


30 Sep 2026 · 10m · 3 chapters

Sales discovery mistakes that kill trust, especially in advertising; how to replace “pain-point” interrogation with trust-building discovery and value bridging.
Laura, an advertising salesperson for a small community magazine in Durango, Colorado (about 1,700 businesses; real estate agents facing a flatter market with 239 homes and 400+ agents). Jeb Blount (host; author of Sales EQ; sales trainer).
Don’t “share their pain” or lead with pain questions; prospects sense it’s self-serving and may wall off. Trust is earned by listening, making prospects feel important, and showing you understand them. Focus on what motivates them, then bridge to your solution.
Real estate agent Angie—ads helped her pick up five listings in one month, restoring confidence and control.
Written by AI. May contain mistakes.
Discussing the importance of discovering pain points in sales.
“If they're not sharing their pain with us, maybe we haven't earned it yet, but we don't have a lot of time.”
Exploring the significance of trust and relationships in sales.
“But if you actually go talk to people, they don't feel like they're doing so great.”
Identifying the critical decisions clients make in the sales process.
“That's plod.ai forward slash jeb and use code JEB to get 10 % off your purchase.”

Get the gist, explore an idea or ask about something said.
On Sales Gravy: Jeb Blount, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00This is the Sales Gravy Podcast. Hi, I'm Jeb Blount, bestselling author, fanatical prospecting, objections, sales EQ, and inked, and I'm here to help you open more doors, close bigger deals, and rock your commission check. Hi, Jeb. I absolutely love your stuff. I've read many of your books and have learned a lot about what I have been doing wrong for all these years, especially like the EQ book. Wow. I just read that one recently and I was like, wow. I sell advertising in a small community magazine. I'm talking small mountain town, like 1700 businesses here total. But here's my question. So when we're talking about doing discovery with a client and trying to get them to share with us their pain points so that we can solve their problems, If they're not sharing their pain with us, maybe we haven't earned it yet, but we don't have a lot of time.
0:56Is it appropriate to kind of share their pain with them? For instance, right now in my market, our realtors have been so blessed with not having to really fight for business because it was just falling out of trees here for homes. But now the market, because of the interest rates, has gone flat. There's only 239 homes on the market and over 400 agents. Would that be appropriate? Let me ask you a couple of questions. What mountain town? Durango, Colorado. I was just in Durango, Colorado last week. You didn't come see me. I would have found you. Beautiful, beautiful, beautiful city. So small mountain town, Durango, but you have a regional airport, so you're not that small.
1:36Let me take you back to Sales EQ. So you read Sales EQ. What was your biggest takeaway from the book itself? Really slowing down my process to take time to get to know the person to earn that trust. And our company wants to make this transaction really quick. Like their processes don't even go in and ask questions, just start your presentation. And that works sometimes, but not all the time, not most of the time. So that's what I've learned is I have to really step back and build that trust and relationship. And that matters because when you think about the market that we're in right now, so Durango is a happening town.
2:15It's a really nice town. Just all the growth is there. But we're still in an economy that on one hand, like it feels like if you look at the statistic, it looks like it's doing great. But if you actually go talk to people, they don't feel like they're doing so great. And because you have this uncertainty in the market and a little bit of volatility, when you're out selling advertising to businesses or to real estate agents, especially real estate agents is having a hard time even selling or listing a house right now because of the insurance rates, they're holding back. So that trust absolutely matters because you sell an intangible.
2:43And they have so many different options and places where they can spend their advertising dollars. So if you don't build trust, it's hard to get them to spend with you once, but then what you really want is you want the advertiser that keeps on spending. They keep every copy that you put out, they're in it. If you think about what you just asked, which is, let me ask about their pain points. That's one reason why people buy advertising, pain. They feel something. But another reason people feel advertising is they're aspirational. So another reason people buy advertising is they're egotistical.
3:12Another reason people buy advertising is that they're building their brand and they want more brand awareness. And one of the problems when we think about pain is that we go in and we direct our questioning specifically about pain. That questioning, that discovery comes off sounding self-serving and it can lead to leading questions. And here's the thing about the people that you're selling to. If you're in a conversation and they're not opening up about their pain, they probably sense that the moment that they open up about their pain, that you're going to be using it against them to close them.
3:41They end up putting a wall up and they hold back. So what I want you to do is think about a little bit of a different approach. And it sounds like you've got most of it, but... Going into a follow-up call, I want every important note right at my fingertips, not buried somewhere in a scribbled stack of notes. And with Plod Notepin S, I always have them because it's a wearable, portable note taker that lets me stay present and focused on customers during every single meeting. Plod captures the conversation and turns it into organized summaries and action items so I can follow up faster. And if I need a specific detail, Plod's recall has that ready for me.
4:15And that's why Jeb Sr. and I and all of Sales Gravy trusts our Plod Notepin S. Try Plod and stay focused on the conversation while it handles all of your notes. Go to plod.ai forward slash Jeb. That's plod.ai forward slash jeb and use code JEB to get 10 % off your purchase. Think about five decisions that people make before they decide to give you money. Decision number one is, do I like you? Part of that's like, you know, you're a likable person. You're asking me questions. You said, I read your book. Like you own me at that moment. So I love you too. And then we have something in common. I was in your town.
