Improving Your Sales Skills as a Freight Broker | Episode 308

Freight 360

August 22, 2025

Top freight sales pros don’t win with flashy pitches or closing tricks—they succeed by truly listening. This episode shows how strategic questioning, genuine curiosity, and overcoming ego-driven barriers create the trust and understanding that drive lasting customer relationships.

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Show Transcript

See full episode transcriptTranscript is autogenerated by AI

Speaker 1: 0:19

Welcome back. It's another episode of Freight 360. We're going to talk some sales stuff today, but first make sure to check out all of our other content and share us with your friends. Leave those comments and questions either in YouTube comments or through the website. We did have some come through this last week and we'll be answering them on our final mile segment. So always make sure to tune in on Tuesdays or whenever you get a chance to catch up and we'll get to your Q&A. Check out the Freight Broker Basics course on our website if you're looking for educational options for your team or just for yourself to start and grow your brokerage. Ben, we're getting towards what feels like the end of summer, even though we're technically only like we got like another month or so left. But it feels like you know. I don't know, maybe not in Florida, where it's probably 90 degrees every day still, but dude, it's so hot, but I'm so excited for the fall.

Speaker 2: 1:09

Ava's been in school for a week and a half now. She went back last Monday. It's awesome, like she loves riding the bus. It's her first time riding the bus, so it's super cute watching them, you know, get on the bus for the first time, like she's super excited. But I cannot wait for the weather to break too. It is just 94 every day, no rain, lentiless humidity, and I'm just like I can't wait for it to like cool down.

Speaker 1: 1:33

we just got like a break in the heat, like it's been really really hot.

Speaker 1: 1:37

Um, I think like july and the beginning of august was like one of the driest summers I've had in a while up here and we finally just start getting some rain as of like Sunday, and it's rained like every day and it's kind of nice because I just my grass is turning green again and I had grass planted this year because I had some landscaping stuff ripped out and it's finally like filling it. So a nice little break for about a week or so, it's, it's nice, but I still want, I want that push of the last bit of summer before inevitably it's hoodie season, so it's football season, though I mean the Bills got their asses kicked. I don't know if you saw the Sunday night preseason game in Chicago 38 to zero. A lot of it's a lot of bad, a lot of bad things happened in that game. So all you Bears fans, good job. Caleb Williams looks good. Bill's starting offense didn't really play, so there's not a whole lot really to say there, but our defense just has a lot to work on.

Speaker 2: 2:36

It's always like it's so hard to garner anything from preseason. Because it's like, if they do well, it's like okay, well, who are they doing well? Against preseason. Because it's like, if they do well, it's like, okay, well, who are they doing well against? It's probably not the first team. And then if they do poorly, it's like okay, like, did they really do poorly or are they just not playing the same plays that they might play in the in the actual season? And it's just. I mean, it really is practice. Yeah, like it's good to see people going through routines and stuff and you can, I'm sure, garner some insight, but for the most part, the score to me is absolutely irrelevant yeah, yeah, for sure, for sure.

Speaker 1: 3:08

You can kind of treat each drive and almost each play at some points as individual and exactly like they like that's where you learn something.

Speaker 1: 3:16

Yeah, like you know, you got like a fourth. I think the one play was like fourth and eight and it's like in a real game, they never would have would have gone from it Like, all right, you know it's preseason, let's, let's practice this and kind of see how the coaches react and how the players react and all that stuff. Um, I would have liked to see like some points on the board, but we just stopped watching it. So, um, hard knocks, though. Another episode dropped this week. It's just getting me ready for the season, man. So one more week of preseason and then, yeah, we got to. I believe it's a. Is it a week off? And then, yeah, week off, and then the regular season, if I got that. Yeah, yes, correct, because Labor Day weekend, and then get into the season the following weekend.

Speaker 2: 3:58

US Open kicked off this week. Tennis.

Speaker 1: 4:01

Oh yeah, so I'm not a big tennis guy, but what's the big rundown on it? That's one of the big four, right?

Speaker 2: 4:07

Yeah, it's two. It's like the four majors, I think. In the order it goes Australian, the French Open, then Wimbledon, then the US Open. I mean it's only the first two or three days in. So like, basically it's a bunch of qualifiers. I mean I kind of have it on the background. I mean it's nuts Even watching the qualifiers with unranked players, dude, they're so good Like just watching them and practicing and playing more tennis this year, like I can tell just how much better they are than just watching regular. I mean it's just night and day.

Speaker 1: 4:40

So side note on tennis I was away for Army late last week and throughout the weekend down in Pennsylvania we had we went out for like dinner the one night at like a local, like restaurant right off the base. They had like it was like quiz night basically, and one of the questions I had no idea I learned this about tennis Did you know that? The question was like the Davis Cup, which sport is it like the premier or whatever for. The question was like the davis cup, which sport is it like the premiere, whatever for? And I was like it's definitely not. It was like was it tennis, badminton or something else? And I was like badminton, I guess they're like nope, it's tennis. And I was like I've never heard of the davis cup before. That's like the premier international, like event or whatever.

Speaker 2: 5:20

I don't know here's the cool thing about that. I just learned this too. On like Monday they were talking and doing interviews about the Davis cup the Davis cups right up the street. It's in Delray beach. So next month I'm going to take Ava, because it's literally like I literally ride my bike up to where the tennis center is. It's a huge tennis center right up the street from us. It's in the middle of September and I mean like I'm super excited. Tickets are only like 50 bucks. So like I'm definitely going to take Ava and my wife up next month to go to it. Didn't know about it at all, didn't know? I mean, I've heard of it, but like I had no idea. To your point.

