Stunningly Awful Discovery: The Dirty Dozen of Discovery Don’ts! - Great Demo

Stunningly Awful Discovery: The Dirty Dozen of Discovery Don’ts!

“It is better to ask some of the questions than to know all of the answers.”

– James Thurber


Here’s a collection of poor strategies, failed tactics, bad errors, and faulty discovery that increases the likelihood that your entire sales process will be a failure. I recommend that you avoid these!

If your discovery conversations are not as successful as you wish, consider using this list as an assessment tool. If any of these items occur frequently you may want to make some changes!

What “Don’ts” Are in This Article for You?

Bite-size or full meal learning: Your choice! You can sample each of these on their own or consume the full article. Either way, you win! Here’s the menu:

  1. Don’t do discovery at all.
  2. Don’t do enough.
  3. Use a “disco demo.”
  4. Make it an inquisition.
  5. Read questions from a long list.
  6. Do five minutes of discovery and then present your corporate or product overview.
  7. Do five minutes of discovery and then deliver your standard overview demo.
  8. Don’t communicate discovery info throughout the team.
  9. Ignore key elements that help you avoid No Decision outcomes.
  10. Don’t align discovery with job title.
  11. Don’t explore cultural attributes.
  12. Ignore poor solution “fit” and proceed with the sale.

Plus, a special bonus “Don’t!”

Each delightful “Don’t” also includes a solution to help you improve and avoid SAD (Stunningly Awful Discovery) outcomes. Enjoy!

The Stunningly Awful Discovery (SAD) Top Ten List:

1. Don’t Do Discovery at All.

Assume that all prospects are completely alike and have exactly the same needs, interests, and situations. While parts of this may be true (that’s what defines a market), this SAD assumption results in stunningly awful Harbor Tour demos, unnecessary POCs, numerous No Decision outcomes, and far-too-frequent losses to your competitors who actually do discovery!

Here’s an analogy of how ridiculous this is:

Imagine you feel very sick, and you head to the hospital. A doctor meets with you, but instead of asking any questions or performing any tests, they point you to the pharmacy and say, “Try each of the medications we have available and let me know if any work…”

That’s prescription without diagnosis, also known as medical malpractice!

Solution? Do discovery! Remember, discovery is done for both parties: to enable you as the vendor to propose a precise solution and to enable your prospect to feel confident that you have a sufficient understanding of their situation to be able to propose a precise solution.

2. Don’t Do Enough.

Far too many vendors simply identify “pain” and then launch immediately into proposing “solutions.” This is amusingly known as “premature elaboration,” and is nearly as bad as doing no discovery at all!

Many vendors confuse qualification with discovery. Once a prospect meets their qualification criteria, they are off to the solution and proposal races!

Even qualification can be insufficient (as every mature salesperson knows). Here are some unproductive qualification criteria for your amusement:

  • Marketing Qualified Lead: “Anyone who browses our website…”
  • Sales Qualified Lead: “Anyone who clicks the ‘Book a Demo’ button on our website…”
  • SDR Qualified Lead: “Anyone who agrees to a meeting with a salesperson…”
  • Inside Salesperson Qualified Lead: “Anyone on my outbound call list…”
  • Desperate Salesperson Qualified Lead: “Anyone with a heartbeat…”

In Doing Discovery, I identify seven levels of 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.

When vendor individuals honestly evaluate themselves, after digesting the definitions of each level, they typically place themselves at Levels 2 or 3. This leaves a lot of room for improvement!

Hospital Analogy: You arrive at a hospital and say, “I don’t feel well.” A doctor asks, “Where does it hurt?” and you reply, “My stomach…” The doctor announces, “This patient has stomach pain: Let’s get ‘em into surgery and open ‘em up right away!” (If I were you, I’d head for another hospital!)

Hospital Qualification Analogy: The doctor asks, “Do you have insurance?” to which you respond, “Yes, full healthcare insurance.” The doctor then immediately whisks you into surgery!

Solution? Define an example of what “great” looks like. One excellent approach is to generate a template based on a fully completed discovery document from a real prospect conversation that includes both the question prompts and the prospect’s responses. Optimally, it includes all the relevant portions of the full Doing Discovery methodology.

Two additional thoughts:

  1. The more complex the offering, the more discovery is needed.
  2. Prospects with complex problems want to be discovered, although they may push back until you’ve proven that you are worthy of their time. A Vision Generation Demo can be the solution to this! (See Chapter 11 in Great Demo!)

3. Use a “Disco Demo.”

“Disco Demos” or “Discovery on the Fly” are simply other terms for Harbor Tour demos, but where the vendor asks (over and over!), “Is this something of interest to you?” These are often inflicted on prospects in response to prospects’ requests to “just show me a demo!”