4:49You live in that town. So there's a couple of things. We talked about those things, but if you think about it, likability of things you can control, like this person look at you and say, I just didn't even like her face. Like people say that sometimes, but mostly likability is how people interact with you. So when they say there's only one chance to make a first impression, they're actually wrong. Someone cannot like you on the first impression, but once you start listening to them and spending time with them, people have a tendency to like you and they lean into you. So the easiest way to be likable is to listen to someone.
5:17The first two questions and the first two decisions are do I like you? That's number one. Number two is do you listen to me? Now, the easiest way to be likable, think about any relationship in your life, the people who listen to you are most likable. Now, think about what you said. My company says it's transactional, just go in and pitch. Well, think about the person that you like the least. It's almost always the person standing in front of you talking about themselves, even the ones on social media, like the ones that are only talking about themselves, talking about themselves, talking about themselves.
5:43Those are the people you don't like. So the easiest way to be likable is to sit down and listen to somebody. Tell me your story. Tell me what's happening in your world. This is important for you, Laura, because you have one thing going against you, and that is that you sell advertising. Think about people who sell advertising and people who sell insurance. It's a repellent to human beings, right? So that way that you ease into that conversation and get them telling their story really matters. You start asking questions about the person, like what's happening in your market right now? What's happening in real estate?
6:10How are you handling the fact that there aren't as many houses listed and there's so many people competing for them? So rather than telling them their pain or feeding them their pain, just ask questions about the things that you sense that they're probably dealing with and allow them to tell their story. The third decision people make is, do you make me feel important? Every human being has an insatiable need to feel like we matter. They want to know, am I important to you or am I a person that you care about? If you're just transacting people, it doesn't make people feel that way. If you think about it like this, the easiest way to make someone feel like they matter is to give them your time and attention, to just listen to them.
6:44And in fact, when you just listen to another human being, you give them the greatest gift that you can give another person. And that matters because, and especially in advertising, you're asking them to move to the next step. You're asking them to give you more information. You're asking them to give you money. So the more that they feel like you make them feel important, the more likely they are to accede to a next step. The third decision they're making is, do you understand me? Do you get me? And that's why a focus on pain is such a mistake. It's a focus on what's important to them. It's a focus on what's driving them, what's motivating them, what they're concerned about.
7:16Some of that is essentially pain. Like it's a gap that you need to feel. More important is that they're able to say that you get and understand me. And so that's where you really earn your chops. Like, especially in advertising, this is where you close. And that is through what we call value bridging. All that is, is we talked about, you know, bridging in sales EQ, but it's okay. Here's where you are right now. Here's the situation and here's what you want. Here's what you feel. Here's what you're motivated for. Here's what's driving you. Here's how we can solve that problem. So it's just a value bridge.
7:45And you're saying, Laura, you told me this, this, this, and this, and this is exactly how we can do this. Now, one thing I might encourage you to do, especially when you're selling advertising locally in a small community, is to have some micro stories available to you. And micro story is a way for you to sell the value that you deliver through someone else. Again, advertising, a lot of people have options. It's a really tough sell. It's the hardest sell, I think other than maybe insurance, it's business to business. Advertising, hands down, is the hardest sell there is. So what you want to be able to say is I was working with Angie.
8:16She's a local real estate agent. And she expressed that she was having some problems with finding enough listings because there's so many real estate agents out there competing. And so when there's only a handful of people who are listing their homes because they're trying to hold on to their current interest rates, it makes sense that you're out there and your face is out there. So we ran this ad for her. Here's the ad. And she picked up five listings in the same month that we ran this ad. And what that's done for her business is given her confidence back. It's put her in a situation where she's now in control of her market.
8:47And I want the same thing for you. So you build a value bridge that way. The last decision that people make before they give you money is, do I trust and believe you? So you talked about this trust earlier. And the way that you earn trust is demonstrating that I truly understand you, or at least I'm trying to understand you. And that's where when you said transaction and pain, when I hear focus on pain points, all I hear is you're just transacting me. And in fact, I did a video a while back on this. I had a rep who called me who actually said, what are your pain points? Like they asked me that question.
9:16I'm like, who taught you that? Who would tell you to ask me a question? It's so self-serving. So rather than having this, I gotta go focus on pain, forget about that. What you wanna focus on is the human being that's in front of you. The decisions they're making before they do business with you is do I like you? Do you listen to me? Do you make me feel important? Do you get me in my problems? Do you understand me? And do I trust and believe you? The good news, Laura, is that you read Sales EQ, so you have a pretty good foundation and basis in this process of this philosophy. But more than anything, my bet is that you're a great conversationalist and you're a person that people really like.
9:49So use that strength that you currently have and that you know you have. Like leverage that and just get into a conversation with people and they're gonna say, this is something I'm trying to solve or this is an issue out here. And as long as you can connect the dots between what you do at your magazine from an advertising standpoint and how you can help them achieve that goal, you're going to win.
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When prospects won't share their pain, pushing harder only raises the wall.
In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers a question from Laura, who sells advertising in a crowded local market. Jeb explains why pain-focused discovery sounds self-serving and walks through the five decisions buyers make before they give you money.
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