered to satisfy prospects’ desires to “see what’s possible.” (See Chapter 11 “Vision Generation Demos” in the Third Edition of Great Demo! for a delightful and effective cure to this problem.)

What is your current No Decision rate? What percent of your demos are wasted?

Overall, consider how many demos, POCs, POVs, and other sales activities have been executed – and failed – as a result of inadequate discovery. Consider how much discounting has occurred when vendors “Buy It Back,” another result of deficient discovery. Then include the number of customers who have churned due to poor product fit, along with the negative references that those generate.

The costs are staggering!

When most vendor customer-facing staff are asked about their discovery skills levels, they frequently picture themselves at Levels 3 to 4. However, when their management characterizes their teams’ performance, the results are frighteningly low: Levels 1 or 2. This disparity indicates that the Dunning-Kruger effect is in play: Sales and presales practitioners “Don’t know what they don’t know” about doing discovery!

Let’s take a deeper look and see where you stand…


Level 1 – Uncovers Pain

When doing discovery, if you simply uncover “pain” and go no further, then you are a novice.

For example, the prospect offers, “Our current process is manual…” Many vendors leap to propose a solution at this point: This is Level 1 discovery.

Very basic, clearly insufficient, and it leads to all of the negative outcomes described above!

[Let’s use a medical analogy to illustrate these ideas as we develop them. Imagine you go to see a doctor because you have a pain in your side that concerns you. At Level 1, the doctor simply says, “Take an aspirin.” In medicine, we’d call this malpractice!]


Level 2 – Explores Pain More Deeply

Vendor representatives with slightly stronger discovery skills ask follow-up questions to explore prospect pain more deeply.


The prospect says, “Our current process is manual…”

Vendor replies, “Sorry to hear this – why is this an issue?”

Prospect responds, “Well, it takes too long to get the reports we need and there are often errors in the reports…”

This shows a step up in skills attainment: Level 2. The pain description is a bit deeper and the impact is beginning to be understood, but we can go much further. And again, this level of discovery yields the same troubled results.

[In our medical analogy at Level 2, the doctor asks you, “Where and how badly does it hurt?” Again, wholly insufficient!]


Level 3 – Investigates the Impact

Practitioners at Level 3 seek to understand more about the impact of the pain on the immediate and extended prospect organization. Let’s revisit the conversation:

The prospect says, “Our current process is manual…”

Vendor replies, “Sorry to hear this – why is this an issue?”

Prospect responds, “Well, it takes too long to get the reports we need and there are often errors in the reports, because of the manual process…”

Vendor asks, “What’s in these reports and how is it used?”

Prospect answers, “Well, the reports give us visibility into where we have problems to address. When the reports are late – which is nearly always – the delay results in unhappy internal customers…”

Vendor replies: “Oh, I see – who are your internal customers and how do they use those reports?”

This conversation continues, exploring the content of the reports, how they are consumed, the nature of the problems, how the user population is impacted, and how addressing the process impacts the prospect’s goals and objectives.

This discussion broadens and deepens the exploration of the pain and looks beyond the immediate workflow. Who else is impacted and in which departments? Is this a local problem or something that affects the organization more extensively?

Level 3 is all about understanding impact.

[Returning to our medical analogy, at Level 3 the doctor explores your pain significantly further, asking, “Does this keep you from doing any activities, such as exercise, or driving, or impact your ability to work?” Note that this drives a real conversation!]

Where can we go from here? To uncover tangible value!


Level 4 – Quantifies

This is where Dunning-Kruger often comes into play. Many customer-facing team members think they have “uncovered value” from their prospects, but far too frequently that value information is qualitative and not quantitative. Their prospects tell them, “We need this to be done better” or “faster” or “less expensively,” but the opportunity never seems to close.

Why does this happen? It’s because prospects cannot build a business case to justify a desired purchase without concrete numbers!

Many years ago, as a young product manager, I needed to buy a software tool to track and manage feature requests and release plans. That tool cost about $60,000, a significant investment for our company. It was clear to our team that we needed this solution, as we had been suffering serious challenges that were impacting our business. I went to our CFO with the purchase request and he denied it, saying, “Cohan, you need to build a compelling business case for this. Simply saying ‘you need it’ won’t fly!”

