Neil Rackham’s research suggests that the quality of discovery—what he calls Investigating—is the clearest behavioral difference between top performers and everyone else.
Over and over again we’d find that salespeople who were described by their managers as ‘weak closers’ were, in fact, unskilled in Investigating.
— SPIN Selling, Neil Rackham
Across forums, sellers describe discovery as one of their main challenges—and I have seen it as one of the most common shortcomings, both as a sales leader and as a rep.
Why Discovery Matters in Enterprise Sales: Deal Quality, Urgency, and Trust
Discovery decides deal quality because it sits at the front of the commercial value chain. John McMahon describes enterprise selling as a sequence that starts with Discovery and only later moves into scoping, Economic Buyer alignment, validation, and business-case/proposal work. Discovery does not “support” the deal. Discovery creates the deal.
McMahon sequence (for orientation): Discovery → Scoping → Economic Buyer Meeting → Validation Event → Business Case/Final Proposal → Negotiate/Close.
— The Qualified Sales Leader, John McMahon
Discovery is the point where a seller earns the right to proceed by:
- Clarifying the customer’s use case and current state
- Translate problems into consequences
- Translate consequences into business outcomes and metrics
- Identify the people who own the problem and the path to a decision
The good news about discovery is that, although some people listen well because they are naturally curious, everyone can learn the skill because proven frameworks exist and deliver strong results.
Personally, I am highly curious—learning and individualization are two of my core strengths—but I also lean introverted. Because of that, I had to work deliberately on how I show up in discovery. A framework that I could use, that I trusted, and that helped me serve customers better became foundational.
SPIN calls this stage Investigating and treats it as the most important capability in larger sales because it turns implied needs into explicit needs.
The Challenger lens adds a second layer: strong discovery does not only reveal what the buyer already knows. Strong discovery often teaches a better frame, which improves the buyer’s clarity and decision quality.
Finally, discovery is not only information gathering. Discovery is trust building. Without trust, you do not hear the real story.
Command of the Message is a third example for a framework, that makes this practical because it gives you a repeatable way to turn what you hear into a decision-grade narrative. It combines the Current State with the Negative Consequences, then contrasts both with the customer’s Future State in the form of clear Goals and Positive Business Outcomes. It then bridges the gap through Required Capabilities and Metrics, so that the customer can evaluate options and justify action internally.
Before we go into the details, we should look at the real-world challenges that show up repeatedly in discovery. This article is supposed to help you orient yourself. Look for the challenges you or your team faces. You will find a short summary, first ideas, as well as links to in-depth materials to help solve this problem.
In the last section, I have provided an overview of the core frameworks you can use for discovery.
Common Discovery Challenges in Sales: What Reps Struggle With
Discovery fails in predictable ways. Reps compress too much into too little time, rely on generic question lists, and then either stay at surface-level pain or jump into product too early. In complex deals, they treat one stakeholder as a proxy for the whole organization, which leaves decision dynamics, metrics, and urgency undefined.
The insights in this article come from three sources. First, they come from recurring patterns that show up in public discussions, especially in r/sales threads and similar forums, where reps describe their real struggles in plain language. Second, they come from established discovery frameworks such as SPIN Selling, The Qualified Sales Leader, The Challenger Sale, and Command of the Message. Third, they come from my own experience, both as an individual contributor and as a leader, where the quality of discovery repeatedly predicted pipeline health and win rates.
What Is a Discovery Call? Definition, Scope, and Meeting Intent
People talk about discovery without defining it.
- Some reps call a first call “discovery” while they actually run a product tour.
- Some teams label every early call “discovery” even when the buyer expects qualification or a working session.
- Buyers resist the label “discovery call” because they anticipate a seller agenda.
Result: expectations diverge, which breaks sequencing and control.
Source threads
- How the hell do you do discovery in 30 minutes?
- Disco Wednesday — favorite discovery call questions & tactics to nail the pain
Discovery in 30 Minutes: Structuring the Call Without Stage Confusion
People treat a 30-minute slot as a container for everything: rapport, agenda, discovery, qualification, a demo, and next steps. The core problem is not time. The core problem is stage confusion: reps try to do discovery, scoping, and business-case work in a single sitting.