Speaker 1: 5:51

Everyone knows. Like the big ones, you know what I mean. Like Wimbledon, was it the? What are the open? The french open wimbledon, and then us open, us open, okay, french open. I didn't realize there was a french show. It's the clay court one. Oh, that's right. That's right, um, so that's sports news. Uh, it's hurricane season. Right, this is something we talk about literally every year. Yeah, and because it does impact freight on a micro level, if, um, well, it's usually when, when there's a storm that directly impacts the us. So, like this first one, is it, I think, hurricane erin? Um, not a direct landfall, it's the first, um, I believe it's the first hurricane to like. Actually, is it the first actual hurricane of the season? Does that sound right?

Speaker 2: 6:42

yeah, there's probably been named ones because they start at a yeah, but they'll start like as a tropical storm.

Speaker 1: 6:48

I think it's the first one that actually turned into like a.

Speaker 2: 6:50

Either way, we're early, it's august, so we're early into uh in hurricane hurricane season starts in june, by the way, like they start talking about on the news in june, but like I have never even seen a hurricane warning. I've lived here for 10, 11 years, until late September.

Speaker 1: 7:05

October.

Speaker 2: 7:06

And pretty much. It's basically like six weeks, like middle of September to like end of October, when the ocean, I guess, is warm enough that they start making landfall.

Speaker 1: 7:15

Yep, yeah, I remember it's wild. I think back to like Hurricane Sandy, superstorm Sandy back in 2011 or 12, 12, maybe, um, the national, so that one impact, that one hit like New York City and the National Guard, like we all got involuntarily activated like for a month, and that was October. Because I remember, um, I remember after the storm hit, it snowed like three days later and I was like this is the, this is like October in New York. You literally never know what you're going to get. We just had a hurricane come in and flood New York City and rip up Staten Island and then it snows like just insane, but yeah, but anyway a big takeaway when you've got these storms Insane, but yeah, but anyway a big takeaway.

Speaker 1: 8:11

When you've got these storms, I'm telling you guys, if you do any kind of female work or you've got business that's in or out or affected by, those are historically the areas that get either direct impacts or residual effects and it's going to disrupt the market for like a week or more, depending on you know how severe and the size and all this stuff. So you'll see on a micro level, like trucks just get out of Dodge, nothing happens for a few days. The storm clears and then boom, there's this huge demand and it could just be standard freight business or it could be FEMA. It could be FEMA pre staging things beforehand. Right, you've got there's like a bunch of different areas throughout the states that are like staging areas for like basic supplies like water and MREs, those meals and generation, power generators and power infrastructure, things like that. So keep an eye on that. And then don't forget, like some of these storms have residual weather effects that push all the way north for, like you know, four to seven days afterwards, so you'll have lesser impacts in those areas. So this is kind of like your precursor to like winter weather, um, but in the tail end of summer.

Speaker 1: 9:29

So happens every year. We talk about it every year. Don't be surprised when that first hurricane disrupts your, your customer's business, because we know every single year when hurricane season is. So that's my, uh, my news, um, oh, dude, other big news thing and this was actually down in your area and, well, my parents, town of fort pierce, that is the uh, yeah, so the we had it in our newsletter this week and it's, it's all over, it's on, like you know, it's national news right, the the carrier that um illegal u-turn on the Florida Turnpike. I don't know what's your. I guess what are you hearing on a local level Cause it's down in your area and then I'll give him. I'll give you my spin on it, cause I had. I had a long discussion about it with someone yesterday.

Speaker 2: 10:13

I didn't really. I mean, there hasn't been like like there's not much more coverage than what happened. The guy made an illegal U-turn and killed three people and didn't look like he gave a shit at all, like the guy sitting next to him is eating potato chips and he makes an illegal U-turn and kills three people.

Speaker 1: 10:30

Well then, you find out, he's not even legally in the United States.

Speaker 2: 10:34

Oh, didn't see that.

Speaker 1: 10:35

Yeah, so he's an illegal. The guy was, I want to say like three years ago he had a and I could be terribly wrong here, I might be misquoting this, but I believe something happened like three years ago that he had like a warrant to be deported or whatever, but he was. So he's either way not legally in the United States, but he was somehow issued a CDL from the state of California. So this is this big question now. Like one of my guys called me yesterday and was like he's like I could have loaded that guy like all day long. He's like how do I know to check for like legality?

Speaker 1: 11:10

on the driver level Because he's worried about broker liability. You can't even get to that.

Speaker 2: 11:15

You have to pay for that In order to get that information, you have to pay, and I don't even think you can get it as a broker because, like we tried, I think, last year, and dug into that to see what was available, and like you pay for it, and I think you need to have like an asset MC and you're paying for like employment records and it has to do with like restrictions around getting records for like hiring and I genuinely don't know. I don't know it's not HIPAA, but like it's for sure wasn't, and it was like 20, 25 bucks, I think, per record and you had to wait like a few weeks. It's not something that's readily accessible, if I remember.

Speaker 1: 11:50

Yeah, so here's I'm reading this directly off of. This is actually the the Times of India, because he's a. His name is Harjinder Singh, indian immigrant trucker. It says he flunked the English proficiency and road signs test after the crash. He only answered two out of the 12 questions correctly. So this is that big, you know.

Speaker 1: 12:12

So it was one of those like emergency only, basically what police use to turn. So you know he pulls off to the right side of the road and then tries to do a U-turn through that median onto the other side of the turnpike and there are signs there that tell you you can't do that.

Speaker 2: 12:30

I've seen this. I mean I've driven up and down that road many times, like I know exactly.

Speaker 1: 12:34

Right. And then they give him the proficiency test and he got two out of 12 questions correct. So that's where I think the big proficiency thing comes into play, and, um, but either way.

Speaker 2: 12:46

I mean it's kind of common sense, like English or not. It's a giant sign that has a big red, a big black upside down you with like red lines through it. It's not like you have to read it, like you just have to see it. I mean, my daughter, who's six, would be like yeah, don't turn around, right, dad.

