5 Tips For Salespeople (pt 4) Pain Questions

Sales podcast ep 66 the slow pitch pain questions
Sales Podcast, The Slow Pitch
The Slow Pitch Sales Podcast
5 Tips For Salespeople (pt 4) Pain Questions


Ask Better Pain Questions to Get More Sales

To close more sales, you must ask better pain questions. But the question is, how do you ask better pain questions in sales? Since we’ve already covered you must go for the no, it’s time to get into asking better pain questions to get more sales. If you’re looking to close the sale and they’re not closing, we’d recommend starting at the beginning of this five part series. You’ll find that asking better questions in sales will get you more sales.

Let’s start with why pain questions are important and why they’re better questions than letting the prospect tell you what they want. Great pain questions include getting to know the prospect better, getting to understand the problems they’re having, and understanding how it’s affecting them in the business as well as personally.

This may not seem like that important, but the more you know about these pains and how they are affecting the prospect, the better you know how important the product or services you are selling is to them. The more important it is for them, the more likely you’ll close the deal.

A couple of the pain questions from this episode were:

  • Tell me why this is happening?
  • Tell me why this is important (now)?
  • How much is this costing you?
    • Time?
    • Money?
    • Is this normal for your business? for the industry?
    • How does this relate to the size of the business?
  • What do you hope I can / we can do for you?
  • What is your expected timeline? Why?
  • How has this affected you personally?

These questions will get you a lot closer to a sale than if you let them tell you why they need your service.


Podcast recorded on Squadcast.fm

Related Episodes: 

How to Find Pain in Sales. What Is Pain in Sales?

When a Potential Client Says Your Price Is Too High – How To Respond Role Play

Other Ways to Find Customer Pain Points



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  0:08
Welcome back, everybody to The Slow Pitch. And this is part four of the top five tips for salespeople. And today where you’re going to talk a little bit more about pain, and you’re probably like, What in the world? We just did that? That was number one part of part one of this, what what are we doing? We’re gonna dig a little bit more into that.

V/O 0:25
You’re listening to The Slow Pitch Podcast, a podcast about selling less and closing more.

Rob  0:32
Alright, you’re probably asking, Why is this list contain the word pain twice? I mean, it was part one. And now we’re talking about in part four. And so my question back to you, why do you think it’s on here twice? Why do you think that pain was so important that I put it on this list twice, think about that. It’s that important. That’s why if you don’t have the pain that you need to have to know whether or not they’re got the bleeding neck, and they’re gonna go forward or not, and all that stuff, you’re not going to have what you need.

Rob  1:01
That said, we’re going to the purpose of this episode is to get into the questions of what you should be asking so that you get these pain numbers and information out of them. So you’ve done all the pre work, you’ve kind of done a little research, you’ve had the initial conversations with them when you first sat down. Now it’s time to dig into these pain questions. And they’ve said, This is my problem. So I’m going to rattle off a couple of different questions. And if you’re driving, there are going to be in the show notes. So just know that I’ll have them in the show notes as well. But the point of this is, these are questions that will get to become more and more personal for the individual you’re talking to. And the reason that happens, is because if it’s not really impacting them personally, or how affecting them personally, why are they even motivated to do it?

Rob  1:44
Now, I’ve had conversations with somebody where they say, well, it doesn’t really affect me personally. But it does affect the business enough that I need to fix it. Because eventually, it’s going to affect them, right? You know, if it’s financial problem, it’ll affect that person who’s embedded in that role? Who’s supposed to fix that? Right? So let’s get these questions.

Rob  2:01
First. These are the questions you want to ask when you want to start getting into the pain. So tell me more about what’s happening. Tell me what’s happening. Why is this important? You know, those types of things to get the high level stuff, and you’re going to do? Those are typically the questions a lot of people are good at asking, and can do it pretty well.

Rob  2:18
The next question becomes, like how, at some point, you’re gonna have to talk about, you know, how much is this costing you? Because it sounds like it might be affecting some of the numbers here. And they may say, you know, it’s not costing as much it’s costing this much, whatever, whatever their answer is, but whenever whatever their answer is, you need to make sure they’re answering in terms of a couple different formats.

