I listened to a sales rep run discovery with a qualified prospect. Thirty minutes of questions. The rep was thorough. He asked about their current solution, their team size, their budget, their timeline, their decision process, their technical requirements.
The prospect answered every question politely. The call ended with "let's schedule a demo next week."
We never heard from them again.
I pulled the Gong transcript and looked at what the rep actually asked. Twenty-three questions. Not one of them revealed whether the prospect actually had a problem worth solving or urgency to solve it.
The rep collected information but didn't uncover truth. He qualified the opportunity without understanding if there was actually an opportunity to qualify.
I've made this same mistake hundreds of times. Early in my career, I thought good discovery meant asking lots of questions. I had frameworks—BANT, MEDDIC, SPIN—and I asked every question in the framework.
Then I analyzed our won deals versus lost deals and discovered something that changed how I think about discovery: The questions you ask matter less than what you do with the answers.
What Discovery Actually Does
Most reps treat discovery like a form to fill out. They have a list of questions they need answered—budget, authority, need, timeline—and they ask those questions in sequence.
This approach produces conversations that feel like interrogations. The prospect answers questions but doesn't reveal anything they wouldn't put on a contact form.
The reps who close deals use discovery differently. They're not filling out a form—they're looking for emotional truth.
Form-filling question: "What's your current solution?" Truth-seeking question: "Walk me through the last time your current solution failed you. What happened?"
The first question gets you a product name. The second question reveals frustration, consequences, and urgency.
I learned this by analyzing 200 sales calls—100 that closed and 100 that didn't. I pulled Gong transcripts and looked for patterns.
The calls that closed weren't longer. They didn't ask more questions. But the questions they asked were fundamentally different.
Losing calls asked about facts: "What's your budget? Who makes the decision? What features do you need?"
Winning calls asked about consequences: "What happens if you don't solve this? What's the cost of the status quo? What's driving this now versus six months ago?"
The difference is subtle but critical. Facts tell you if you can sell to them. Consequences tell you if they'll actually buy.
The 15 Questions That Predict Wins
After analyzing those 200 calls, I found 15 questions that appeared significantly more often in won deals than lost deals.
These aren't the only questions reps asked—they're the questions that correlated with wins. When reps asked 10 or more of these 15 questions, their close rate was 34%. When they asked fewer than 6, their close rate was 11%.
Here they are, organized by what they uncover:
Urgency Questions (The Most Important)
1. "What happened that made you start looking for a solution now?"
This reveals the trigger event. Something changed recently—a new executive, a failed project, a competitor move, a regulatory requirement. If there's no trigger event, there's no urgency.
In won deals, 89% of prospects had a clear trigger event they could articulate. In lost deals, only 31% did.
2. "What happens if you don't solve this in the next 90 days?"
This uncovers consequences. If the answer is "nothing critical," you don't have a real opportunity. You have a nice-to-have.
The best prospects say things like: "We'll miss our compliance deadline" or "We'll lose customers to competitors who have this capability" or "Our CEO will replace the team if we don't show progress."
3. "What have you already tried that didn't work?"
This reveals commitment. Prospects who've already invested time and money trying to solve this problem are more likely to buy than prospects who are casually exploring.
One prospect told us: "We tried building it ourselves. Six months and $200K later, it barely works and nobody uses it." That's urgency.
Problem Depth Questions
4. "Walk me through the last time this problem cost you something—a deal, time, money, or reputation."
This makes the problem concrete. Abstract problems don't drive purchases. Specific failures do.
A prospect who says "It's inefficient" is very different from one who says "Last quarter we lost a $500K deal because we couldn't provide the analytics the customer needed."
5. "How much time does your team spend on workarounds for this problem each week?"
This quantifies the pain. If they can't quantify it, they probably haven't felt it enough to justify buying.
The best prospects do math on the call: "We have five people spending about 10 hours each per week on manual work that your product would automate. That's 50 hours a week, 200 hours a month..."