Speaker 1: 13:02

Exactly, exactly. So that brings up the big question of like. You know, when I, when I've got one of my guys call me like dude, like I'm vetting these carriers out and I'm making sure that they're they've got insurance, that they've got the authority that they've got, you know, I'm looking at safety stats, he's like, but I can't see driver level data. I don't know if this guy, like he's like what am I supposed to do, ask him for to prove his citizenship. And I was like, oh my God, it's a great question. I said I'll definitely bring it up in our discussions on on the Hill and DC in a few weeks, but we don't have access readily available to that. Nobody does drivers on a driver level basis. Like, yeah, we can ask for a driver's license. You know if a customer requires it for checking license. You know if a customer requires it for checking, but like he has, he has, he's got a CDL right, but he's.

Speaker 2: 13:50

But he's not, but he's government and the state allowed to be driving. So it's super weird. And somebody told me like you don't even need like documentation to get like a regular driver's license, like you can just get one without like proving that you are like your citizenship. And apparently it's the same with CDLs. And it's also not straightforward either. Like my wife immigrated here in like 98. And like occasionally we've had to send documents like her green card.

Speaker 2: 14:13

I don't even know what it is, but there are like four or five different categories, if I remember it's like naturalized citizen green cards, working visas. It's not like a black or white system either where it's just like oh hey, you have this document or you don't. There's like four or five different categories you could be under. Like it is not even if you have the information to like somebody that doesn't do that or isn't in that side of things. Like it is really hard to understand what and where somebody is qualified to do whatever work in any industry, let alone this, and it's just like. The part that kills me is like it absolutely are these government agencies that aren't doing their job, in a sense of just not vetting, not checking these things, giving people licenses and allowing people to operate these things and then it's like, ok, well it's, we're legally liable for not checking what we can't check with information we don't have, because the government is inept and can't seem to get their arms around verifying and vetting the businesses and the people driving this equipment on public highways.

Speaker 1: 15:18

It's absurd, see. I think if you fast forward three years from now, I bet you're going to start to see some level of driver level data, whether it's minuscule or you know, or more detail. But I believe our vetting software is, in general, is is aiming to get to that point where, like I know Quickscope, their newest version that they're going to release their goal is to get to driver level data where you can see not just how the carrier performs but an individual driver, so like a driver scorecard and things like that. So and I I would be willing to bet that other, um, you know, other carriers or other platforms and services are probably going to aim to do something similar. So because when you try to take everyone, like if you go to a carrier that's got 10,000, like Landstar, like 10,000 drivers or whatever it is right and like yeah, the MC looks good, but like how do I know how one guy or gal is going to perform versus somebody?

Speaker 2: 16:13

else, now throw in leased in drivers and you got leased on drivers. I mean, there's so many caveats that make that almost impossible to do from like not the consumer side, but like the business side of things. I mean, I guess like the public side, not the government side, like you just literally don't have the information and there isn't any straight line between Let me see if I can find this.

Speaker 1: 16:35

I had two instances this week that I want to share because these are let's see if I can find it Basically two fraud things that were caught. Uh, okay, yeah, so, um, we want. These are two of our, of our brokers in our company. So one of them was was talking to a quote-unquote dispatcher, um, whose phone number was not an approved phone number in highway and even though the carrier passed all of our rules in highway and everything, um, this the girl. She ended up calling that carrier and saying, hey, I'm talking to so-and-so who's saying they're from your company and um saying that they're a dispatcher for you and like the carrier's like no, we don't know who that is. So, like the, the stolen identity and like, basically, this carrier, like no one had flagged them yet for a stolen identity, otherwise we would have known like, yeah, they're going to fail our rules, not that we can't use them, but if we would have saw, hey, victim of identity theft, we're going to verify the name and phone number, who we're talking to, whereas this one hadn't been flagged yet, no one reported it and we might've been, you know, the first attempted victim of a stolen load, right, so that was one. So make sure, gave you know, gave MC number and everything, and showed up.

Speaker 1: 17:52

I think it was. It was either. I think it was quick scope that caught it. Like they went and got there, they did their picture at pickup and like the MC didn't match up and it failed verification, so like we were able to catch it right there and it's like you know. Then they try and say, oh yeah, like I'm leased on, it's like you're not leased on because that you know your lease agreement and you're not leased on because that you know your lease agreement and your. First of all, if you're leased on and representing a certain company, you need to have their MC on the side of their truck. Yes, right, so it was basically two attempts at stolen freight and fraud. So keep your eyes out for that kind of stuff.

Speaker 1: 18:27

The only way in a soft freight market, the only way that scammers are able to make money is by theft, whereas, like you go back four years ago, they could just rebroker freight and make a little bit. They'd skim off the top and, like you know, do that in volume and make money. And now it's like, well, there's not enough money in the business, now. There's not a freight flowing right now that they just have to steal stuff. So wild, yeah, crazy man. Did you see the video? I think it was. Uh, I think it was jason miller on with ken ademo, maybe leffler talking about watched it live.

Speaker 1: 19:00

I was actually talking with those three yeah and they're talking about like freight rates, and jason miller was like, sorry to like break the news to you. He's like, but basically we're not going to see any movement until late 2026 and I was like, oh my god, that's like a four year trucking recession, absolutely wild. We don't know what's going to happen. There's just nothing, is nothing externally is moving the needle like far enough to to jolt you know, jolt us out in the other direction.

Speaker 2: 19:27

Yeah, tariffs are putting more and more pressure downward pressure on consumers and the volume of goods being shipped, and they're slowing down. It's not speeding the economy up, it's doing the opposite. As we were about to pull out of the freight recession, the tariffs basically threw a big wet blanket on the market, and we're still trying to peek out from underneath it.

Speaker 1: 20:38

Yeah, Yep, all right. Well, what can we talk about today? Ben, this was your idea.

