5 Pain Questions That Close Deals


Notes
Have you ever had a prospect who seemed truly engaged and excited about your product or service? They asked all the right questions, and gave you every indication that they were ready to buy? But then, go completely silent? Well, you’re not alone.
In this episode of The Slow Pitch Podcast, host Rob walks through a real client scenario where everything looked like a done deal… until it wasn’t. What happened next is a sales problem nearly every business owner, salesperson, or consultant has experienced: the ghosting prospect and the lack of pain.
Common Sales Problems: Why the Deal Falls Apart
One of the most frustrating sales problems is the disappearing act. In Rob’s story, a golf instructor named Ken meets an enthusiastic prospect who wanted help with his swing in time for a member-guest tournament. Ken gave away too much value upfront, offered a free mini-lesson, and failed to secure a follow-up agreement. Sound familiar? What appeared to be a solid lead unraveled quickly because the pain behind the purchase wasn’t explored in enough depth.
Prospect Engagement Is Not the Same as Buying Intent
At first, the potential client seemed highly engaged because he asked questions, thanked Ken, and expressed excitement about improving his game. He was excited. But the thing to know is that prospect engagement does not guarantee a sale.
In this episode Rob breaks down the mistake many sellers make: confusing surface-level engagement with true intent. This also relates the need to dig a little deeper. Just because someone listens, nods, or smiles doesn’t mean they’re ready to buy. They may not have a pressing problem (real pain) or they may not feel it’s urgent enough to pay for a solution.
Uncover the Pain: A Sales MUST
Pain is the real driver of action. In Ken’s case, the prospect mentioned an upcoming tournament but Ken failed to ask the critical question: “What happens if you don’t improve your swing by then?” He might have found out that it was a red herring and really wasn’t an issue. If Ken had asked the right questions to find out, he could have immediately moved on to the next actual prospect with pain.
Rob emphasizes the importance of exploring the pain behind the problem. Was the buyer embarrassed by his performance? Was he trying to impress someone important? Without understanding those emotional and practical consequences, Ken couldn’t position his offer as a must-have solution.
When pain is vague or unclear, there likely won’t be a sale.
Better Sales Starts with Better Questions
One key takeaway from this episode is that sales isn’t just about presenting solutions—it’s about asking strategic questions.
As Rob puts it, “No pain? No sale.” And the way you uncover pain is by asking thoughtful, probing questions such as:
-
What happens if you don’t fix this before your deadline?
-
Why are you trying to solve this now?
-
What’s the impact of doing nothing?
In this real-world scenario, had Ken asked these types of questions, the outcome might have been very different. This is where effective sales coaching can transform your results. Building a habit of curiosity, active listening, and diagnosing rather than pitching will transform your sales career.
The DiSC Profile: Understand Buying Behavior Faster
Another missed opportunity in Ken’s conversation was understanding the DiSC profile of the buyer. Rob discusses how different personality types buy in different ways—and if you don’t recognize who you’re speaking with, you risk communicating ineffectively.
For example:
-
A High “I” may show excitement but not follow through.
-
A High “S” might delay decisions until consulting others.
-
A High “D” will want direct results, quickly.
-
A High “C” will need all the data before moving forward.
By observing and evaluating a prospect’s behavior, tone, and decision-making style, you can tailor your approach and avoid wasting time. Ken assumed the buyer was an “I,” but never confirmed it. A mistake that may have cost him the sale.
The Danger of Giving Away Too Much for Free
Another common mistake that Ken made was giving away free services. While offering a taste of your service can sometimes help build trust, it often won’t close the sale. In fact, it may just solve enough of the prospect’s pain to remove their urgency to buy. Rob explains how free consultations, trials, or “quick fixes” can often backfire if not positioned strategically. The lesson? Make your value clear, but don’t do the work before you’re hired.
Sales Coaching Tip: Don’t Chase, Diagnose
Rob closes the episode with a powerful mindset shift for anyone in sales: “You don’t need more leads. You need better conversations.” That means qualifying earlier, digging deeper, spending more time diagnosing instead of selling, and letting go when a prospect clearly isn’t ready or willing to move forward.
If you’ve been ghosted by a prospect, you’re not alone. You can reduce how often it happens to you by focusing on:
-
Solving sales problems at the root
-
Asking stronger pain-based questions
-
Reading and reacting to DiSC profile cues
-
Driving real prospect engagement
-
Applying proven sales coaching principles
…you’ll close more deals and waste less time chasing lukewarm leads.
Remember: Better questions lead to better outcomes.