While the intent is to provide your prospect with examples of your offering and associated advantages, most of these demos devolve into a flood of features, resulting in very little useful discovery information and suffering from severe risk of Buying It Back.

Hospital Analogy: Imagine, again, you’ve headed to the hospital because you feel very sick. A doctor meets you at the entrance and, instead of asking any questions, they take you on a tour of the hospital. They show you the X-ray equipment and say, “We have a terrific, state-of-the-art X-ray system – is that something you might want?” and repeat that process for each department!

Solution? When possible, gently (but firmly!) convince your prospect of the value of doing discovery first, followed by a demo that focuses crisply on what was learned in discovery.

The doctor analogy can be an effective approach: “Before I offer a diagnosis and suggest a cure, I need to perform an examination…”

If your prospect still demands, “Just show me a demo…,” use the highly effective Vision Generation Demo method to satisfy your prospect’s desire to “see what’s possible,” while moving them comfortably into a discovery conversation: Win-win! (Chapter 11 in Great Demo!)

4. Make It an Inquisition.

This is a valid concern! Too many one-way questions can feel like an interrogation or inquisition.

Hospital Analogy: Imagine being handed a ten-page questionnaire that you need to complete before you can see the doctor, including line after line of detailed questions about your medical history, relatives, prescriptions, insurance, and on and on. Even worse, you don’t have answers to many of the questions, leaving you concerned that you’ll ever see the doctor at all!

Solution? While we need to be complete in gathering the information we require in our discovery processes, we must also offer information, guidance, and insights in return. Discovery needs to be perceived as a two-way conversation, where both parties each learn something new. In doing discovery, we accomplish this by offering quid pro quo comments, observations, and success stories.

These can range from insights into how other customers have addressed similar challenges, or even simple comments such as, “You are not alone…!” See the section on “Empathy and Quid Pro Quo” in Doing Discovery for more guidelines on this important practice.

Your prospect should feel that they also took away new and useful information from the discovery conversation. Again: Think win-win.

5. Read Questions From a Long List.

This is bad enough when inflicted over the web; it’s even worse when done face-to-face! The real issue isn’t the questions themselves, but rather the delivery. Reading verbatim from a script of questions is just painful for both parties.

It feels awkward, and it is!

True story: I was listening to a recorded discovery conversation and heard the vendor rep recite a long paragraph of a question that only yielded a “no” response from the prospect. There was a brief lull when the rep wrote down the prospect’s reply. And then the vendor launched another lengthy passage in question format that resulted in another “no” answer. This went on for nearly an hour! Boring, painful, and clearly an inquisition!

This approach stifles responses that might include more “color” and nuance, and it certainly suppresses the ability to make the call a real conversation.

Hospital Analogy: How would you feel if a doctor read long, detailed questions from a thick pad of paper or a tablet, one after another after another? It would feel uncomfortable rather quickly!

Solution? Know what you need to ask or use a “prompter” document. A prompter reduces the written questions down to a word or two, or brief word phrase. This ensures that you cover the discovery space necessary while enabling you to phrase the actual questions dynamically, using your own words. The result is a more natural delivery that spurs bidirectional, productive conversations.

6. Do Five Minutes of Discovery and Then Present Your Corporate or Product Overview.

I’ve watched and listened to hundreds of discovery calls and a very large percent suffer from this serious malady! It seems to be a result of (less mature) salespeople’s desire to “take control” and “present something.” In many SAD cases, presenting a corporate or product overview is considered a critical part of the vendor’s sales process.

Hospital Analogy: Imagine arriving at a hospital after suffering a bicycling accident. You are bleeding moderately, you hurt in multiple places, and you are concerned that you may have a broken bone or two. A doctor sees you, notes that you’re bleeding, and asks, “Where does it hurt?” and then starts a twenty-minute presentation covering the hospital’s mission statement, founding history, growth and revenues over time, patient statistics, departments and services… All the while you’re still bleeding, and the pain has only been made worse by suffering through the presentation!

Solution? Do discovery, not a presentation! This is the time to ask, not to tell!

7. Do Five Minutes of Discovery and Then Deliver Your Standard Overview Demo.

This is only slightly different from number 6 above, yet hundreds of vendors still plod unproductively down this pathway. Again, it appears to be driven by vendors’ urge to show and tell rather than ask and listen.

The results are as one might expect: prolonged sales cycles, frustrated prospects, multiple demos, unnecessary POCs and POVs, poor solution “fit,” and losses to No Decision and to competitors who do a superior job in discovery.

Remember: The vendor who is perceived by the prospect as doing a superior job in discovery is in a competitively advantageous position.