He continued, “Part of my job is to determine the best investment for that $60K. Right now, I’d do better to put it into Treasury Notes or similar, since the yield over the next couple of quarters is about 5%. You have shown zero yield with your proposal…”

“Ohhhhh…” I thought (along with a few other, non-printable thoughts), and I went back to my desk to produce an ROI analysis that showed breakeven within six months and a four-fold return within a year. He approved the purchase!

At Level 4, presales and salespeople quantify the pain, using the prospect’s own numbers. For example:

Vendor says, “You noted that it takes too long to get these reports done – how long is it taking today?”

Prospect responds, “Oh, it takes about a week – 5 working days…”

Vendor asks, “How long would you like it to take – or need it to take – to feel you’ve really addressed this problem?”

Prospect answers, “Well, if we could get these done accurately in a half a day, that would be terrific…!”

Now we have a tangible Delta of value, the difference between the prospect’s current state and their desired future state, of 4.5 days. The vendor should explore this further by asking how often the reports are generated, how often errors occur (and what happens when they do), and how much time is consumed by the team creating these reports.

The answers to these questions might result in the following exchange:

Vendor summarizes, “So, if I understand correctly, generating these reports is currently consuming nearly three FTEs annually, and taking four and a half days longer than you want, which impacts the organization’s decision-making and downstream results. In addition, it is causing below-desired internal NPS numbers for you and your team.”

Prospect responds, “That’s correct – and I hadn’t really internalized the full cost of this problem until now…!”

This information provides the inputs necessary to build the prospect’s business case to support the purchase. You can’t create a compelling business case just based on “we’ll do this faster” or “it’ll cost less”: You’ve got to quantify it!

Level 4 skills are all about uncovering tangible value.

[Back in our medical analogy, note that doctors will frequently ask you to quantify the degree of pain on a ten-point scale.]

Can we do better than this? Absolutely…!


Level 5 – Reengineers Vision

What is vision reengineering?

Consider: Do your prospects know everything about your offerings’ capabilities? Are they aware of all of the possibilities?


It is highly unlikely that a vendor will list (and successfully communicate) the full range of their products’ features, functions, and deliverables publicly. Traditionally, they attempt to provide these descriptions via long, torturous, traditional demos, which fail to accomplish the desired goals of education and competitive differentiation. Instead, they suffer from Buying It Back and sad stories such as A Prospect’s Tale, in addition to making the vendor’s software look complicated, confusing, overwhelming, and expensive.

So, how do you communicate capabilities that your prospects are unaware of, without the risk of a “show up and throw up” approach? Practitioners at Level 5 reengineer the prospect’s vision of a solution.

In our conversation from above, our vendor asks the prospect to share an example of the report currently used. After viewing the report, the vendor realizes that it lacks certain capabilities or possibilities, and explores these with the prospect:

Vendor notes, “It looks like you have a good basic view of what’s working and what’s not in these reports, but they are static, if I understand correctly. Would it be useful or interesting to be able to drill down to find the root causes, right from the report?”

Prospect responds, “Wow, yes that would be terrific – that would save a lot of time…!” [How much time savings might also be explored here…]

Our vendor has now proposed an improved version of the report and the prospect has agreed this would be better. This is one example of Vision Reengineering: Going beyond the prospect’s initial vision of a solution.

The ability to execute this kind of Vision Reengineering is a Level 5 skill.

[Returning again to our medical analogy, let’s assume that your doctor has accurately diagnosed the problem behind the pain in your side. She notes, “Traditionally, your issue is addressed through surgery that requires a few days in the hospital. However, there’s also a newer non-invasive alternative to consider, based on radiofrequency techniques that has been producing improved outcomes. Many of my other patients, in very similar situations to yours, found that this technique yielded superior results with less hospital time. Is this something you might also want to consider?”

Note the delightful use of a Biased Question here…! Biased Questions are an elegant, effective way to execute Vision Reengineering. Details can be found in the “Elements of Discovery” section of Doing Discovery.]


Level 5 with a Differentiating Twist

Vision Reengineering is also an opportunity to outflank competition.

In our example conversation, our vendor realizes that they have a relevant capability that is not matched by the competition and introduces it as follows:

Vendor notes, “Many of our other customers, in similar situations to what you’ve described so far, found it very useful to have these reports sent automatically to their consumers via an email link – but only when there was a problem to be addressed. Our customers report that they didn’t waste time reviewing reports where there were no issues. In some cases, they reported saving several hours every week. Is this a capability that you’d also like to have?”

Prospect answers, “Wow – yes, that would be really helpful for us as well…!”