Slow down, ask better, and close more.
📬 Let’s Talk Sales
If you’ve run into a similar challenge and want to improve your process, Rob offers 1:1 coaching and team sessions.
📧 Email: Questions@TheSlowPitch.com
📞 Call/Text: (608) 708-SLOW
⏱️ Timestamps
00:00 Intro
00:45 The Sales Problem: Excited Prospect Disappears
02:30 Surface Engagement vs. Real Pain
04:15 Critical Questions Ken Missed
06:00 Why Pain Matters More Than Interest
07:20 Giving Too Much Away Too Soon
09:00 Reading the DiSC Profile
10:40 Coaching Advice to Avoid Future Ghosting
11:45 Final Sales Coaching Tips
Keywords: Sales Problems, Prospect Engagement, Pain, DiSC Profile, Sales Coaching
Related Episodes:
Sales Pain Questions: How to Create (For an Emerging Market)
How to Find Pain in Sales. What Is Pain in Sales?
Sales Slump – The Pep Talk You Need Now!
Podcast Recorded on Squadcast.fm
NOTE: Some links may be affiliate links, which means we get paid a commission when you purchase, but it the cost remains the same for you.
Music: "Clydesdale Funk" by Cast of Characters, written by: Dustin Ransom.
The Episode
Rob 00:00
Have you ever had a prospect who seems super excited to work with you? They answered some of your questions. They agreed with what you were saying. They said things like, hey, this is this is really good. I really appreciate your help with that. But then they stopped replying to you, well, this can happen more than you like, but some of you might be experiencing some of it more now than maybe ever before. I mean, it’s summertime.
Rob 00:27
Things get slow, vacations, travel, school’s out, all that kind of stuff, right? Well, I had a client call me recently about this, and I think it might be tied into some of the things that I’m gonna share with you today. So let’s, let’s dig into that.
V/O 00:41
This is The Slow Pitch Podcast.
Rob 00:43
Welcome everybody to The Slow Pitch and we usually talk about sales problems, things that come up, things that happen when you’re in sales, things that might be causing you issues. And hopefully people at any level can listen to this episode and any episode that we cover to help them improve in their sales process. So, let’s talk a little bit about this client that I was working with who said to me basically.
Rob 01:08
So let me give you a little background. First, I guess he’s a golf instructor. He’s got multiple clients. He teaches them how to play golf better, and that’s kind of cool. So, his name is Ken. Ken is a really nice guy, almost to the point where he does things he probably shouldn’t do for people, and then people like it about him, and I like that too, but it’s probably causing him some issues.
Rob 01:28
And so I wanted to talk about this because it kind of relates to a lot of different sales situations, while things slow down for him sometimes. And yes, summertime is the time that he should be gearing up, and he feels like he should be getting more clients right now, or he should have sold more clients, and now he’s kind of freaking out because he’s like, I haven’t gotten enough clients to make my clients to make my summer worth my efforts here. What do I do? And he’s a little bit scared, and I get that.
Rob 01:47
So he was telling me about the situation where he had somebody come to him who wanted to help him fix his slice and even work on some of their short game. And, you know, Ken took a look at the swing, did some, you know, checking some things to see if he could work with it. And this client, or this potential client that Ken was working with, was pretty much engaged with Ken in a conversation, like everything was good. Like the guy asked questions.
Rob 02:09
They went back and forth on questions. It was kind of like he was in a session, almost. And I think Ken was trying to show him what he could do. Ken said, alright, let me put together a package for you that will help you work on the slicing issue you’ve got going on, and the swing mechanics, some of the short game things. Let’s put together a plan and let me get that. Put that together for you.
Rob 02:31
The guy was really happy with that. He wanted that information. He wanted to know how much it was going to cost. Ken didn’t talk about the money at all. He was just going to talk about it later. And I don’t know why, but that’s what he decided to do. A little more background here. Ken had met with this potential client at a networking event, and they kind of hit it off a little bit.
Rob 02:50
They were working on playing around with this idea of improving something for a member guest tournament that was coming up. And the guy that was talking to the potential client, really was kind of complaining a little bit about how he was trying to be better at golf. He was explaining how he was very inconsistent on the course. He couldn’t hit Short Shots all the time.
Rob 03:10
He really wanted to improve. And so that’s kind of how they started their conversation. Ken told them, hey, stop by. I’ll see if I can help you out. And so that was kind of nice. They, you know, worked on a few things, and they did it, essentially, Ken did it for free. It was just a little bit of time, but Ken thought it was okay.