Speaker 2: 20:43

Talk about sales. We haven't talked about that in a while and, just like I think, expectations, how to approach calls, fundamentals or basics, but like they always work.

Speaker 1: 20:52

Like your value proposition, almost, or kind of. What's the angle on it?

Speaker 2: 20:56

No, even more basic, right, like I always try to go down to like what is like the root cause of anything. Like as simple as you can explain it. If you ask enough questions, you can get down to like the fundamentals of like anything. Right, most people try to solve problems from like the symptoms, or like one or two steps removed, meaning, like what do I say? What is the perfect way to talk to somebody? How did I speak in a way that makes them want to buy the thing I say? What is the perfect way to talk to somebody? How did I speak in a way that makes them want to buy the thing I have? Like that is so far down from like how you actually connect with people that like yeah, you'll get a few more, but like that doesn't really help you get or improve at it. Right, and I'll give you an example. Like I'm going to take an analogy of golf, right, cause you play quite a bit of golf and like I think about them very similar Tennis, golf, baseball, basketball anything you're trying to do physically is very similar to what you're trying to do with your voice and a phone or trying to do in sales, right? So, like in golf, people will go. You're slicing the ball. Just change your grip a little bit, okay, maybe you will slice a little less. You're still going to slice because, fundamentally, the problem isn't in your hands. It's probably how you're standing, how you're actually mechanically bringing the club back and how you're swinging it Right, not the very last piece where the club head meets the ball, it's all the way up through your body, how you're standing, your posture and doing that consistently. That's why someone hits a good ball and then a terrible ball, because they're not paying attention to that. Their shoulders are leaning over. The next time, their feet aren't in the same place and if you have a pendulum on a triangle and you move the triangle, the pendulum moves underneath it Like that's all. A golf swing is right. You got to go all the way down to like the fundamentals of like how you start shooting a free throw. It's not just how the ball leaves your hand, it's where your arms are, how you're standing and the way you, your mechanics, are. That's why, fundamentally with little kids, that's what they teach them, right. Even running, you can run incorrectly and inefficiently and you can run efficiently and correctly. It has to do with how you're running, not how fast. You start there and then you improve from there, right? Weightlifters talk about the same things, like if you want to get better at that. Like you start fundamentally lifting like literally no weights until you get good at the movement and then you increase your weight. You don't do it incorrectly and just keep putting more weight on. You just break things and things fall apart. Right.

Speaker 2: 23:15

Well, in sales, right, like, fundamentally, the objective is to just get people to know you, like you and trust you. Right, like that's who people do business with in any scenario, right? So when people are thinking about like, how do I sell A sale is the result, and we always talk and kind of joke like it shouldn't be called sales, it should be called shins. And you occasionally get a sale because, like, statistically, out of a hundred attempts you get one or two sales, 98 are rejections. Right, and the goal is how do I get less rejections and more sales? But that's the result. Right, and we normally talk about like the simplest way to solve this is to just make more calls. Because, well, if I make 500 calls and you make 200 and we each get two out of 100, I get more than you. Okay, that is true, but if you go all the way back and you think of like who are really effective at sales and like this is one of those cliches is like God gave you two ears and one mouth, use them proportionately In sales, you should be listening more than you're talking, right?

Speaker 2: 24:15

So go all the way back to the fundamentals and think about anybody you've ever connected with that you actually enjoy talking to. Does that person talk 90% of the time, or do you talk more and that person listens? Most of the people you enjoy spending time with at least listen as much or probably more than you're talking, and that's why you enjoy spending time with them. The same way they always say is like, the sweetest sound to everyone's ears is their own name, right? Like people like to talk about the things they're interested in, and if you're listening, that person's happy. They're connecting with you and sales is far more about listening than it is ever talking, right?

Speaker 2: 24:49

But no one ever wants to talk about that because they're like oh well, what do I need to say to get them to say, yes, it's actually counterintuitive. It's like how do I listen more and just ask a few questions to keep that person talking. That's how two people actually connect. And also, by the way, like that's how communication happens, you aren't learning shit if you're talking, if you're listening, you learn lots of things about the other person, their business, what they need and what they don't need, and that is closer to the fundamentals of what most people aren't doing, especially early on in sales. That they miss and it's mostly because their ego's, in the way they're nervous, they're scared, they're worried about a result, so they're just talking and talking and talking and like I'll get on sales calls with even people on our team, or like like clients and I'm like if you listen to that call, I'm like who talked the most? They're like why did I'm like you talk or a lecture?

Speaker 1: 25:43

I guess it sounds like a lecture. I want to hop in here because this it brings up two. I'll give you a freight related one and a generic sales example from the past. When you go into a sales conversation, it's good to have to have general understanding of what the case might be for a customer, but not to have a predisposed assumption that those things are true. So, and what I mean by that is, let's say you're targeting a customer in Florida and it's during hurricane.

Speaker 1: 26:14

Let's say, no, I'm not going to use hurricane, we'll just say we'll talk about, like produce season, you know, don't go in and assume, like you might assume, based on the time of year, there's an impact from, you know, harvesting and availability of certain equipment types and yada, yada, yada. If you go in with that assumption and never ask and just have your conversation with that assumption and you're wrong, the conversation is going to go, it's going to fall on its face, right, because it's, you know, the same thing, like you might assume right now that a customer is having, you know, not a whole lot of issues getting equipment, or you know, trucks, because of where the market's at on a macro level and that they're just price sensitive right now. Blah, blah, blah and you talk to that customer and you're trying to sell on price and that customer is like I don't want the cheapest truck.