In one-call transactional sales, that compression can work because the product is simple and the customer can decide immediately—so the call ends with a purchase, not with “next steps.” In discovery-led sales, the meeting has a different intention: it should produce clarity, alignment, and a concrete next step that matches the buying process.
SPIN warns that top performers build needs before they move into value articulation. When reps compress the sequence, they often jump into solution talk at the first signal of need.
Source threads
Why Discovery Feels Awkward: Confidence, Silence, and Asking Hard Questions
People experience discovery as awkward for three recurring reasons:
- They fear silence
- They fear “difficult” questions
- They fear that probing will feel confrontational
McMahon’s framing helps: the seller must create an environment where it becomes easier to explore deeply and to ask difficult qualifying questions.
It’s our job to create an environment where it’s more pleasurable for reps to ask the customers the difficult qualifying questions, explore deeper during Discovery, and examine the details during Scoping.
— The Qualified Sales Leader, John McMahon
This is a facilitation skill. Multipliers calls this Create Space: shift the ratio of listening to talking and define a space for discovery.
Shift the ratio of listening to talking. Define a space for discovery. Level the playing field.
— Multipliers, Liz Wiseman
Source threads
Discovery Questions: From Question Lists to a Structured Learning Plan
People hunt for question lists because they lack an internal model of:
- What they must learn
- In which order
- For which output
Great sellers start one level higher than “questions.” They understand the process that they want to take customers through. They understand the value that each stage creates for the customer. They then design the questions that belong in each stage, so they can qualify whether it makes sense to proceed. SPIN makes this practical because it treats questions as a sequence that moves the buyer from context → problem → implication → explicit need. When people ask for “the best questions,” they often seek certainty while they avoid sequencing and intent.
Source threads
- Disco Wednesday — favorite discovery call questions & tactics to nail the pain
- What Questions do you find the most success with in your discovery process?
- What discovery questions do you think EVERY sales rep in ANY industry MUST ask?
Getting to Real Pain: Implication, Quantification, and Metrics
This is the most common failure mode.
John McMahon states it directly: many salespeople find pain; fewer quantify it; only a small minority implicate it. Without quantified pain, price lacks justification. Without implicated pain, urgency never forms.
Some salespeople will find pain, but fewer salespeople quantify pain, and only a small minority will ever implicate pain. If salespeople never quantify pain, they can’t justify their price point. If salespeople never implicate pain, they never create urgency.
— The Qualified Sales Leader, John McMahon
SPIN describes the same dynamic using different language: implied needs stay shallow until implication makes them serious and need-payoff makes them explicit.
At senior levels, pain typically expresses itself as revenue, profitability, or risk. If discovery never reaches these dimensions, the deal stays fragile. This is also why the collection of metrics is critical, because metrics translate pain into decision-grade evidence. If you want a deeper breakdown, see my article: MEDDPICC Metrics – How Metrics Are Discovered, Qualified, and Used Across the Sales Process.
Source threads
- Disco Wednesday — favorite discovery call questions & tactics to nail the pain
- How the hell do you do discovery in 30 minutes?
Multi-Threaded Discovery: Stakeholders, Champions, and Economic Buyer Access
People struggle because they treat discovery as a one-person conversation.
In reality though, most complex sales involves many different perspectives. You have users who touch the product every day. You have stakeholders whose processes are directly impacted. You have downstream customers who experience a different level of service as a result. You have sales, operations, and finance leaders who measure impact differently.
To understand what your product and service can actually do for them, you need to talk to these different groups. If you use the interaction with one person as a proxy, you will miss the real picture, because that person does not fully know how others experience the challenges, how they express them, and how they measure them.
All this is often shortened as:
- Find pain
- Pain finds Champion
- Champion enables access to the Economic Buyer
The consensus sale isn’t something you should be fighting — it’s something you should be actively pursuing.