Rob  2:40

One is, financially, how much is this costing you, but you also have to keep in mind that it could be costing them time, it could be costing them extra energy, they may have to put extra resources on this problem until they fix the problem. And so that’s where you have to think about costing them and have to ask the question, is this costing you that much in financial? Well, tell me how much does this you know how much time you effort and effort you put into this? Because when they start telling you a financials, and you ask the question about how much time and effort they go, Oh, time Oh, my goodness, we’re spending hours on this. Okay, well, ours, like what level? Are you talking about entry level, you know, $8 an hour person to another person? Are you talking about like executive level? And if they start to realize its executive level, it could be getting very expensive very quickly. We didn’t even think about those numbers. Right. So that’s one thing.

Rob  3:27
Second piece is okay, well, this number that they’ve thrown out, is this per month, per week, per year, per hour per watt. How, like, what, what’s the, what’s the reference point for time? And so you don’t have to ask them when they tell you it’s, you know, it’s cost me 1000 bucks, 1000 bucks, what per order is this per, per week, per month per year? Like ask that question? What do you what do you mean by $1,000? Where is that? How do you figure that number? It made me tell you that but make sure that you understand that? And then the other question, I think is always really important for you to ask after they get into the numbers a little bit is to start to ask about the relative peace.

Rob  4:02
So you know, I noticed your business is $100 million sales operation. And you’re telling me this cost you $1,000 And you said it was every month? I mean, that doesn’t seem like it’s gonna affect you guys very much. Like who cares right? I mean, like, why is this a big deal? Or you know, they’re a million dollar business million dollar a year business and it’s affecting them it’s $1,000 a day okay, now you’re bleeding a little bit let’s let’s talk what what do you why is this why is this happening? You know, that kind of thing. But find out, is this normal? Is this normal for the industry? Is that expected not expected? You just trying to narrow it down a little bit more like that kind of stuff?

Rob  4:41
And then you might ask something like, have you tried to fix this already? How long have you been trying that? Did when you did try it? How did it work? What what didn’t work? What did work? You know, start getting them to help you understand what they’ve done in already to resolve their problem. And then what are you hoping that I might be able to help you with? So that’s a question and that you’re having them explain to you what they think you can do for them. And this is important, because if they tell you, we’ll expect you to get this done. And you ask the question, well, how how long do you expect that to take? Like, what do you expect you expect managers done by tomorrow or next week?

Rob  5:17
Or if they say, No, I, you know, this is a two week project, we think you should be able to get this done in two weeks, but it’s really a like a six month problem, then there’s a disconnect there. And you need to help fix that by asking some more questions and say, How did you come up with the two weeks? Why do you think that work? You know, was there a reason that that that was the number that you were thinking about in terms of time? What if I said that I couldn’t do it that amount of time? Like, that’s, that would not be a normal timeframe for something like that for us? What would what would you say? Then you know, what? That kind of thing makes them understand that they may be wrong, and they have misinformation somehow that they’ve gotten, or they just didn’t know. And that’s okay.

Rob  5:53
So and then the other question that you might start to ask is, like, hey, let’s fast forward, we’ve done what you want, we fix it, what does that look like? It? Does their picture match what you think it should be? That’s a very critical piece, it kind of adds to that last question. Right? And then the other question I would ask is, like, how is this kind of impacted you personally? So when you talk about these numbers? I mean, that’s, that’s, uh, you know, you’re telling me that’s a lot for your business. And it’s going to be stressing you out a little bit, right? Yeah, yeah, it’s stressing me. I don’t know. You know, I don’t, I don’t know what I’m going to do here. i This is this is this is major. And it sounds stressful, right. And you let them feel that feeling of stress, you have to listen for emotional keywords from them.

Rob  6:33
They’re like frustrated, they’re stressed out, they’re, they’re worried about something they’re really concerned about it, or they’re upset about it, you know that those are the words you’re listening for from them. The now you’ve gotten some pain now, you know, that’s where they are? And are they speaking to you? Are they speaking more than you are, because they should be?

Rob  6:53
This is the point where they should be doing almost all the talking, your job is to start to listen, and really let them let it out. You’re kind of like a psychologist almost like, let them work through their problems emotionally, a little bit, and asking the right questions to let them work through that. And then when you get to that point, where you have found enough pain, because you know, what the money relationship is there, how much that’s costing them, and so forth. The time and other resources, you know, all that stuff.

Rob  7:23
You’ve asked all the who’s the what’s the when’s the where’s the house, the wise, you’re acting as stupid as possibly like a Reporter Out there, you’re just collecting information, you’ve gone through all of that, and they’re kind of in this state of they’re there. They’re worried they’re concerned. And now is the time you say something along the lines of?