Speaker 1: 27:03

My issue here is like if I don't get this delivered on time and with great service, I'm going to lose my customer. The same thing. I remember this happening when I worked at Best Buy. I've given a couple of examples of my my college years. But like I remember back to school season literally right now people are going to going to college or back back to high school or whatever, and a lot of people are buying laptops. And I remember like at the time, um, every brand came out with like their cheap level, like hey, it's got four gigs of Ram, it's got two, 56 gigabytes of hard drive space, dual core processor. That was like the standard, you know, if you go back 15 or 20 years, whatever it was. And we had this one sales guy. He was like, he was like terrible, but he was even his best buy. So like it's not, like we're, we're selling like massive uh ticket items here. But this is a guy like argue with customers and tell them what they needed. So I remember this one.

Speaker 1: 27:59

This one person comes up and it was like august and he just assumes, based on the age of the guy that was trying to buy a computer, that he was a student going back to school and he's like trying so hard and the guy keeps asking to look at other computers and he keeps trying to sell them like these, like the base model the best back to school computer.

Speaker 1: 28:18

And eventually, like the guy comes over to me and he's like dude, I'm just trying to buy a gaming computer and this, this dude, keeps trying to push me on whatever, and I'm like, all right. So I'm like, well, hey, let's, let's talk about what games are you playing. We can actually look up and see what the requirements are and then recommended specs, and then we can show you some of the options that are out there. And it was just that little, slight difference of like listening.

Speaker 1: 28:37

Not everybody everybody's in the same situation at the same time, just because of what's happening. Yeah.

Speaker 2: 28:42

And listen, don't make assumptions. Right, Making an ass out of you and me, right.

Speaker 1: 28:46

And if you listen, you understand where, or if you can actually help that person, right, yeah, so I think if you go into all these conversations as almost like a curious little investigator, right, I want to learn, like, first of all, I want to show that I'm curious and my interest has peaked about your industry, cause if I'm, if I can get you talking about what you do every day, you're going to enjoy talking about it and I'm going to be able to learn a ton about your business and I'm going to start to uncover certain things. I'm not going to go in and say, hey, yeah, I know you guys are all price sensitive right now and trucks are easy to get and blah, blah, blah. It's like, well, that may not be the case right now. So I, you know that was a long winded interjection there. Not at all, it was 100% super relevant.

Speaker 2: 29:26

Right, because like and I'm going to go on a tangent and then I'm going to bring it back in a second, because this is what made me think about this and how I got to this point. Right, which was, I remember, when I first got married right, and like it a kid, and your life is very different, and like you are trying to connect with that person so both of you can understand each other and cooperate. Right, like just basics. Right Of two people living together. You don't need to go down like the avenues and like what that all means, but it's like OK, like fundamentally, that's what two married people are trying to do is to go from living by yourself to working as a team, living together in a way that both people are happy.

Speaker 2: 30:02

Right, and at this time, I'm reading all these consulting, coaching books. I am going in deep dives into psychology, how the brain works, and honestly, a lot of it was like manipulation, like how you can literally use techniques that are used in, like the intelligence industry, the FBI interrogations to literally manipulate people, how to read what they're doing and how to use subtle cues to get them to do what you want, and I thought that was sales until I was probably 35. So that's where I spent most of my time and energy and you kind of realize that, like one, it's exhausting to do, that it takes so much focus and concentration to be paying attention to these minute things to execute that. That one, it's not enjoyable. And two, even when it works, you kind of feel like shitty about yourself in a way, because you know that like you basically created that outcome.

Speaker 2: 32:08

In a way that, and also what I also noticed in like other types of sales I would do is you would lose a certain percent of them for buyer's remorse. Like I could get people to say yes over and over in transactional sales, but like the next day or two when they thought about it, they realized like they didn't really want that anyway and they would cancel. Right, and you have this problem of like you get more but people are going to have buyer's remorse and they cancel. And it's because, like you're literally spiking their emotion, getting them to the buying line and getting them and closing them right there by getting them to give you the closing details, signing your agreement or whatever it is, and then they think about it and realize like oh, that was just like an impulse buy and you get really good at getting people to buy things impulsively.

Speaker 1: 32:46

So so I think back to like well, continue, and I'll hop back in. I'm going to take it back to my my Conway Freight days and how we sold there.

Speaker 2: 32:56

So, as I got married and then, like I remember this very vividly, like where they would be like I don't even want to say like an argument, but it was really more just misunderstanding, where both of us had the same objective but we weren't really understanding where either person was coming through. And I remember literally playing conversations back in my head, just like I would do at work, right, because that's where I spent most of my time, listening to sales calls and listening for these cues. And I'm like I know I said that in this way and I know when she said this, I responded this way. I repeated back her what she said so that she felt heard, I said it in this way. And I'm like focusing on the semantics of language and I'm like I don't understand why we're still upset with each other when I feel like I did exactly what I've learned how to do in sales but at marriage, like it just kind of didn't work and I'm like I don't know what I'm missing. And I remember digging into that question because this is a years long process and like talking with, like I think it was like my coach at the time or whatever, and I'm like I feel like I'm not connecting with her emotions, but I'm connecting with the logic, right, and the more I thought about it, I'm like, oh, that's the surface area, the words, but where she's coming from is like I'm not connecting with how she feels about the situation. And then I at first went like, well, why can't this other person just put into words what they're feeling better? And I'm like, well, if you go back to it, like you can't make anybody do anything differently, you can't train somebody else to speak in a different way. Like you have to change yourself to be able to communicate better.

Speaker 2: 34:27

And I'm like what I really need to do is to be able to learn how to communicate and understand or actually, more simply put, feel what this person means, not just what they're saying. Right, what is the meaning underneath the words? Right, and this is where, like it sounds like I don't know, like a theory or whatever, but like I kind of started digging into meditation because, like all meditation really is, the more I started reading about it, it's like you practice being quiet with yourself and just being aware of what your own brain or ego is telling you all day. The crazy noises like the thoughts, the racing worries, the anxiety about a load picking up. I got to call this person back, I got to do my laundry. That racingness, that is actually what is preventing you from feeling what the other person means. And it doesn't mean just in like a relationship, like literally in a business context, like just being open enough to hear what you mean when you're talking to me about even logistics. I can't hear that shit. If my brain is literally drowning you out, then I'm just waiting to speak.

