Sales isn’t about talking more—it’s about understanding why people say yes.
In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down the sales psychology behind closing high-ticket deals—especially in industries where trust, risk, and certainty matter most.
They challenge the idea that great salespeople are extroverts, unpack why emotional intelligence beats raw IQ, and explain how top performers position themselves as the “safe choice” in high-stakes decisions.
From uncovering real buyer motivations to building authority and confidence, this episode is a tactical deep dive into what actually drives deals across the finish line.
In this episode:
- Why high-ticket sales is driven by emotion—not logic
- The role of fear, risk, and “playing it safe” in buying decisions
- How to uncover what really matters to your customer
- Why “What’s your biggest pain point?” is the wrong question
If you sell anything high-value—or want to—this is your playbook for closing with confidence.
More Entry & Exit — https://www.entryandexit.co/
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People think that being a high ticket sales closer is about being a better talker. And it's really not. Hot take.
I don't think you have to be an extrovert to be in sales. And so they've got, you know, kind of the emotional intelligence, emotional awareness to be able to navigate what people are feeling. Like I hate when sales guys go, what's your biggest pain point?
It's like, yo, you're asking that question, you're taking the shortcut, and like you're not going to get any valuable information out of it, and you're just going to annoy the customer.
But in our industry, it's like even more important when you're touching life safety, we're serving schools and universities. We really have to give them a high degree of certainty in what we're selling them.
Welcome to Entry and Exit. My name is Steven Ullman, and this is Colin Trimble, my less attractive co-host. Today we're going to be talking about sales psychology that actually closes deals and hopefully big deals. Because we like big deals and we can't lie.
We cannot lie. I think everybody should know that Steven really wants to open this with saying welcome back. But we were told we can't say that. So welcome back. If you've listened before, welcome back. Welcome back. Or if it's your first time listening, welcome for the first time. We're glad you're here. And we'd love it if you like and subscribe, by the way. We're just gonna lead with that. Please. Um, all right. Here's the thing, folks. People think that being a high-ticket sales closer is about being a better talker, and it's really not. I really don't think it is. I think that you I don't even think, Steven, hot take. I don't think you have to be an extrovert to be in sales. Absolutely not. No, I think I would even argue that I, although I am very outgoing, I am not a full extrovert. I really I am more of an introvert. Um you are a thoroughbred extrovert. Wow. But I am not.
Um and here's what I would say Um being a high-ticket sales closer is understanding why people say yes, uh, and why people always end up um kind of reverting to the safe decision and not the decision that maybe makes the quote most sense logically. I think a lot of people don't realize that sales is a lot more about emotions um than it is about logic.
Yes, that's why you see a lot of sales guys that have had incredible success that you know, maybe their friends are surprised that they've had so much success because they didn't think that they were really that smart.
Yeah.
They aren't high IQ, they're high EQ. They're high EQ. And so they've got, you know, kind of the emotional intelligence, emotional awareness to be able to navigate what people are feeling, what people think they need, what you know, fears or excitement they have.
Yeah, I think like logic kind of explains the decision, but emotion is ultimately the thing that makes
the decision. People always say, like, we've heard this before, like when you first started in sales, it's like uh nobody ever got fired for buying an IBM. And that's because they IBM wasn't even the best solution, but it was like the safe bet. Right. And so um you've gotta position yourself as the safe bet uh in order to be able to like get the customer over the hump. Sometimes it's like I've heard this before being in sales, like, man, I really want to go with you guys. You've got the best price, your product is great. I love working with you, but like, man, Oracle's been around forever, and we just like our company just really feels like that's the lowest risk option. Dude, and I've made that decision before. Like, we've needed to make decisions on certain software or certain vendors, it's just like, ah, I really like that guy. I really want to kind of, but I just my danger flag is popping up because it's really more about like fear of loss, don't you think? Like when you're making decisions, especially big ticket purchase decisions, you're willing to take risks on lower ticket purchase decision, which that's an interesting nuance because I think that some people um people's perception of high ticket and low ticket is totally different. If I'm if we're selling to a daycare and it's five thousand dollars, that's a high ticket sale to them. Yep. But if I'm selling to one of our largest enterprise clients, this is a change order that's not even going on anybody's radar. You know? So it's like it really depends on what is their perception of high ticket, and then you gotta have to reframe around that, right?
