--- title: My prospect listed a bunch of pain points on the discovery call. How do I find the one that actually matters? description: Prospect listed a bunch of pain points on your discovery call? Sales trainer Josh Hedaya shows how to find the one that hurts and is worth solving first. --- [Skip to content](https://go.connectionselling.io/connection-selling-blog/my-prospect-listed-a-bunch-of-pain-points-on-the-discovery-call.-how-do-i-find-the-one-that-actually-matters#main-content) Get started Get started # My prospect listed a bunch of pain points on the discovery call. How do I find the one that actually matters? ![Josh Hedaya](https://7528315.fs1.hubspotusercontent-na1.net/hub/7528315/hubfs/raw_assets/public/mV0_d-cms-elevate-theme_hubspot/elevate/images/avatar-placeholder.jpg?width=48&height=48&name=avatar-placeholder.jpg) Josh Hedaya October 22, 2026 **TL;DR:** The pain worth solving first is the one the buyer feels, so ask what each problem does to them before you solve anything. Sales trainer Josh Hedaya of Connection Selling teaches sellers to take the problems one at a time, ask what each one means, ask how it affects the buyer, then ask what happens if nothing changes. The problem they answer with feeling is the one to lead with. In a one-on-one training, Josh played the owner of a small treatment center so a rep at a billing company could practice. He gave the rep everything at once: the insurance was beating him up, every patient seemed to have a different insurer, there was compliance paperwork he never knew existed, he was managing patients, nurses and staff, people weren't paying on time, and he was "bleeding dry here, man." The rep heard all of it and jumped to a fix: it sounded like the owner needed some help with compliance, which his company offered. When Josh stopped the role play, the rep explained why: "you were giving me so much information of all these pain points that I couldn't keep track of like which pain points, so I was like just trying to fix out the solution." The buyer has opened up and named five problems. Which one do you go after? (If your buyers won't open up in the first place, start with [I ask all the discovery questions I've been taught, but prospects still don't tell me the truth. What should I do?](https://go.connectionselling.io/connection-selling-blog/discovery-questions-prospects-dont-tell-the-truth)) ## Why does a prospect list so many problems on a discovery call? Because once you really listen, buyers tell you a lot, and most of what comes out first is the logical layer. Josh warned the same rep about this earlier in that session: "when you really begin to listen the way that you did yesterday, people start giving you so much information that you have to, like, begin to weed, like, what's important versus what's not, and they're also gonna start contradicting themselves, too." The first list is usually logical: the data isn't integrated, the forecasts are missing. In a course module, Josh names the trap that comes with it. The seller gets excited about all the logical things his product does and starts talking. "Do not fall into that trap. Not yet." Underneath every logical problem is a feeling. Josh's version for the missed forecasts: "I'm burning the midnight oil," the CFO is "getting down my neck," and "how much time am I wasting?" ## How do I find the pain point that actually matters? Take the problems one at a time. Ask what they mean, then ask how it affects them. The one they answer with feeling is the one that matters. In a group training, a consultant described a big financial client's problem to Josh in full technical detail: one platform running the whole business, not working, a second instance needed and a migration to plan. Josh stopped him there. "So talk to me like I'm five. What's the real problem?" "The toy they're playing with doesn't work for everybody." "How does that affect them?" "It's causing a lot more time, effort, double-checking work." Two questions took a paragraph of jargon down to people double-checking their work. That is the problem a buyer feels. The questions Josh uses to get there are plain: - "How do you mean by \[their word\]? 'Cause that sometimes means different things to different people." - "When it goes up and down like that... what does that do to you?" - "How does that affect them?" (when the buyer is talking about a team) - "What type of position did that put you in?" A course example shows how far a few of those questions go. A VP of clinical operations starts with logic: patient data isn't syncing between systems, and nurses spend half their shifts on manual data entry. Three questions later the buyer is saying their reputation was on the line and "it's my name on it." The sync problem was the list. The name on it was the pain. It is worth slowing down for. In a group training, Josh put it this way: "You take leaps in the cycle when you get the emotion, 'cause they just, they trust you. There's a connection." ## How do I know which pain is urgent enough to solve first? Ask what happens if nothing changes. A problem the buyer is willing to live with is not the one to lead with. Josh calls these what if questions. After the buyer has laid out the problems, he asks, conversationally, something like: "you've outlined all of these challenges... I'm just curious, what if you stay status quo?" He is clear they are not pressure questions. What they do, in his words, is give you "an inclination into just how much they actually need to change right now." Some buyers answer right away that they need to fix it. Some shrug and say they could keep going a while longer. Josh's course gives the reply for that one, said with curiosity: "Oh, really... you're really willing to settle for that?" Josh teaches that a buyer can have a need and no real desire to change it. The what if question tells you which problems they actually want to change. Then ask one more question, the one Josh uses once the main problem is on the table: is there anything else you would change right now? In the role play below, the answer was "No, that's about it, man. Cashflow." That is what it sounds like when you have found it. ## Should I ask the prospect to rank their problems? Let the buyer choose where to start, but only at the end of discovery, after they have told you how each problem affects them. Josh closes discovery with a transition statement. It plays back a problem the buyer named and the feeling that came with it, in their words ("you know how you said that... and because of that..."), says what might possibly help, and ends with a question: "where would you like us to start?" In Josh's words, "it's always an option to them." By then the buyer has already told you which problem is costing them and which one they can live with. ## How do I steer the discovery call