Speaker 2: 35:28

And that's what they say in communication is like you can either communicate by listening and then responding, or waiting until you're done talking to say what I'm already going to say, or I'm already thinking about what I'm going to tell you while you're talking. And I didn't hear anything. You said Right.

Speaker 2: 35:43

And I noticed that like the more you practice that, like even if it's five minutes a day, to just be quiet and just be aware of what your brain is telling you and just going, oh OK, that's a worry, and you just start to identify them, that stuff. It's like turning the volume down in your own brain. And the more you practice that, the more I was able to like be aware of what other people meant, not just what they said, and like the more I practiced it, like I started to notice, like I got way better at sales. And it wasn't closing deals, it was just that if I talked to 10 people and normally I could connect with one or two out of 10, I can connect with five or six now because, like I'm not in my own way and I'm not preventing myself from hearing what that person is saying and it doesn't matter what they're talking about.

Speaker 2: 36:29

Like it could be the mailman, it could be a business call. But, like to me, like that is the root hurdle for most people in sales is they're so anxious and worried about their own fear about not selling, their need to sell more, they're worried about not having enough money, they're worried about not having a job, that all that worry is actually clouding their ability to just listen to the person they're calling, which is the root problem of why you're not selling more. You're just not connecting with enough people because you can't quiet your own shit down enough to hear what somebody means, not just what they say. Dude, I shit down enough to hear what somebody means, not just what they say.

Speaker 1: 37:01

Dude, I got so much to add here. So the one of the reasons we are all about repetitions and lots of calls, lots of conversations Think about how a large language model is built right. Think about how, yes, gpt Context Right. Like, the more conversations it had, the more it learned, the more it listened to feedback, and then you have these new models right sales people, freight brokers, right develop. In the same way that the more repetitions you put in, the more times you ask a question, the more questions you ask, the more answers you get, the more objections you get. You start to understand. That's why, like I can go into just about any conversation related to our industry right now and, without having to like think, I can, or you know, without having to like think hard, I can usually just navigate through the conversation because I've I've had thousands and thousands of them over years and that's why you know these. The repetitions help. So it's funny, one of the things you have are you familiar with the spin selling method? Have you heard of that one?

Speaker 2: 38:03

I've heard of it, but I'm not familiar I had to pull up the.

Speaker 1: 38:06

I had to kind of refresh my memory Cause this is this was like the what when I, when Conway freight was still around and I worked there, that was like the prescribed sales methodology and it really goes into what you were saying earlier. So it's it's situation, problem implication and needs payoffs for like basically it's a lot of asking questions right and hearing responses. So it's that active listening, that whole God gave you two ears and one mouth that you talked about earlier and really trying to understand and get into the mindset and the shoes of the customer. So situation is, and it's it's funny because we, like a lot of the examples that I pulled up here for freight brokering and for freight broker sales are things that you and I have said for years. So, like situational questions, it helps you understand the customer situation. So things like you know what's a typical lead time for one of your shipments, what lanes are you running on a regular basis, do you have a set of group carriers or brokers that you work with, or you know how do things look spot versus contract. You're trying to just understand. We're not even proposing anything right now. We're just trying to learn, qualify, understand the situation of that customer and then it moves into some of the P is problem. So now that I understand situation, let's say it's lead time and they say, oh, lead time is we usually only have like a day, right. And then you can go into problem questions like well, what happens if you don't get that load covered in that lead time? Right? You start to figure out what are some of the problems, like have you ever had a truck not show up on time? Have you ever had a carrier that picked up on time but you couldn't track them and give accurate updates to to the receiver? You know, but you couldn't track them and give accurate updates to the receiver. You know. If it's pricing related, you know, have you guys ever run into issues with rates spiking at certain times of the year and it throws your budget off? Right, these are problems.

Speaker 1: 39:49

Implications is what happens if a driver doesn't show up on time? What happens if you end up paying more than you had? Right, you know what happened. Or you know paying more than you had right, yep, um, you know what happened or how you know. Anyway, those are your implications. Then your needs.

Speaker 1: 40:04

Pay off is where you you eventually get the the customer to suggest the solution. Right, like, yeah, you know what, um, we really should try to be doing x, y and z differently. Like, yeah, it's a lot of times like that whole process doesn't happen in one conversation. Right, your first conversation with, like, a customer it might be the fifth time you try calling them, it might be the 12th time, it might be the 20th time, but you might just be talking about situational things, right? Hey, yeah, I got five minutes. What's going on? And you start learning about volume of hey throughout the year. You know October to December is their busiest time, right, they're fairly dead during the summer. They might move one or two truckloads a week in the summer, but they're up to like 12 to 15 a day when we get to those fall months into the wintertime. Right, you start to just understand what size you know. You're starting to just qualify them, right, do you? You know? Do you know what they're moving?

Speaker 2: 41:00

Is there a need that could be solved? Yeah, Exactly. All qualifying means is did you uncover or did they tell you about something that you could help with? That's all qualifying is right Exactly.

Speaker 1: 41:12

And the more conversations you have, the more trust, the more rapport, the more familiarity you start to develop with these folks. Then you get into more of those problem and implication questions. You know I'm not saying the spin method is the way to do it. It's just how I learned freight sales. But any effective sales methodology all kind of revolves around the same thing of like. You need to understand your customer and be able to properly offer some sort of value. Most people don't get there.

