Stop adding more problem questions. Sales trainer Josh Hedaya of Connection Selling teaches that buyers hold back when they feel sold to. His fix starts somewhere sellers don't expect: ask what is going well first, then what could be better, then ask what they meant by the words they just used. The first answer is rarely the whole truth.
Below are the exact questions Josh teaches and what to say when a buyer insists everything is fine.
You learned the discovery questions. You asked about their challenges and what keeps them up at night. You got polite, surface-level answers and a deal that went nowhere.
Josh hears this constantly from the sellers he trains. One put it this way: "I'm still having trouble getting to those emotional pain points." Another, in a group training, asked what to do when a new prospect has pain points but "they just won't open up."
Here is how Josh explains it:
Josh also teaches what he calls two truths. The first thing a buyer tells you is rarely the real reason they agreed to talk. There is almost always a second truth underneath. In one coaching session, Josh summed up a role-play buyer's answer in five words: "Well, it's going great, but." Everything after the "but" is the second truth.
Josh's method rests on being detached from the sale. You are there to find out whether the buyer even has a problem they want to solve. If they don't, no problem. On a live webinar, Josh told one seller that memorized wording misses the point: "What matters is what you said, it's the intent, the honesty." When a buyer asks why you are asking, give the honest reason, the way Josh does: "the reason I'm asking is I don't know that first I can help you."
Before you ask anything about problems, ask what they like. These are from Josh's course:
Josh says this question "is gonna pretzel brain them." Buyers do not expect a seller to ask what the competition does well, so they relax. It also tells you what they want to keep, which belongs in your presentation later. Ask a second one before moving on: "Anything else that's going well?"
Once they have talked about what works, Josh moves to the dislike, in a curious, almost throwaway tone:
If the answer is lukewarm, something like "well, it's okay," Josh's course says to lean in playfully: "Well, hold on, you don't sound so sure about that. What is it exactly you dislike?"
This is where most of the truth gets lost: the buyer says something with feeling, and the seller moves to the next question. Josh teaches three things to listen for: adjectives like frustrated, exhausted or challenging; phrases with emotion in them; and words that are unique to that buyer. When you hear one, ask about it:
This is how you reach the emotional pain. Josh compares a buyer's problem to an iceberg. The logical problem sits above the water. The bigger part, how it is actually affecting them, sits below. The way down is a plain question about the word they just used. And let them answer it. In a group training, Josh corrected a seller who suggested the answer inside the question: if "you ask a question and then lead them with what you think it might be, you limit the opportunity for them to speak."
When a buyer names a problem, don't jump to your solution. Josh asks a question that sounds backwards: "Have you gone to your existing vendor to see if they can even fix these problems?" Or, "Have you looked internally?" He told a webinar audience it makes the buyer see you as a trusted advisor, detached from the sale, and it tells you how committed they are to changing.
Some buyers will tell you they have no dislikes at all. For them, Josh uses what he calls the unlock the vault question. Asked with complete detachment, it sounds like this:
"Well, I'm just curious then. If it sounds like things are going well for you, which is great, what made you want to pick up the phone and even have a conversation with a salesperson? Usually, salespeople are the last people you want to engage with."
In a group training, Josh told sellers that about 10 to 15% of the time they get a meeting, the buyer doesn't actually have a problem. The vault question gets you to that truth fast, either way.
One sales director Josh coaches heard a buyer mention "challenges" early in a call. She wanted to ask what kind. She didn't, and she told Josh why: "I didn't want to deviate from the script."
Josh's read was that she was getting overwhelmed by the script. In a later session, looking at her long question list, he told her to throw most of it out and start with about five. His course describes the same arc: learn the questions until they are in your body, then "you kind of get to throw it out" and follow the buyer.
On one of Josh's live webinars, a seller of industrial computers to equipment manufacturers took the hot seat. Big-ticket deals, a 12 to 18 month sales cycle. He had presented his proposal in person, twice. Now it had been sitting for months with one decision-maker who kept saying he was "talking to people internally." The seller's frustration was plain: "you guys made it sound urgent like you need a product, and now it's like it's been sitting for months. Like, do you really need this?"
Josh's diagnosis: "you're not getting to the truth." Then he asked one question. What did the buyer like about his current system? The seller hadn't asked. "It was more about what they needed and then filling that gap."
The seller admitted that asking about the current vendor made him uneasy: "I almost feel like I'm asking them to violate, like, their NDA." Josh gave him the line for that: "Oh, I get it. I don't need to know the company. What I'm more actually interested in is what do they do well? How is it helping you?" He also pointed out the seller had never asked what it would look like for the buyer once the problem was solved.
The buyer had just invited him to stop by the office the next week. Josh's advice was to start that visit by owning the gap: "I didn't even ask you this question and it's kind of important. Can you tell me what you like about your current" system? "And watch him get disarmed."
One more worry: about half the time, the seller said, buyers ask why he wants to know what they like when he came to show them something. Josh's answer was step 1. Give the true reason. The recording does not show how the deal ended.
Usually because they still see you as a salesperson about to pitch them. Josh starts with what is going well, stays detached from the sale, and asks about the buyer's own words. Once buyers feel you are curious, they start telling you what is really going on.
Listen for adjectives and emotional phrases, then ask what they meant. "You said exhausted. What do you mean by that?" "Has that had an impact on you?" Josh teaches that the logical problem is the tip of the iceberg, and the buyer's own words are the way below the surface.
Believe them, and ask what they like about the vendor. Then ask whether anything could be improved. If they still have nothing, ask the unlock the vault question: if things are going well, what made you want to have a conversation with a salesperson? Their answer is usually the real reason for the meeting.
Tell them the truth. Josh's version: the reason you are asking is that you don't know yet whether you can help, so you need to know what is working and what they care about. He teaches that the intent behind the words matters more than the words themselves.
Ask fewer of them and follow the answers. Josh warns that questions asked like a punch list sound like an interrogation. Ask one question, then ask about what they said, using their words, before you go anywhere else.
Want more of how Josh teaches discovery? His free guide, Secrets of B2B Follow-Up, shows how to use what buyers tell you to keep the deal moving.