6. "Who else in your organization is affected by this problem?"
This reveals scope. If the problem only affects one person, it's hard to justify budget. If it affects three departments, you have a bigger opportunity.
Decision Process Questions
7. "Who has tried to solve this before and what happened?"
This uncovers political landmines. If the last person who tried to fix this got fired or moved to a different role, your prospect is taking a career risk by buying from you.
8. "What does success look like in 6 months if you solve this?"
This creates a vision. Prospects who can articulate specific success metrics are more likely to buy and more likely to get internal approval.
Bad answer: "Things would be better." Good answer: "We'd reduce time-to-close by 30%, which would let us handle 50% more deals with the same team size."
9. "What would prevent this from getting approved even if you love it?"
This surfaces objections early. Some reps avoid this question because they're afraid of creating objections. But objections don't disappear if you ignore them—they just kill the deal later.
The best prospects say things like: "We'd need to show ROI within 6 months" or "We'd need buy-in from IT on security" or "We'd need to fit within our existing budget cycle."
Now you know what to address.
Budget Reality Questions
10. "Have you already allocated budget for this, or would you need to find budget?"
This cuts through the vagueness of "What's your budget?"
Prospects who have allocated budget close faster. Prospects who need to "find budget" often don't close at all.
11. "What did you spend on trying to solve this problem last year?"
This anchors their investment. If they spent $100K on a failed solution last year, your $75K solution feels reasonable. If they spent $0, you're creating a new budget line—much harder.
Competitor Questions
12. "Who else are you looking at and why?"
Obvious question, but most reps ask it wrong. They ask "Are you looking at competitors?" which gets a yes/no answer.
"Who else are you looking at and why?" gets you positioning intelligence. You learn what the prospect values and how competitors are positioning against you.
13. "If you could only pick one capability that the winning solution must have, what would it be?"
This reveals their primary decision criterion. Everything else is secondary.
When you know the one thing that matters most, you can position around it or disqualify early if you don't have it.
Commitment Questions
14. "If we can show you this solves your problem and the pricing works, what would prevent you from moving forward?"
This is the trial close. It surfaces hidden objections and tests commitment.
Prospects who say "Nothing, we're ready to move" close fast. Prospects who say "Well, we need to see what else is out there first" are still shopping.
15. "What's your ideal timeline for having this up and running?"
This differs from "When do you want to buy?" It focuses on implementation, which reveals how seriously they're thinking about this.
Prospects who say "We need to be live by end of Q2" are serious. Prospects who say "No particular timeline" are tire-kickers.
How to Actually Use These Questions
Here's the mistake I see reps make: they treat this like a checklist. They ask all 15 questions in sequence and wonder why the prospect feels interrogated.
These questions work when you weave them into a conversation, not when you fire them off like a survey.
The best discovery calls I've listened to ask 8-12 of these questions over 30-45 minutes. They follow the prospect's answers, not a script.
Here's what that looks like in practice:
Rep: "What made you start looking for a solution now?"
Prospect: "Our new VP of Sales wants better visibility into pipeline."
Rep: "Interesting—walk me through the last time the lack of visibility cost you something. What happened?"
Prospect: "Last quarter we thought we were going to hit our number based on what reps were reporting. We missed by 30%. The CEO was blindsided."
Rep: "That's painful. What happens if you don't solve this in the next 90 days?"
Prospect: "The VP has basically said if we don't have better forecasting by end of quarter, heads will roll."
Notice how each question builds on the previous answer. We went from "VP wants visibility" to "we missed our number" to "people will get fired" in three questions.
That's not interrogation—that's uncovering truth.
The Questions Most Reps Ask That Don't Matter
I also found questions that appeared frequently in calls but didn't correlate with wins. Reps ask them because they're in the frameworks, but they don't actually help close deals.
"What's your role?" You should already know this from research.
"How many people are on your team?" Only matters if team size affects pricing or implementation.