Hospital Analogy: Imagine arriving at a hospital after suffering a bicycling accident, as before: You’re bleeding, in pain, and concerned about broken bones. A doctor asks, “Where does it hurt?” After your brief response (“Everywhere…!”) they take you on (yet another) tour of the hospital, pointing out the wonderful equipment, staff, supplies, systems, and services available…

Solution? Put your offerings and your company “behind your back” in a virtual sense and engage in a fruitful, mutually beneficial discovery conversation. Then you’ll able to present a crisp, focused Technical Proof Demo that may eliminate the need for any further proof!

8. Don’t Communicate Discovery Info Throughout the Team.

As a prospect, imagine investing several hours in discovery discussions with a vendor, only to have the vendor ignore the information you provided. Instead, they show you features or entire modules you told them you aren’t interested in. They show you a list of hundreds of reports, but you only specified needing a handful. How would you feel? (I’d move on to another vendor who actually listens!)

Despite how incredibly insulting this is to the prospect, I see this happen far too frequently! Why does this happen? Several possible reasons:

  • Discovery information was not communicated within the selling team and the person or people delivering the demo resorted to their best guess or “standard overview” demo.
  • The person (or people) presenting the demo was told by management to include certain capabilities in every demo. These are often identified as “our key differentiators…”
  • Discovery information is habitually ignored in demos. Hard to believe, but it happens!

In complex sales involving multiple players from both the prospect and vendor, it is even more important to communicate effectively. Great Demo! Situation Slides are a terrific currency for passing discovery information from person to person and team to team.

Hospital Analogy: Regardless of the diagnosis, everyone in this hospital is treated for appendicitis!

Solution? Execute crisp and complete information handoffs between team members. Review and discuss discovery notes prior to any demo to reach agreement on what to show and what not to show! Bonus: Communicate that same information to your implementation/professional services folks and your customer success team!

9. Ignore Key Elements That Help You Avoid No Decision Outcomes.

According to Gartner (and many others), No Decision outcomes (also known as “Do Nothing” or “Status Quo”) comprise forty-five percent of forecasted opportunities. For many vendors, the number is even higher! Most vendors report that No Decision is their single largest competitor, yet very few vendors actively seek solutions.

Effective discovery that explores three key elements can dramatically reduce these No Decision rates. They are:

  1. The lack of a Critical Business Issue.
  2. Insufficient perception of value (insufficient Delta).
  3. No Critical Date.

Hospital (Patient) Analogies:

  1. “I can live with this pain… I don’t like it, but it’s not getting in the way of what I need to do.”
  2. “That drug/procedure is just too expensive… I’ll live with things the way they are.”
  3. “I’d prefer to put this procedure off until another time… Maybe next year.”

Solution? While there are many other reasons that could yield a No Decision outcome, including management or major business changes, economic challenges, etc., you can avoid overinvesting in many fruitless sales processes by doing discovery specifically for each of these elements!

10. Don’t Align Discovery with Job Title.

A salesperson colleague shared a sad story that offered a great lesson: Discovery questions and topics need to align with your prospect players’ job titles. Here’s his story:

“After a great deal of work, I finally got a meeting with an executive at a key prospect. I had my discovery template ready to go and launched into my questions as soon as the call began.

The executive’s initial responses to my questions were clipped: ‘I don’t know,’ ‘You’ll need to ask my team,’ ‘That’s an IT issue,’ and similar. I was getting nowhere, and the executive was losing patience.

Thankfully, he offered me some great advice, saying, ‘Listen. The questions you’re asking me should be asked of the team running the workflows, and of IT for the infrastructure info. I can give you guidance regarding the importance of our project, and our objectives and timeline. I can help you by delegating you down and introducing you to the right players.

In return,’ he said, ‘I need to you report back to me with your key findings. Let me know if you run into any roadblocks along the way.’

What a terrific person…! That exec helped me realize that my discovery questions need to align with each level and job title. Prospect staff members are highly knowledgeable about their specific workflows. Middle managers deal with short-term challenges, such as problem identification and team resource allocation. Execs offer insights into the overarching goals, objectives, projects, strategies, and timelines.

I was asking staff-level questions of executives and middle managers! Now I have several discovery templates, each aligned to my prospects’ specific job titles. And guess what? Now I’m making my numbers… No, I’m consistently crushing my numbers every quarter!”

Hospital Analogy: Don’t see a podiatrist about an ear infection, don’t ask a gastroenterologist to set a broken bone, and don’t seek a diagnosis from a hospital administrator!

Solution? Discovery is dependent on job title as this story illustrates. “Speeds and feeds” are workflow topics; strategy is a subject for executives. Remember that “pain flows downhill” and “solutions flow uphill!”

11. Don’t Explore Cultural Attributes.

Most vendors’ discovery questions focus on uncovering and understanding “pain,” and few examine impact and tangible value. But it is the rare vendor who explores cultural prospect attributes. These can provide a wealth of surprisingly valuable information!