Speaker 2: 41:41

Yeah, and most people don't get to the understand part. The solutions are easy. When somebody is telling you what is wrong, the solutions kind of come up by themselves. Like you don't need to be a genius that when somebody says my loads aren't picking up on time to get to the need and then to figure out, okay, well, the solution is like all right. Well, how quickly are you tendering your loads? You send them out an hour before they need picked up two days. How much are you paying? Do you think it's because you're paying carriers that are trying to like really run from their last delivery to your pickup in a short amount of time? Like it really is kind of just a logical conclusion. You don't have to put a ton of thought in there.

Speaker 2: 42:20

But like, where I think most people have the difficulty is getting to the understand part, like getting somebody to talk to them and it's because, again, like they're not one, I don't think most people are present when they do this, I don't think they're making phone calls. And again, like to take something from like the like Buddhism side of things, like they're not being mindful. All mindful means is, when you're doing something, only do that thing and pay attention to that thing. So, like, if you're making cold calls while you're scrolling through whatever social media or while you're reading emails, when someone picks up the phone, you probably aren't present there at all, so what is the likelihood that that person is going to actually connect and talk to you? It's about zero, right, if you aren't there. And again, like, you don't need to have some presentation planned, just a hey was trying to catch up with you, have some idea of what you're going to say before it, know who you're calling and when the phone picks up, just do that thing. I know it's hard in freight brokerage, because there's always 10 other things you need to do. Everything's always a priority brokerage, because there's always 10 other things you need to do, everything's always a priority.

Speaker 2: 43:29

But, like, if you can practice just that alone, I think you will see far more of your calls turn into actual leads. And if you get more leads, more prospects, it eventually will turn into more business. Right, but instead of just figuring out, oh, how do I close more of the people I'm talking to? Well, if you haven't connected with any of the people you've been talking to, you can't close shit. You're not going to close any of them because, like you haven't heard them, they haven't connected with you.

Speaker 2: 43:47

Neither one of you are paying attention. When you're on the phone, the person you called is busy doing whatever they're doing. They're barely paying attention to you and you're not paying attention to them. How well of a conversation do you think is going to go if two people meet each other in any setting and both are staring at their phones while they're trying to talk to each other? How much communication and connection do you think happens? That's literally what's happening. You're staring at your computer, barely paying attention to the phone, and the person you called is doing the same thing, and you're wondering why you guys can't connect and do business together. It's because nobody's making an effort to actually be present in the conversation, which was the whole objective of making the phone call in the first place.

Speaker 1: 44:23

Yeah, yeah, I feel like we could do an entire episode on like active listening, right Like dude.

Speaker 2: 44:27

There's a great book on it. Dude, hold on. Just on that point. Somebody said this the other day. It made me laugh so hard. There's a book. I'll have to look it up. It's really good. The whole book is on listening. And somebody was saying like there were two TED talks One was like how to convince people to do what you needed to do and the other one was how to listen better. And the person and the Ted talk on how to convince people had like 10 million views and the one on how to listen better had like a hundred thousand. Like just nobody wants to learn how to listen, they just want to take control and make the thing happen that they want to, and like that's so true, I think.

Speaker 1: 45:05

So there's a guy Andrew Bustamante is his name. He's a podcaster now he's an ex-CIA guy. He was on Lex Friedman a few years back. That's where I first heard of this guy. But he's got, and other people like him have excellent discussions on like how to build rapport and how to how to like get a conversation to go a certain way, and one of the things that he always preaches is like the two questions fall by one validating statement and it's a form of like active listening, Like you ask two questions, they answer and then you basically give a validating response after those two questions.

Speaker 1: 45:43

That shows that you heard and understood what they were saying to you, right, yeah, and that helps build trust, because then the person that you're talking to feels like, yeah, he, he or she actually like heard what I was saying, they understand me. And oftentimes, like when a broker calls someone, it's just like I got trucks in the area, like, all right, cool, you're telling me what you have. You don't care about what's going on, what I need.

Speaker 2: 46:07

That book is called the Lost Art of Listening by Michael P Nichols PhD. Well, the other book we've talked about over the years is like Super Communicators, and there's a really good story in Super Communicators where they show this example where two people are arguing and at each other's throats, but they both have the same goal. They're just not listening to each other. And in the example it was a guns rights like Facebook group, I think. Basically it's a forum, right, and there's a group of people arguing that nobody should have guns and then there's guns rights activists arguing that people should have guns.

Speaker 2: 46:43

And when this professor got into this, they basically took a few of these people and brought them together, right, and they showed the technique you were talking about, about repeating back what you heard and saying what you think they meant right To be able to literally facilitate communication. And at the end of like 20 minutes they were friends and they both realized they had the same goal. It was safety. Both of them wanted safer communities with less shootings and less harm, and the guns rights activists wanted more gun safety, more training and more ways to protect people. The person who wanted to remove guns wanted the same goals. They both just had different suggestions for how to get to the goal.

Speaker 2: 47:20

And once they both listened to each other, they both realized, oh, we're on the same goals. They both just had different suggestions for how to get to the goal. And once they both listened to each other, they both realized, oh, we're on the same team. If we take some of your ideas and some of my ideas, we could actually work together to make the whole community safer. And they're like for years. We're just screaming at each other, thinking this other person is the worst person in the world, doesn't care about children, doesn't care about our community. But at the end of the day, both people literally had the same objective. They just weren't listening to each other and didn't take the time to get out of their own way to just hear what they're actually trying to achieve.

Speaker 1: 47:54

So excellent point, and it's that leads me into this. Next thought here is that when you have these conversations and we've talked about this stuff before like people are going to remember how you made them feel in those conversations. Right, and this is where, like it's a numbers game and repetitions and casting a wide net is going to come into play, because there are some people that you just won't, you're not going to connect with. It could be personality type, it could be age, it could be just the tone of your voice, it could be a lot of different things, things that you're interested in, and then there's people that you will click with, and, outside of just understanding them and their situation and understanding them, understanding what you can help solve for them, what can matter even more sometimes is do they feel like they are going to enjoy working with you? Do they feel like they can trust you? Do they feel like you're going to get the job done for them? And sometimes, like it doesn't matter if you know their problems and you can solve their problems If they just don't feel like, yeah, this guy feels like a good fit to work with. If they don't feel that it's not going to go anywhere right, unless you're like a last resort.