Vendor offers, “Great – let’s plan to include it in the demo…”

Here, our vendor rep has introduced the alert-based capability, a key differentiator, and turned it into a Specific Capability that the prospect wants and expects in a solution.

The folks at Level 5 not only reengineer vision but also competitively outflank.

[While one would hope that hospitals are all about patient outcomes, they are also businesses. According, let’s listen in as your doctor continues, saying, “By the way, we are the only hospital in the region with the facilities that offer the radiofrequency option…”]


Brief Digression

So far, we’ve outlined a subset of discovery skills to provide you with an easy mechanism to assess your overall level. There are many other skills not addressed in this simple ranking system, including starting discovery, managing timing and flow, probing methods, workflow analysis, going beyond the workflow, individuals vs groups, dealing with executives, “Why” questions, culture and uniqueness, and more.

[The same is true in medicine. Consider how long it takes for a person, even after earning a medical degree, before they are allowed to practice on their own!]

The take-away is simple: There’s much more to learn than what is represented in the five skills levels defined so far! Which takes us to…


Level 6 – Other Scenarios

Many vendor organizations generate lists of discovery questions designed for their “standard” prospects. Sadly, the reality is that there is no such thing as a “standard” prospect! While many prospects fit within a reasonable range of situations and experiences, there are numerous examples that extend well beyond the norm.

These include “burn victims,” prospects on different portions of the Technology Adoption Curve, prospects for disruptive and new product categories, experienced vs first-time buyers, working with the C-Suite, transactional sales cycles, and many more.

[In medicine, in addition to the current complaint, doctors need to know about pre-existing conditions, medications, family history, age, environment, and many other factors to accurately diagnose and treat your specific situation.]

Software buyer “burn victims” offer a good example to explore…


Burn Victims – Fear and Loathing of Risk Unrewarded

“Have you tried to fix this before?” Answers to this question can yield interesting and sometimes surprising information.

Prospects who attempted to address problems previously and failed are known as “burn victims” and they tend to be very careful about subsequent solution proposals!

A “yes” response to the question above requires careful follow-up. “What happened?” is a good starting point. You need to understand what actions were taken, what tools were purchased, what was implemented, when this all took place, and what the outcomes were for the individual, as well as the organization and others who were impacted.

There is great risk in change, often accompanied by fear and loathing. And for good reason!

Have you ever seen an implementation effort fail? Have you ever met a prospect who was unable to gain the desired value from a purchase? Have you ever encountered someone who had to roll back to a previous solution?

In discovery conversations, you need to determine if your prospect is a burn victim and then explore exactly what happened. Gaining clarity as to why this all happened is an overarching objective. Only by hearing and understanding your prospect’s sad story can you convince them that the same thing won’t happen with you as the vendor!

[“I’ve been to several doctors and hospitals so far, without success…”]


Discovery Across the Technology Adoption Curve

Another set of example scenarios is evident in the range of individual and corporate personalities associated with different positions on the Technology Adoption Curve. Innovators tend to require very little discovery: They often synthesize use cases on their own! Early Adopters are similar, but typically want a reasonable level of discovery to confirm their own opinions.

Early Majority prospects differ, sometimes greatly, from Late Majority players in the level of proof required and with the corresponding amount of discovery. Whereas Early Majority individuals may be satisfied with a Technical Proof Demo, as you move to the right with that population on the curve, they’ll start to require POCs. Late Majority players are much more likely to pursue an RFP process (And even further to the right you can expect to receive an RFI followed by an RFP. Sadly, even after all of this work, there is a high probability that the entire effort will end in a No Decision outcome!).

Laggards may never make a change and no amount of discovery will satisfy!

[Consider the medical situation where the patient says, “Well, I’ve had this pain in my side for years and I’m used to it. Even though it hurts, I’m more comfortable just dealing with it than risking surgery or some new procedure…!”]

For another Level 6 example, consider transactional sales processes, where opportunity size is small and interactions with prospects are brief. These scenarios require yet another version of discovery (and demo) skills. See our article for the full story.

Level 6 practitioners are adept at applying appropriate questioning and probing methods, plus application of these skills to the special circumstances of the “non-standard” population.

What’s next?


Level 7 – Discovery Methodology

The skills discussed so far are just that: individual skills. The next logical question is, “When and how should these various skills be applied?”