Yeah, it's a lot of that on the high ticket stuff is risk mitigation, like you're saying. And then going back to the concept of being high EQ, like to be able to contextualize to that customer who they are, what their budget is, things like that, and and how you might sell to them, it's it can be the exact same solution sold very differently.
Yeah, I think a lot of times salespeople are trying to find ways to convince the customer to buy their solution, and really what they need to be looking for are ways that a deal is gonna not happen. And what you really want to understand is what is the the biggest fear for the customer? Like, I hate when sales guys goes, What's your biggest pain point? It's like, yo, if you're asking that question, you're taking the shortcut, and like you're not gonna get any valuable information out of it, and you're just gonna annoy the customer. What you really want to understand is is this decision driven by fear of loss of money or revenue, or is it driven by fear of loss of time? Sometimes for me, I'm not really concerned about blowing $10,000. I'm more concerned about how much time this is gonna actually take from me and my team. Right. Um, and so sometimes hitting the easy button, spending more money because it's gonna because even though I think your solution is great, but I'm like a little worried about how involved it's gonna be for my team, I'm gonna go with the more expensive solution that maybe isn't even the one I love as much. But I just really don't want to the risk reward. So you've kind of got to get into the psychology of the person in the security world, like a theft of risk or theft of loss is like a huge thing for us. So we're always sort of evaluating like what happens if, right? And then in like general business worlds, like lost revenue, lost time, right? So, like, are you if you're selling uh, you know, any other solution, if you're selling garage doors, it's like, okay, well, you know, what happens if this thing breaks in six months from now?
Yeah.
You know, yeah, my solution's more expensive, but I'm gonna be the guy that's gonna be out here in an hour if it breaks. You know, so you have a garage door that works or whatever.
I along
those lines, I think a lot of it comes down to needing certainty. So everybody wants to have confidence in their the decision they're making, the buying decision. But in our industry, it's like even more important when you're touching life safety, we're serving schools and universities and city of and all sorts of stuff like that. I mean, we really have to give them a high degree of certainty in what we're selling them. Um, and so that's that's going to be a big determining factor, but even that specific element is also contextualized based on who that customer is or what solution you're selling. Yeah.
Yeah. Yeah. And I think one creative way we've done that is we've done social proof. Yeah. In our sales process. So it's like, hey, yeah, talk to our customer. Uh the best way for you to know how we're gonna do is talk to a customer that's already spent money with us. Um, and I think also projecting confidence really helps. Um, that's I think that's honestly, man, like the guy that used to own Alarm Masters, Brian Turner, shout out, great guy. Um customers loved him. He didn't, he didn't have a sales process, he didn't have uh, he didn't do any outbound, but he was so incredibly knowledgeable that he was educating the customer. And sometimes the customer, like it, like it didn't work on every customer, but generally speaking, it was pretty knock it out of the park effective because he had this like expert authority vibe that made customers feel like, okay, I'm gonna go with you because I'm confident that if I go with you, um, like I'm confident that if I go with you, that you're gonna get it done. Like you know what you're talking about, you're gonna step in if there's a problem. Like, I'm not gonna rely on somebody else, which I think goes a long way.
And the more risk or the more um, what's the right word? Like the the more that's on the line tied to that buying decision, the more someone needs to see that level of expertise. You know, it's like, oh, you know, I'm asking someone like which gum to buy, you know, what their opinion is. Like, oh, is that flavor good? Like, not a lot on the line there. I mean, I'm a little particular about the chewing gum, but yeah, it's not life safety. So right. Yeah.