— The Challenger Sale, Matthew Dixon & Brent Adamson
When access to key stakeholders stays blocked, the probability of winning collapses. Challenger treats early stakeholder access as a litmus test for whether to continue.
If you want a deeper breakdown, I cover both roles in my MEDDICC series:
Source threads
Qualify Early Without Being Shallow: Disqualifying Fast in Complex Deals
People ask how to disqualify fast because time waste is real. Disqualifying late wastes time because it consumes scarce resources on both sides—calendar slots, preparation, internal alignment, and leadership attention—without increasing the probability of a successful outcome.
For the rep and the selling organization, late disqualification creates forecasting noise, distracts teams from stronger opportunities, and drains credibility when a basic blocker shows up late. For the customer, late disqualification wastes time, reduces perceived value of the interaction, and can damage trust in the brand—especially when stakeholders feel that meetings served the seller more than the buyer. In the worst cases, that perception becomes visible in internal feedback, procurement skepticism, or public reviews.
Because the damage compounds over time, early disqualification becomes a form of customer service, not only a form of rep efficiency.
The hidden problem is that people either
- Disqualify based on shallow signals
- Keep working without a clear definition of what must be true to progress.
At this point, MEDDICC helps as a practical qualification framework because it forces early clarity on the fundamentals. First, you qualify Pain until it becomes implicated and measurable. Second, you qualify whether a Champion exists who will drive the initiative internally and earn you access to the Economic Buyer. You then build the rest of the deal on top of that foundation, instead of guessing.
For the full framework, see: Deal Qualification in Sales – MEDDICC.
For the core roles, see:
Source threads
Discovery Call Control: Agenda, Time Boxes, and Concrete Next Steps
People lose control when they:
- Skip a mutual agenda
- Avoid time boxes
- Accept vague endings
SPIN offers a forcing function: plan for an objective that results in a customer action. Seek an Advance, not a continuation.
Source threads
- Establishing clear NEXT STEPS in sales?
- How do you deal with prospects who take control/power of …
- I read many SaaS Discovery guides so you don’t have to
Pre-Call Preparation: Hypothesis-Driven Discovery and Research Discipline
People enter discovery without a point of view and then compensate with generic questions.
Christensen’s “discovery-driven” logic applies: you should state the assumptions that must prove true. Otherwise you run random exploration.
Source threads
- How do you research your prospect pre-call?
- Blew a discovery call
- I’m absolutely stumped by this interview question and I need help
From Discovery to Business Case: Turning Inputs Into a Decision Narrative
People collect facts and still lose.
They fail to synthesize the story into:
- current state,
- negative consequences,
- future state,
- measurable outcomes,
- required capabilities,
- proof.
McMahon’s Economic Buyer meeting summary mirrors this structure and sets the standard: discovery becomes valuable when it becomes a coherent business story.
Source threads
- What are the actual qualities and skills of a good sales rep?
- Everyone talks about “providing value” to prospects during …
- Sales Objection Handling Challenge: “The Budget is Locked”
Handling Product Pull: Avoiding Premature Demos and Feature Traps
People get dragged into demos too early.
SPIN documents a common pattern: when customers raise needs, sellers respond by talking about solutions. That move reduces learning and prevents the buyer from stating explicit needs.
Source threads
- Early in discovery, prospect says “we need feature x
- What’s a ‘red flag’ during a discovery call that instantly tells …
- Share your killer discovery/demo questions here
- When in your demo do you typically present price?
Enterprise Deal Friction: Security, Legal, Procurement, and Process Risk
People discover friction late and then misread delays as “stalled deals.”
McMahon lists complexity factors that predict friction early: multiple stakeholders, multi-level decisioning, and legal/procurement processes.
Champions, as McMahon defines them, do not only like you. Champions sponsor the path through procurement, legal, and internal justification.
Source threads
- Let’s talk about Enterprise Software Sales (Fasted way to …)
- What’s the meta with Enterprise sales in 2025?
- Closing Stage of Deal – How to win?
- How to assess Talent independent of Territory AND Timing?