And when they talked about, kind of, one of the things that the lesson package might include, without getting into the some of the numbers, Kenny kind of showed him a couple things right on the spot, like he just kind of told him, here’s how you should be standing a little bit differently.
Rob 03:27
Here’s where you should be positioning the ball a little differently. All that’s great, right? Ken said, Nick, I kind of made a comment, hey, that already feels better. I really am excited to help get this thing going and make my game just so much better. And that was music to Ken’s ears.
Rob 03:49
Right after that little session, Ken went to reach out to this guy and wanted to talk about this six-week program that he was putting together. Had some feedback about the swing analysis and about his plans on how to get him on track, to start to work on that short game, start to get things in order and make his whole game get better.
Rob 04:06
But guess what happened when Ken raced out, that guy just didn’t answer. He did not respond. He didn’t say, hey, that sounds great or no, thanks. It just was nothing, no response. So, we waited a little bit longer. He said, hey, I don’t know what happened here. Are you still interested in that kind of thing? He did that a few times, and the guy just never responded back.
Rob 04:22
So he called me and he said, hey, I don’t know what happened here. Do I continue to follow up with this guy? What do I do? Do I let it go? Is this guy never coming back? What happens? What do I do? And it dawned on me that it’s highly likely that a lot of other people have gone through something like this, whether that’s in a golf scenario or somebody else’s scenario.
Rob 04:40
So, let’s talk a little bit about what went wrong in this whole situation. To me, here’s a couple things to keep in mind. I think the interest was actually there. That guy really wanted to get a golf lesson. What didn’t happen was Ken asking all the right questions. I mean, to me, the initial question is, is, okay, was it real? Was the interest really there? How do we know?
Rob 05:00
Maybe the interest was there, but, was the pain there too, because maybe the pain wasn’t really there. And by that, I may just mean this guy says he wanted to work on this, but how badly did he really want to work on it and improve it?
Rob 05:12
And I think Ken could have asked some extra questions, and I’m going to give you these questions because they kind of correspond a little bit with a lot of business people that are out there, or sales people are out there, they can use these same types of questions sometimes on a situation is very similar, but just not in the same world of golf, let’s say right.
Rob 05:29
So think about it this way. What Ken should have maybe asked was, what happens if you don’t fix this problem before your member guest tournament? Because remember, he mentioned a tournament coming up, and he was frustrated. He let that go. Ken just let that go right on by. It went right over his head. Didn’t even see it, hear it.
Rob 05:45
When Ken was telling me the story, I asked him, well, why was he getting instructions? Why was he doing this? And that’s when that came out. He didn’t even think about it when he told me the story. So that’s the first thing is, what would happen if you didn’t get this fixed before the tournament? Maybe, the guy didn’t care. Maybe there was no reason to even fix it.
Rob 06:04
Maybe the guy’s like, I just didn’t want to be embarrassed. You know, maybe there’s this one little tweak that Ken did, that was all he wanted to fix. Well, we all know if you’re golfing, that’s probably going to come right back after a little bit, if you haven’t practiced enough.
Rob 06:12
The other question that Ken could just ask easily is, hey, would you still just keep enjoying golf, regardless if you fix it? I mean, maybe, maybe it’s not that important to fix this problem. Maybe fix this problem. Maybe instead of slicing to the right or to the left or whichever way he was going, why don’t you just aim a little the opposite way and let it go into the set like, what’s the problem with just doing that right now as an instructor?
Rob 06:33
That’s probably not sounding like a very good question, but what’s coming down to is, for anybody in business or anybody in sales, by asking that question, you’re making that person who’s trying to buy your services, let’s say, explain why they need that service, like, what happens if you don’t fix it? It’s a simple question, and especially with this guy who had the member guest tournament coming up.
Rob 06:53
The second thing I think Ken really did wrong was he gave away way too much information. I mean, he gave him a kind of a free swing lesson, and that’s nice. If you’re a big company, you have multiple people walking in the space all the time, and you really don’t have to worry about selling to every single person, right? You don’t have to have all that worry, but, but Ken’s just a single guy working on his own thing. He’s got a certain number of people that he can fit into his day. He needs to have a certain number, right in order to make sure he feels comfortable.
Rob 07:19
By giving that free lesson. He’s basically taking away and giving them some relief to their pain. This guy got a small little tweak. The guy was happy about that. That guy walked away going, I learned something. I took something away with it. And you know what he might do is, like, six months from now, might come back to Ken and say, hey, can you just take a look at something real quick and then just do another whole little round of that and disappear again? Right?