back to the problem that matters? Go back to why they took the meeting. Every time the call drifts into requirements, pricing or dates, return to what is not working for them. In one training, Josh put it this way: "even if they go down the yellow brick road of requirements and pricing and close dates, you, you still go back," because "you need to know why are they here really. Like, what's not working that they wanna meet with a salesperson?" The buyer has to say it out loud, and Josh explains why: "they persuade themselves, 'Oh, I have a real problem and this person really listens to me.'" In B2B sales with several meetings, do it again at the top of every call. Josh told the rep from the opening story: "every call you have, you have to retie them back for the first two to five minutes of, like, what are your real problems at?" ## What does this sound like on a real call? An example from a one-on-one training It sounds slow, and it narrows. Here is how the role play ended. After the compliance jump, Josh told the rep he never wanted him to get to solutions in their role play until he had taught him solutions. Then they switched seats. The rep played a treatment center owner who had called in from the website. Josh played the seller. (The business and its numbers were made up for practice. The questions are the real thing.) The owner said he was "looking for some assistance." Josh asked, "How do you mean by assistance?" The owner said he felt in over his head. Josh didn't chase it yet: "I wanna understand what you mean by over your head in a second, but do you mind if I ask you a couple more questions before I tell you what we actually do?" Josh asked how long he had owned the place and what was going well. Great staff, the owner said, good results with patients. "But, um, I just don't know how to get a consistent cashflow." Josh: "Okay, how do you mean by consistent cashflow? 'Cause that sometimes means different things to different people." Some months covered the cost of his employees, some months brought in far more. "It's, like, up and down, up and down, up and down. And, uh, I really don't have a good billing team." Josh: "When it goes up and down like that... what does that do to you?" "Gives me so much anxiety." Josh asked whether it affected his day to day. The owner said it made him "go kick the cat" at the end of the day. Then Josh asked the narrowing question: "other than the cashflow going up and down, what, is there anything else you would change right now?" "No, that's about it, man. Cashflow." A few minutes earlier, the same rep had heard a pile of problems and picked compliance. This time the buyer picked cash flow himself, and said what it was doing to him. Josh stepped out of the role play and asked, "Did you see what I just did here?" At the end of the session, the rep summed up what he needed to work on: "I need to ask more clarifying pain questions just to pinpoint the actual pain behind the pain." This was a training, so there is no deal outcome to report. ## Checklist: before you pick the pain to solve first - Note every problem the buyer names, in their words, and fix none of them yet. - Ask what they mean by each one, even the ones you think you understand. - Ask what it does to them, or to their team, when it happens. - Ask what happens if nothing changes, and listen for whether they'd settle for it. - Ask if there's anything else they would change right now. - Play back the problem they answered with feeling, then ask where they'd like to start. - Open the next call by asking what their real problems are today. ## FAQ ### What's the difference between a logical pain point and an emotional one? The logical pain point is the fact: missed forecasts, cash flow that goes up and down, a platform that doesn't work for everybody. The emotional one is what that fact does to the buyer: the late nights, the CFO on their neck, their name on a project that is failing. In a group training Josh put it simply: "people make decisions based on emotion." So the second one is the one to find. ### When should I start talking about my solution? After the buyer has told you the problems, how they affect them, what happens if nothing changes, and how they would want it solved. Josh's advice to a rep who jumped to a fix too early was simple: "Slow down. Key is always go slow." ### How many pain points should I present back to the buyer? Only the ones the buyer told you matter, and usually that is two or three. Josh's experience is that "you're always kinda solving the same two to three problems for people." For how to present back only what they said, see [What should I say when a prospect asks what makes us different from our competitors?](https://go.connectionselling.io/connection-selling-blog/what-makes-you-different-from-competitors) ### What if the buyer contradicts themselves? Expect it. Josh warns that buyers will say they don't really have a problem and then, a few sentences later, tell you what it is. His advice is to "take it all in and really just be with them," then ask about what they just said. Want more of how Josh teaches discovery? His free guide, [Secrets of B2B Follow-Up](https://go.connectionselling.io/follow-up), shows how to use what buyers tell you to keep the deal moving. ## Share this post [mailto:https%3A%2F%2Fgo.connectionselling.io%2Fconnection-selling-blog%2Fmy-prospect-listed-a-bunch-of-pain-points-on-the-discovery-call.-how-do-i-find-the-one-that-actually-matters](mailto:https%3A%2F%2Fgo.connectionselling.io%2Fconnection-selling-blog%2Fmy-prospect-listed-a-bunch-of-pain-points-on-the-discovery-call.-how-do-i-find-the-one-that-actually-matters) ## Keep reading ### [What should I say when a prospect asks what makes us different from our competitors?](https://go.connectionselling.io/connection-selling-blog/what-makes-you-different-from-competitors) ### [![They said yes, then went quiet. Josh Hedaya, Connection Selling](https://go.connectionselling.io/hs-fs/hubfs/blog-images/prospect-agreed-to-meeting-then-stopped-responding.png?width=1200&height=627&name=prospect-agreed-to-meeting-then-stopped-responding.png) A prospect agreed to take a meeting and then stopped responding. How do I get them to reply?](https://go.connectionselling.io/connection-selling-blog/prospect-agreed-to-meeting-then-stopped-responding) # Connection Selling --- Privacy Policy · Legal · © 2026. All rights reserved. ```json { "@context" : "https://schema.org", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Josh Hedaya", "url" : "https://go.connectionselling.io/connection-selling-blog/author/josh-hedaya" }, "dateModified" : "2026-10-22T13:16:25.689Z", "datePublished" : "2026-10-22T13:16:25.000Z", "headline" : "My prospect listed a bunch of pain points on the discovery call. 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