Rob  7:45
Yeah, I know, it’s, I’ve heard this before. And, you know, there’s a lot of companies that we deal with that have the same similar type of things. And that’s, that is what we do. I just want you to know that you’re not alone in this, and that you’re not the only people that have this problem. And it’s not the last time we’ve heard this and not the last time we probably ever fix it. And whether we work together or not, I just want you to know that that’s this is something that a lot of people are struggling with.

Rob  8:12
Because they want them to understand that you’re there for them, and they want them to feel the support. And that you’re kind of you’re ready to help them. Right. And then at some point in that process, your conversation can easily go to what do you what do you want to do next? And then they may say, well, we should probably talk a little bit about much is how much is gonna run? Like, what is this gonna take?

Rob  8:32
And that’s really kind of what your next step is anyway, right? So you might say something like, you know, when you get into the budget thing, you might ask him even like, what’s, what’s the, you know, what, what are you looking to put aside for this? What kind of investment did you have in mind for something like this? This is the time for the pain of the budget question. This is not the earlier is not after all this, they’re in that emotional state. This is the time to ask, you know, what was your expectation? Or when you’ve done stuff like this before? What’s your expectation? If you’re a web developer, you’re trying to sell a website, right?

Rob  9:03
And you’ve you’ve got them in this understanding of well, how important it is they’ve gone through all these questions. And now they’re like, ready to buy and the and you say, Well, you know, when you’ve done this before, how much did this run you and they go, you know, last time it did this, you know, it was 100 bucks to make my website, and you know, you’re gonna be 5000. And now’s your chance to say, Boy, you know, $100? Well, I mean, maybe that’s, that’s all you should be spending it, or were you happy with the website that you had? No, I’m not happy, okay.

Rob  9:31
And so you start working them through the understanding, it’s going to cost more than that right for them. And so he said, Well, you know, how much have you heard of others? Have you heard of anybody else investing in their website when it runs these days? And you start asking some of those questions and if they want to answer and they don’t give you that, you know, my you might be able to give them a little bit of a selection options like, Hey, we’ve built websites between, you know, 2004 1005 1000 8000, and we’ve done 10,000 And up but I don’t know what range you’re even thinking now. You’ve got them that you what you’re trying to do is get them to give you a number because that’s really what you want.

Rob  10:03
And I’ve had it where somebody tells you that it’s a number that’s different than what you expected from both ends. I’ve had somebody say, Well, I expect to be 500, when it’s 5000. And I’ve heard somebody say, it’s 20,000, when it’s really 5000. And so now you’re gonna have to address that as well. And the way that you address that is with another question, too. What if I said, I couldn’t do that for that amount?

Rob  10:24
And by asking that question, they may say, Well, what do you mean, and you need to explain a little bit of that. So when it was 20,000, when it’s actually five? What if I said I couldn’t, I couldn’t charge you 20,000 For that, because it’s not gonna take that much that much effort in that time that that work. But that does mean that you could probably adjust your price up a little bit, right? Because if it’s normally going to be 5000, for you, and it’s a big client, they can they can afford to spend a little bit more because they know that that’s what it’s going to take.

Rob  10:51
And you also understand that in this pain questions, that there’s going to be an impact that’s going to have on them, then maybe it’s 10,000, you’re going to end up charging, right. That’s where you end up finding out what those numbers are. And you can start to charge the appropriate amount. I hope this episode helps. We haven’t really dug into the pain as much as this in some of these other episodes, but it is where you need to be focusing.

Rob 11:12
That’s why it’s on this series twice, because it’s that important. And the more you dig into these questions, the more information you’ll be able to get out of them. And the more that the you’ll be able to understand what their issues are, and they will feel very comfortable working and moving forward with you. If you have questions, we’d love to have them, email us tweet to us. We’d love to hear you guys and hear understand what you’re looking for. I hope that helps. And our next episode is going to be the last of the five part series for top five tips for salespeople. And the title of that is going to be about tracking numbers. And there’s an important reason why you have to listen to this if you’ve gotten this far. Until next time, Slow Down and Close More.

V/O 11:52
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.

Rob  12:42
Thanks as always, for listening today. If you’d like this podcast, please subscribe and leave us a review. We really appreciate it. Follow us on Twitter, Instagram and Facebook at The Slow Pitch. We were mixed today as always by Johnny Polakis. And we were produced by High Gravity Studios. Music credits and other notes are in the show notes section on TheSlowPitch.com And we’ll be back with another episode soon.


Leave a Comment