Rob 07:40
So don’t do the free thing. I don’t understand why. Almost any situation where somebody would give away something for free, when you are the expert, if you’re the expert, it’s worth you getting paid. And if you do that by giving away something free, you’re basically solving their problem before you even have an agreement. Now, if it’s a small little thing and you want to just let this person improve and walk away, that’s okay.
Rob 08:00
Listen, that’s your choice. But if you need the sale, or you want to have a sale, or you want to have this client, you can’t do it that way. You have to make them go through the sales process of understanding why the pain is there, making the decision of whether or not they want to fix that problem and how much it’s going to cost them by not doing that.
Rob 08:18
Like, what if Ken had asked that guy, if you don’t fix it by the member guest tournament, what happens? And the guy came back and said, Oh my goodness. One of the people that I’m going to be playing with is a critical client that I just don’t want to look stupid in front of. It’s going to be embarrassing if I don’t do this right and play in front of this guy, right?
I mean, I have got three months to fix this. I just don’t want to be shaking something off into the woods right off the tee box, right? So that might have been enough fear that Ken could have just said, okay, we can fix that. It’s okay. There’s going to be some process to this.
Rob 08:45
There’s going to be some things we’re going to have to work on, but in about six weeks, we’re going to see that disappear. That could have been a whole different conversation. So the other question that maybe Ken could have asked, and then there’s a bunch of other questions too.
Rob 08:57
The other question that Ken could have asked is, when did this person want to fix their swing by? Obviously, the member guest tournament was coming up, but maybe that wasn’t the time that they wanted to have it done by, right? So just by asking, hey, when were you hoping to get started? That could have led to a whole different conversation.
Rob 09:09
And that follow up question of, is there a reason you’re trying to do this now? What is this? What is it? Why are you trying to do this now? I’m just trying to understand to me, if there’s no deadline and there’s no pain, there’s literally no sale, it’s never going to happen. They have to have a deadline, or they have to have pain, or they have to have a combination of the two, or there’s it’s just going to go nowhere.
Rob 09:32
And I think the last piece that I would interject here for Ken would be and we talked he and I talked about a few other situations and things that he could do to improve this. And if you’re interested in this kind of information and you want to get some help because you’ve run into something similar to this, or you’ve had some other situations that come up in sales and you need some help, call me. I’m this is what we’re here for. I’m here to help you work through those sales processes and improve every time.
Rob 09:56
So the other thing that he should be talking or thinking about is the DISC profile. What was this guy’s DISC profile? Because the guy was relaxed. They were doing a little bit of work together, right? So, Ken could have determined whether or not this person was a high D and high I, or an S or a C.
Rob 10:12
He could have figured that out after a little bit of conversation. If he was paying attention. Did he do that? It didn’t sound like he had done that. What he did was he thought this person was a high i, because they were so energetic and they were outgoing, and they kind of felt like a good connection right away. But did he validate that? And did he figure out, yes, that is actually the type of personality this person has. I mean, if this guy was a high I, final through isn’t always one of their strongest suits, unless it’s paired with a D.
Rob 10:39
So there’s some issues there where you could run into maybe that’s just part of the process. What if they’re an S and they can’t make any decisions without getting help with other people? All of that are contributing factors to help you understand or determine whether or not that person is going to make some decisions quickly or slowly, and if they’re task oriented, people oriented, and so forth, all of those pieces all fit together, in addition to you helping them discover the pain that they have and making sure that they understand that the pain that you’re trying to solve is going to be fixable.
Rob 11:07
And so all of those pieces just didn’t happen very well for Kent. So, if you’ve ever had a prospect ghost you after a conversation, let me tell you, you’re not alone. But here’s the thing, most salespeople miss the real reason that it happens. They assume that the interest is there, they have the intent. They’re going to do it, but the reality is they are not going to do it.
Rob 11:26
If you are ready to stop kind of guessing and start figuring out the real answers from your prospects, that’s where I come in. Through one-to-one coaching and team sessions, I can help you ask better questions, uncover actual buying motives and avoid waste of time chasing the wrong leads. You want to close more sales with less pressure? Let’s talk.
Rob 11:42
You can contact us at Questions@TheSlowPitch.com. Listen. What it comes down to is you don’t need more leads. You need better conversations, which also means better questions until next time, Slow Down and Close More.
V/O 11:55
Thank you for listening to The Slow Pitch. Do you have a question about sales? Call or text your question at (608) 708-SLOW. That’s (608) 708-7569. Or you can email them to Questions@TheSlowPitch.com, Slow Down and Close More.