For example, your prospect’s position on the Technology Adoption Curve is a leading indicator of the amount of proof they will require. Innovators may never need proof, for example, and a crisp demo can satisfy Early Adopters. Late Majority prospects, on the other hand, are likely to publish extensive RFPs and then require multiple demos, POCs, and POVs, and are still at risk of yielding a No Decision outcome!

Implementation strategies give another clue to culture. Do they prefer an initial test group followed by tuning, or rollout in waves, or all at once? How frequently do they onboard new applications? Do they embrace new technologies or avoid them? Do they perceive themselves as a leader or “fast follower?” Note that the age of their workforce may provide clues, as well.

Along similar lines, inquire about your prospect’s prospects! Companies that are most comfortable selling to the Late Majority are likely to have a similar culture.

Here’s an important cultural attribute: Organizations that have suffered a failed implementation or purchased a product that did not generate the expected ROI may be shy to pursue new solutions. They are “Burn Victims” who require additional investigation into “what happened?”

Hospital Analogy: Don’t go to a Catholic hospital if you are looking for an abortion!

Solution? Ask! Ask how they perceive themselves. Ask about their customers. Ask about their purchasing history and technology adoption habits. Ask if they’ve had a bad experience or suffered unsatisfactory performance with a prior purchase.

The information you learn may be extremely important in your sales process and in supporting your buyers’ processes!

12. Ignore Poor Solution “Fit” and Proceed with the Sale.

Have you ever purchased shoes or clothes that didn’t fit? Most likely they saw more closet time than their colleagues! Poor product or solution fit is a direct result of inadequate discovery (or worse, vendors who ignore what was learned in discovery and still push for the sale!).

Why does it happen? The more complex a prospect’s situation, the more likely it is that confusion takes place about vendor offerings. And the more vendors that a prospect explores, the more confused they can become: “Which vendor had the biframulator function? I can’t remember…!” This is aggravated by inaccurate or (ahem) devious answers to prospect questions and demos that make products look much better than reality.

What happens after the sale? If the fit is poor, the result will be a failed implementation or inability to achieve the desired objectives and ROI. This turns the customer into a Burn Victim, who won’t renew and will never buy from that vendor again!

While compensation drives performance, those of us who are solely compensated for “new name” sales still risk the impact of poor product fit. Each customer who churns because of inadequate fit is a negative reference and people who have suffered bad experiences tend to be vocal about them!

Hospital Analogy: Your insurance, which costs a bundle, didn’t cover your surgery, medications, or post-op care. The insurance company said, “’Life’ is a pre-existing condition, and we don’t cover that!”

Solution? Do detailed discovery, especially with respect to the Specific Capabilities your prospects need and the associated value. Analyze and apply a numeric scale for product fit measurements and back away from any opportunity where fit is below a rational threshold.

Bonus! Don’t Encourage Your Prospect to Go Off Script.

“Well,” said the salesperson, “We’ve covered all the questions on the list. Thanks for your time…”

The prospect had been contemplating revealing another, very important issue, but since the vendor was closing the meeting, the prospect player didn’t offer anything. Bad move, vendor!

Years ago, Steve Jobs was famous for casually remarking, at the apparent end of a presentation, “Oh, one more thing…” and then he’d reveal an amazing new product, feature, service, or concept.

Hospital Analogy: You’ve been discussing some gastrointestinal discomfort with your physician, who has prescribed an antacid medication. You are about to leave the examination room and, as your doctor’s hand reaches the doorknob to exit, you remark, “Actually, I’m kind of worried about a recurring headache I’ve been having. Can we talk about it?”

This is known as the doorknob effect, where patients are uncomfortable to reveal critical information until the last possible moment.

Solution? Here’s my favorite discovery question, used at the very end of your conversation: “Is there anything we haven’t discussed that we should be discussing?” This opens the (ahem) door for any additional non-structured information from your prospect. Try it!

A Bakers Dozen Don’ts

“The vendor perceived by the prospect as doing superior discovery is in a competitively advantageous position.”

– Me

Pursuing these twelve thirteen SAD practices will certainly increase the probability that your discovery conversations will fail to help you achieve your goals. Instead, of course, follow the “Solution” guidelines in each section to improve your results! Doing effective discovery is the key to crisper sales cycles, buyer enablement, and happy customers who renew and offer glowing references.

For a fun story that illustrates many of these concepts, enjoy reading A Prospect’s Tale.

Save yourself years! The Doing Discovery book and Workshops are time machines, compressing decades of learning, experimentation, improvement, and evolution into a few hours. You can acquire discovery skills the long, painful, hard way, or you can leverage this existing knowledge the fast, easy, effective way!

Is this the end of the list? Certainly not! Follow our blog and peruse our articles for much more discovery and demo do’s and don’ts!


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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.

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