What Great Discovery Covers: A High-Level Map Without Scripts
Command of the Message Discovery Spine: Current State to Outcomes via Requirements and Metrics
Great discovery follows a spine that produces a business narrative.
- Before Scenario (current state)
- Negative Consequences (cost of inaction)
- After Scenario (desired future)
- Positive Business Outcomes (measurable wins)
- Required Capabilities (requirements in customer language)
- Metrics (definition of success)
- Later: How we do it / proof points — only after the above exists
McMahon’s “be immersed in customer conversation” list fits into this spine, because each item maps to a concrete discovery output.
- Use case: what the customer is trying to accomplish, where it lives in the business, and what “good” looks like.
- Typical pains in the use case: what usually breaks, which constraints show up, and where the current approach fails.
- Open-ended discovery questions: questions that surface the buyer’s language, assumptions, and decision drivers.
- Differentiators: what is meaningfully different about your approach, relative to alternatives.
- Differentiators that solve pain: the explicit linkage from capability → requirement → pain reduction.
- Quantifiable value: baseline metrics and the measurable upside or risk reduction in the customer’s terms.
- Success stories with before/after scenarios: proof that reinforces the narrative (current state → consequences → future state → outcomes).
McMahon’s “3 Whys” maps onto the same structure:
- Why do anything? (pain level above the noise)
- Why do they have to buy? (who is impacted, what measures)
- Why us? (differentiators tied to pains)
- Why now? (what happens if they do nothing)
Challenger’s role-based “cards” strengthens the People dimension: for each stakeholder, define KPIs, concerns, and value levers, and map them to capabilities.
SPIN Selling for Discovery: Question Sequencing That Produces Explicit Needs
SPIN is a separate discovery framework. It does not replace Command of the Message. It complements it.
Command of the Message gives you the narrative structure: Current State → Negative Consequences → Future State → Positive Business Outcomes, bridged by Required Capabilities and Metrics.
SPIN gives you the questioning sequence that reliably produces the inputs for that narrative.
A practical way to combine both:
- Use Situation and Problem questions to build the Current State and to surface what breaks today.
- Use Implication questions to deepen the Negative Consequences until the cost of inaction becomes clear.
- Use Need-Payoff questions to let the customer articulate the Future State and the Positive Business Outcomes in their own words.
The purpose of questions in the larger sale is to uncover Implied Needs and to develop them into Explicit Needs.
— SPIN Selling, Neil Rackham
Use SPIN as a disciplined way to get to the spine, because it prevents two common errors: collecting context without meaning, and pitching solutions before needs become explicit.
A-Player Discovery Disciplines: Habits That Build Trust and Deal Momentum
What a Discovery Meeting Is: Definition, Outputs, and Next-Step Criteria
A discovery meeting is not “a chat.” A discovery meeting is a decision-oriented working session whose goal is not to sell anything, but to understand whether meaningful challenges exist and whether they are relevant enough to justify the next step.
- A discovery meeting is a structured conversation with a new or newly engaged stakeholder who matches the ICP.
- The intent is to gather specific, pre-defined information that lets you identify and validate a new opportunity.
- The output is a clear go/no-go signal and a crisp hypothesis about: Project, Pain, People, and the next decision step.
McMahon’s flow of customer conversation describes the behavioral standard:
- Questioning → Listening → Confirming → Feeling.
SPIN adds planning discipline: include objectives that result in a specific customer action; seek advances, not continuations.
Trust in Discovery: Using the Trust Equation to Improve Credibility and Reduce Self-Orientation
Trust = (Credibility + Reliability + Intimacy) / Self-Orientation.
— The Trusted Advisor, David H. Maister, Charles H. Green, Robert M. Galford
Discovery should optimize three variables:
- Build credibility
- Increase intimacy
- Reduce self-orientation
Credibility
- Bring specific customer and industry knowledge into the meeting. Prepare upfront and avoid questions that you could have researched before the call.
- Ask precise questions that fit the buyer’s world by using customer language—learn and use the terminology they use.
- Speak to senior pain dimensions: revenue, profitability, risk.