Should a discovery conversation begin with “establishing rapport” vs directly exploring pain? When can you transition from diagnosing prospect pain to discussing a solution? Are there best practices for timing and flow? How do you change topics; when do you employ Expansion Questions to dig deeper; what are good quid pro quo to offer along the way; how do you know you’ve covered enough?

And how do you, as an organization, ensure that the output of your discovery conversations is consistent within your team? How do you avoid CRM discovery notes from untrained reps that consist of, “It’s a huge opportunity”?

The answer is that discovery must be perceived as an integrated, cohesive methodology, where the individual skills are applied in a structured, repeatable process.


Another Analogy: Let’s Build a House!

While our medical analogy might still be appropriate to illustrate some of the key concepts of methodologies, we’ll change to something a bit more, ahem, concrete!

Contemplate a range of construction skills: the ability to hammer nails, drill holes, saw wood, pour cement, connect wiring, plumb sinks and drains, install drywall, paint, etc. Each of these skills takes time to learn and master.

Building a complete house requires these skills and coordinated timing and flow.

In order to know what to build, an architect generates plans. A full set may include separate sections for the foundation, framing, plumbing plan, electrical and lighting, heating and cooling, roof and exterior, interior finish, cabinetry and fittings, and more.

The contractor takes the plans and coordinates the timing and flow of each step: That’s the methodology of construction! You can’t install light fixtures and electrical wiring until the framing is in place, but you also need to do the electrical before installing drywall and finish.

Imagine the disaster if a concrete foundation is poured and then the contractor realizes that plumbing and electrical conduits should have been installed first…!

[How would you feel if, after you report a pain in your side, the doctor says, “Well, let’s just open you up and see what we find?” (Run away…!)]

Methodology is what coordinates the individual skills with the correct timing and flow.


Level 7 – Discovery as a Methodology

Construction contractors work from sets of plans to know what needs to be built. Over a period of years, they have acquired the knowledge to lay out the timing, assemble the appropriate skilled workers as needed, and direct them. (There are numerous books that lay out the process: A quick search on Amazon yields dozens.)

Similarly, seasoned sales and presales practitioners with many years of experience may have synthesized their own personal discovery methodologies, but each will have strengths, weaknesses, gaps, and additions based on their personal experiences. What is needed is an organizational discovery methodology: that’s Level 7!

This means that vendor teams need discovery outlines or templates predefined with recommended flow and timing. A completed discovery document for a prospect is the output of the process and such completed discovery documents should look similar from sales rep to rep and presales practitioner to practitioner.

A successful discovery methodology works comfortably for both the prospect and vendor. At the end of the conversation(s), the prospect feels fully “heard” and the vendor feels fully enabled to propose a precise solution.

An assessment for Level 7 includes two “figures of merit”:

  1. Your organization executes skills at Level 5 at minimum (and at Level 6 for the typical range of prospects you encounter).
  2. You consistently capture and document the complete set of discovery information necessary to propose precise solutions, and implement and enable your customers to achieve the agreed-upon value.

(Hint: If your Customer Success team is confused or unclear about your new customers’ goals, use cases, and success criteria, based on your internal documentation, you definitely aren’t at Level 7!)

[In your visit to the doctor, note the methodology applied to diagnosis: You started in the waiting room (or online) to complete forms capturing your medical history, medications, and related information. You then had your “vitals” taken and recorded (temperature, blood pressure, pulse rate, weight) prior to seeing the physician. The diagnostic process may have also included blood analysis, MRI, X-ray, or other tests. Finally, your doctor may have called on colleagues to assist in diagnosis, as well. Methodology is applied at each step and across the entire process (hopefully)!]


Seven Skills Levels for Doing Discovery


Level 1: Uncovers statements of pain.

Level 2: Uncovers pain and explores more deeply.

Level 3: Uncovers pain, explores deeply, broadens the pain and investigates the impact.

Level 4: Uncovers pain, explores and broadens, investigates impact, and quantifies.

Level 5: Uncovers pain, explores and broadens, investigates impact, quantifies, and reengineers vision.

Level 6: Applies these skills to the broad range of prospects represented across the Technology Adoption Curve, “burn victims,” disruptive and new product categories, transactional sales cycles, and other scenarios.

Level 7: Integrates and aligns the skills above into a cohesive discovery methodology.


Now that you’ve explored this far, reassess. How do your discovery skills compare?

(Contact us if you’d like to explore implementing Doing Discovery skills and methodology at your organization…!)


Copyright © 2021-2023 The Second Derivative – All Rights Reserved.

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

Scroll to Top