Speaker 1: 49:03

But that is where you know there's no one magic pill that you can take and say the right things and ask the right questions. It is like you got to do this hundreds and hundreds and hundreds of times with all these different people and companies out there and you will find the ones that you will click right and sometimes you'll find the ones that you click with well and they just don't have a lot of business and that's fine because you're going to have the little ones Right. But when they, when they've got that load every couple of weeks like dude, they're going to call you because they want, they trust you, they want to work with you, and that's how you build out your book of business and you round it out diversified. You've got some of all about, you know, ego you think you're right?

Speaker 2: 49:55

it is. Yeah, you're not listening.

Speaker 1: 49:57

You ever get the ones that like, uh, straight up, call you out.

Speaker 2: 50:00

And they're like yeah, yeah, I know, I know you're, you're going to make commission on this, blah, blah, blah, and it's like making the conversation so awkward here, but anyway, you know it also made me think of this the other day was like I've been playing tennis with older guys like 60 lives behind me in the mornings and he runs a painting contracting business and that's like probably 30, 40 years, right. But what I noticed as I was thinking more about this too and like again we could have like a two hour conversation on some of the other commonalities I've seen recently. But we're walking over to play tennis, right, and the guy is coming over to pressure wash, like the clubhouse and like the pool area, and he walks over and starts talking to the guy. You know pressure washing, it says hello, but it wasn't just the fact that he stopped to go over and talk to this guy. Like I could tell he was so present when he was talking to him that he genuinely cared what that guy had to say, how his morning was going and what was going on, right. It wasn't the just wave to give someone the impression that you care, like he was genuinely present while he's talking to this guy and I've seen him do this with a handful of people over the past couple of weeks that just happened to walk past, say hello, where he will literally stop what he's doing and just be there and hear them, and I'm just like this is why that guy runs a successful business, right. This is why he has a lot of clients and customers, because when he is talking to somebody, it doesn't matter who they are, what he's getting out of it, he is 100 percent paying attention and listening and hearing what that person has to say and what is important to them. He didn't have an agenda, he's just genuinely cares about connecting with people and like I'm like every single time I see him talk to somebody, he does this and I'm like it is second nature and to your point, like I know some people are probably better at that and it comes more natural.

Speaker 2: 51:50

Some people have to work at it, but I think everybody can get to that point because if you practice it enough and you get enough feedback which in our world is rejection right you verbally get punched in the face and someone hangs up on the phone on you or yells at you like well, I guess I didn't do that one right. But the best part is like you got another chance, pick up the phone and try again. It is like the only profession. You literally lose nothing except your ego gets a little kick and if you realize that, like that is just temporary and if you pick up and go at it again, you can just keep trying over and over and over and over and over and over again until you actually get better at it.

Speaker 2: 52:29

But if you don't know where you're going and why you're failing, that is very difficult. That's why most people go like I don't even know if I'm doing it right or wrong, like if people are talking to you and opening up, you're getting better at it. If you're getting less of that, you're moving in the wrong direction. Right, and it's mostly for the things we talked about. It's like you have an agenda. You're trying to convince somebody of something. They can feel that they know you don't care about what they need. That's why they don't want to talk to you anymore.

Speaker 1: 52:53

Yeah, I'll wrap it up with this, I forget her name. There's like some famous lady she had this quote or this like mindset shift and it totally applies to sales. It's change the go from why to what. So, basically when and I think about this when I've done cold calling sessions with with some of our brokers, after the call sometimes they're like man, why, why did that guy react that way? Or you know, why did he yell at me? Why did that? Why did I get hung up on?

Speaker 1: 53:22

Instead of asking the, why ask what, like what did I learn from that way? Or you know, why did he yell at me? Why did that? Why did I get hung up on? Instead of asking the, why ask what, like, what did I learn from that conversation? What can I, what can I take away from this and apply in my next phone call? Right, it takes a a potentially a negative thought and turns it into an opportunity. And I think that I mean we're not going to go into the psychology of sales too deep here, but that little shift and understand, like, like you just said, I have another chance, right.

Speaker 2: 53:45

Yes, so it's why you should. I think everybody should have a mirror above their telephone. One you can see how you look to yourself, what kind of mood you're in, what kind of energy you're bringing and whether or not you feel like you would want to talk to somebody making that facial expression. And two, like you said, if you get off the phone and you feel like why did that happen, the person you should be looking at to answer that question isn't to talk to that person to see why they did it. It's to look at yourself and ask yourself what you could do differently to maybe make that not happen again.

Speaker 2: 54:19

Because you can't control anybody else. You can control what you're going to do in your next interaction with whoever that person is, and that is the only way anybody gets better at anything. It's not blaming anybody else, blaming the situation, blaming the economy, blaming the environment, blaming your phone, blaming your leads. You can't change any of those things. You can change how you approach the next call and whether or not you're going to listen a little better and pay attention to how you're trying to connect with this person.

Speaker 1: 54:43

Absolutely man. Good, good discussion today. We got really covered a lot of ground there on sales, so hopefully you guys can take something away from it. Let us know what you think down in the comments. Ask us, you know, any questions related to it.

Speaker 2: 54:57

Final thoughts man, whether you believe you can or believe you can't, you're right.

Speaker 1: 55:02

And until next time go Bills.

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Freight 360
Freight 360

Freight 360 was born from a vision to share knowledge about transportation with everyone.

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