"What features are most important to you?" This gets you a wishlist, not buying criteria.
"When do you want to buy?" Nobody says "I want to buy next week." Ask about implementation timeline instead.
"What's your budget?" Prospects lie or don't know. Ask what they spent on the problem last year instead.
Every minute you spend on questions that don't predict wins is a minute you didn't spend uncovering urgency or consequences.
What Good Discovery Feels Like
The best discovery calls I've listened to don't feel like sales calls. They feel like strategic conversations.
The rep asks a question. The prospect thinks before answering. The rep follows up based on what they heard. The conversation goes deep on one topic before moving to the next.
There's silence. There's thinking. There's storytelling.
Bad discovery sounds like: "What's your budget? Who makes the decision? What features do you need? When do you want to buy?"
Good discovery sounds like: "Walk me through what happened... And when that happened, what did you try? ... And what prevented that from working? ... So if you don't solve this, what's the consequence?"
The difference is depth. Bad discovery covers many topics shallowly. Good discovery covers fewer topics deeply.
The Brutal Truth About Discovery
Most reps skip discovery or rush through it because they want to show the product. They think the demo is what sells.
But the demo only works if discovery created urgency first. If the prospect doesn't believe they have a problem worth solving, the best demo in the world won't close the deal.
I've watched reps deliver perfect demos to prospects who weren't ready to buy. The prospect says "looks great" and disappears.
I've also watched mediocre demos close deals because discovery was excellent. The prospect was so convinced they needed to solve the problem that the demo just needed to prove the product worked—it didn't need to be perfect.
Discovery is where deals are won or lost. The demo is just confirmation.
Yet most reps spend 80% of their time perfecting their demo and 20% on discovery. That ratio should be reversed.
How to Know If Your Discovery Was Good
You can't judge discovery quality during the call. You judge it after.
Good discovery produces three outcomes:
The prospect agrees to next steps without hesitation. They're not "thinking about it"—they're scheduling the next meeting before the call ends.
You can articulate their problem better than they can. After discovery, you should be able to write a 3-paragraph summary of their problem that they'd read and say "yes, exactly."
You know what would kill the deal. You know their constraints, their politics, their budget reality. You know what could go wrong.
If discovery ended and you can't articulate their specific problem, their urgency, and their constraints, you didn't do discovery—you had a conversation.
The Mistake I Made for Years
Early in my career, I thought discovery was about qualifying opportunities. I asked questions to determine if this was worth my time.
That's backwards. Discovery isn't about qualifying them—it's about creating urgency.
The best reps use discovery to make prospects realize they have a bigger problem than they thought. They ask questions that surface consequences the prospect hadn't fully considered.
One rep I coached did this masterfully. A prospect called saying they wanted better reporting. That's not urgent—it's a nice-to-have.
The rep asked: "Walk me through your last board meeting. What questions did the board ask that you couldn't answer?"
The prospect paused. "They asked about customer retention by segment. We couldn't answer it. It was embarrassing."
Rep: "What happened after that?"
Prospect: "The CEO pulled me aside and said if I don't have better data by the next board meeting, we need to talk about my role."
Rep: "When's the next board meeting?"
Prospect: "Six weeks."
That's urgency. The rep didn't create it—he uncovered it with the right questions.
Start With Three Questions
If you've never done deep discovery before, don't try to ask all 15 questions perfectly. Start with three:
"What happened that made you start looking now?" (Trigger event)
"Walk me through the last time this problem cost you something." (Consequences)
"What happens if you don't solve this in 90 days?" (Urgency)
Master those three questions. Get comfortable with silence while prospects think. Practice following up based on their answers instead of moving to your next scripted question.
Those three questions will tell you if you have a real opportunity or a tire-kicker.
Everything else is refinement.
The difference between reps who hit quota and reps who don't isn't product knowledge or demo skills. It's the ability to uncover truth in discovery.
Learn to ask questions that reveal urgency and consequences. Everything else follows from that.