Intimacy
- Create psychological safety so the buyer shares constraints, fears, and internal politics.
- Use Crucial Conversations behaviors to explore others’ paths: ask, mirror, paraphrase, and prime.
Reduce self-orientation
- Lower “pitch energy.”
- Keep the conversation centered on them: their context, problems, needs, and how they decide.
- Treat discovery as a fit assessment: understand whether you can help, instead of pushing features.
- Use the Fritzsche idea: keep the ball with the other person. Ask, then pause.
McMahon’s “how champions evaluate trust” provides a practical lens:
- champions evaluate business value, performance value, and experience value. Experience value is where the trust equation becomes visible.
Two-Sided Discovery: Open-Ended Questions, Tell–Explain–Describe, and Insight-Led Prompts
Discovery is not interrogation. Discovery is a two-sided conversation in which you learn and the customer learns.
Use open-ended questions so that buyers can articulate the situation in their own words. A simple structure that keeps you out of interrogation-mode is Tell / Explain / Describe:
- Tell me what happened.
- Explain how this shows up in your day-to-day.
- Describe what “better” would look like.
In addition, use two-sided questions. A two-sided question starts from your point of view—usually a differentiator or a pattern you have seen in the market—and connects it to a risk or problem that the customer might not have named yet. You then ask about it in a way that lets the customer discover and explain it themselves.
Fritzsche’s “Wer hat den Ball?” provides the mindset behind this: you keep the ball with the other person, you ask, and you pause—because people commit more strongly to insights they articulate themselves.
Der Mitarbeiter muss sich selbst klarmachen, wieso er etwas tun soll – meine Aufgabe besteht darin, ihm dabei zu helfen, es herauszufinden.
— Wer hat den Ball?, Thomas Fritzsche
What is true for management could not be more true for sales.
Depth in Discovery: Consequences, Quantified Stakes, and the Cost of Inaction
Time kills deals without urgency because, without a clear cost of inaction, every stakeholder has a rational reason to delay.
When urgency is missing, priorities compete, calendars slip, and “later” turns into quarters. Internal projects lose sponsors, budgets get reallocated, and the buyer gradually normalizes the current pain because the business still runs.
This is why implicated pain matters. If you can connect the problem to measurable impact—revenue leakage, margin pressure, risk exposure, capacity limits—then time stops working against you, because the customer can explain why doing nothing is not neutral.
Depth comes from laddering:
- label → mechanism → constraint → implication → quantified impact.
One learning I refined over the years—shaped strongly by great Business Value Consultants like Andreas Sailer—is to keep asking “So what?” until you reach measurable impact. Percentages help; dollars decide.
Customer Requirements in Customer Language: Criteria That Increase Trust and Clarity
Customer requirements should exist in the customer’s language.
A customer requirement describes what must be true for the customer to reach the Future State and realize the Positive Business Outcomes. It is not your feature list. It is the customer’s set of criteria that any viable option must satisfy.
From a trust perspective, this matters because it increases Credibility and reduces Self-Orientation in the Trust Equation. When you document requirements in their terminology, you show that you understand their world and you signal that the conversation is about their success, not about your product.
McMahon’s “use case, pains, before/after” guidance helps: synthesize in buyer words, then confirm understanding.
Challenger adds a constraint: you must still bring insight. You should not only mirror the buyer; you should help the buyer reframe.
Creating Urgency in Discovery: Why Now, What Changes, and What Breaks if Nothing Happens
Urgency is not a closing technique. Urgency is an outcome of implicated pain.
McMahon’s “Why now?” questions belong in discovery:
- What happens if they do nothing
- What company measurement suffers
- What event makes this unavoidable.
Building a Champion Through Discovery: Tests, Internal Selling, and Stakeholder Access
Champions do not appear because you like each other. Champions form because the pain becomes real and personal.
McMahon’s champion tests set a standard:
- Can they explain why the pain is major
- Can they explain implications of inaction
- Can they tie your solution to business value
- Can they sponsor access, justification work, and procurement/legal paths