Yeah, I
think I think authority sort of changes everything. Uh, you know, buyers they don't want options, they want you to give them the the thing, they want you to give them the recommendation, you know. Like one of my biggest pet peeves again is when sales guys say, I've got three options for you. You pick, and it's like, I'm opening my coat of snake oil and you can decide which one you want. It's like, no, dude, we're getting hired to be the ones to tell the customer what we think based on our years of experience and the fact that we do this every day, that this is the solution they should go with. And in fact, when they push back on you and say, I want to go with something cheaper, you say no. Right. Because you're so confident in your solution that you're not willing to budge. That inspires confidence. I've had customers say, Hey, we don't want to do that. We don't want to do the cloud solution, give us something cheaper. And we said, no, we we don't want to sell you a solution that's gonna put you at risk because that's ultimately gonna lead to a damaged relationship with us. So we would rather just not quote you anything else. And we can, but your solution demands this, you know, this product or whatever. And so I think it's using that. The other thing I like, one of the things I um I tell our sales guys all the time is like, hey, you know more about security in our case or fire than the customer does. But you're gonna get asked questions you don't know the answer to. And the way to respond is, hey, I think I know the answer to that, but I don't want to give you the wrong answer. Let me go validate this first and I'll come back to you in 24 hours. And the customer's gonna be good with that. That's great.
That's a another small thing, is like specificity wins, you know. So, hey, I don't know the answer, but let me find out is not as good as I don't know the answer, let me find out, and I'll get back to you today, or I'll get back to you in the next 24 hours. Just those little small little touches of specificity. Um, even like hard numbers, talking about like case studies or testimonials, anything specific you can tell someone, you know, we're selling to a multi-location site. Hey, you can talk to our other 14 location customer, like any elements of specificity are those small little deposits in in that kind of confidence button. Authority. Yeah, authority.
Yeah.
Um,
I think framing the decision is really important of like what and and dude, we asked this question during our sales process in the discovery is we're always trying to figure out what's the compelling event. Or if you're using Bant criteria, it's the need and timeline. It's kind of a combination of those. And and at Salesforce, they used to say to us all the time, like, hey, if you don't have a compelling event, your deal's not getting done. I don't care. Like, you've got to have a budget, you've got to be connected to power, and you've got to have a compelling event. And if you don't have those things, you're not closing the deal. Um, or at least we're not gonna forecast it. And so we're always, and I think that people understand the value, it's understanding budget is really tangible and understanding power is really tangible, and people get that, or sales, most sales folks do. But I think what's lost in the industry is this idea of getting a compelling event of like, what happens if you don't do this today? That's a question that I ask customers during Discovery. Or another question would be um, why are you doing this today? Why did you not do it six weeks ago? And why are you not doing it six weeks from today? And if you ask that question, some really interesting things are going to come out of it. Well, we just kind of want to, or whatever. It's like, okay, well, they're not super motivated right now, which may mean you're not you shouldn't spend time on that. You know, high-ticket sales is about finding an opportunity that's likely to close. Not like high ticket sales by nature is not high volume. It's high touch, low volume. That's right. Yeah, I think I think honestly, the the closeout for me on all this would be fear is the the biggest driver of action. Um, fear of loss is like the ultimate thing. If you've ever sat in a sales training, it's like fear of loss, your biggest competitor is nothing, then the customer doing nothing. That's your biggest competitor. Um, and so I think showing authority, showing them that you are the safe option, those are the things that drive drive the real value.
But we have done a really good job at implementing this and and teaching this, especially over the last two years, and it's really paying dividends. Um, so yeah, it's kind of living proof.
If like if you guys, the listeners, if you understand this, high-ticket sales is really gonna stop feeling like you're actually selling and it's gonna start feeling like predictable revenue. Yeah. Uh, because you're gonna start to see a forecast. Like, how amazing would it be to be able to know that, like, hey, I'm I I am 75% or more confident in these deals, and I'm less than 75% confident in those deals. That's gonna help you make better business decisions. So, um, man, if you want more of this kind of content, subscribe. Like we are talking about sales stuff all the time. It's my biggest passion. I love it. Uh, we'd love it and appreciate it if you'd like and subscribe. And thanks for listening. Appreciate it.
