Why Most Freight Sales Reps Fail | Episode 301

Freight 360

July 3, 2025

Why do 95% of new sales reps wash out in their first year? This episode uncovers the mindset shifts, psychological hurdles, and authentic communication strategies that separate top freight brokers from those who struggle. Whether you’re building a sales team or trying to thrive in the industry yourself, you’ll get actionable insights to transform your results and boost retention.

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Show Transcript

See full episode transcriptTranscript is autogenerated by AI

Speaker 1: 0:19

All right, welcome back Episode 301 of the Freight 360 podcast. This is going to be a sales-focused episode today, so we know this is typically the majority of you really enjoy this kind of content, so hopefully this will be a good one for you. You've got the website. You've got YouTube, our Facebook group. Share us with your friends. Leave that review. I don't think we've asked for a podcast review in a while, so feel free and go over to Apple Podcasts or Spotify, wherever you're listening, and leave us a five-star review. Send us your questions. Check out the Freight Broker Basics course on the website as well, if you're looking for some educational options and what else here. Uh, subscribe. Yeah, ben. What's new man, besides your leaky roof?

Speaker 2: 1:11

yeah, do you know? What I was gonna tell you, though, is um, I found a couple new. I guess you call them like exercises, um, anyway, I went down. So, like the health and wellness guy.

Speaker 2: 1:25

I love it yeah, I was listening to this podcast. I can't remember the guy's name, um, but he was like, uh, he was on tim ferris and he was talking. He was a um, like world champion heavy lifter, but then he was also like a world champion in jujitsu or martial arts and the interesting conversation when he was just talking about was like how lots of traditional ways of strength training cause like immobility and like pain and then like damage or like injuries and stuff. Yeah, I don't know, I'm old. That's like my biggest thing now is like just avoiding getting hurt, because it takes like six months for anything to heal and to feel better.

Speaker 1: 2:06

Dude, you're telling I'm literally still like I'm just getting back into the gym, like I'm trying. I'm trying, like at this point now, to get back in after busting my knee up in May.

Speaker 2: 2:16

I want to say it was. That's why I was thinking about this, because I sent you that guy I think his name is Dr Baird, the guy who studies tendons, knees and really interesting Cause I sent you that guy I think his name's Dr Baird, the guy who studies tendons knees yeah, and really interesting Cause I mean like that's all he does and he just talks about like very little bit of resistance frequently helps strengthen them quicker. But this guy um, he was talking about this training. Have you ever heard of rope flow?

Speaker 1: 2:38

Yes, I never heard of it. It's like never heard. It's like where they. It's not like where you're doing this, it's where they're like literally spinning around.

Speaker 2: 2:46

Yeah, I've seen that. Think jump rope. Yes, you're not jumping over it, it's basically going around you or on either side and you find like a rhythm and it's less impact. But it's supposedly really good for like mobility and flexibility and spine and just working tendons and muscles, like the little ones you don't do very often specifically in strength training and things. And like I know it's because, like I told you this, like a couple of years ago I got like tennis elbow from lifting. I just like moved a bench or something wrong and it popped in my elbow. It took like a year for that thing to heal. So I was listening.

Speaker 2: 3:20

This guy was like they were talking about. He was like how quickly do you kind of see results or feel a difference? He's like this is the only exercise that like I feel better immediately after I do it. And he's like I've worked with athletes that see a difference like once or twice, like literally two, three minutes a day. After one or two days start to feel like you're a little more balanced, you feel you just feel better.

Speaker 2: 3:45

And I don't I used to swim and it's just too hard to get in the pool for that long anymore and I was like, oh, that's a really, and it seemed like kind of fun and easy to do. I started doing it like two weeks ago and both like one is it is actually very enjoyable. And two, I do it as like a warmup only for like a minute and a half or two minutes and like it really does, cause it like works everything. It like warms up your whole body. You've even I do it even before I stretch, cause it gets all the blood flowing and then when I go stretch I can do my stretches so much deeper. It takes like half the time to stretch. Now, when I do that first, cause I'm like all warmed up and I've got all the blood flowing through my muscles. Definitely worth checking out that.

Speaker 2: 4:23

And another guy I ordered these I think they're called the EMT clubs. This guy's named Weck, but that guy is the guy that I think invented rope flow and he does lots of rehab and he specifically has like a ton of strength training and flexibility stuff for golf and tennis, which are mostly what you and I do. So I ordered those two things last week and I've been doing them all week and like, to be honest, like, like it absolutely works. Like I've gone to physical therapists spent hours with them. It takes months and I see like nothing. I've done some of this stuff for like a week or two and I start to feel already a little less sore. I'm a little less sore when I wake up in the morning. I'm not as like achy. It was pretty significant actually for a very low effort.

Speaker 1: 5:05

Speaking of golf, I got to golf the kiowa ocean course last week. I know I sent you a picture from out there dude, it was sweet, expensive but really really cool for anyone that lives in charleston or has been there like awesome, beautiful areas, especially in the summertime it looked gorgeous. So, yeah, it was nice. Man, your towels in the mail, get your, add your collection there.

Speaker 2: 5:24

I use my Pinehurst towel regularly. The last one, nice.

Speaker 1: 5:28

Nice. What else is there in like sport? Oh, Wimbledon's on. It's actually on in my office right now.

Speaker 2: 5:34

Oh, dude, thank you for reminding me, so I'm super excited I don't.

Speaker 1: 5:48

I'm not a tennis guy but I like sports so I usually just throw on whatever's going on, so news, anything related. Sign up for our newsletter. We we push stuff all the time. I did see there was kind of a a decline in ocean shipping. Yeah, Kind of like a whiplash effect.

Speaker 2: 6:02

It seemed like not only that decrease there and like what everyone kind of expected. I saw this morning I was reading that like online sales have taken a double digit decline for the first time. I don't know, maybe it was ever. It's like basically everything we buy online. For sure, most part comes from another country.

Speaker 1: 6:20

And I was reading this morning Like the tariff pause is like coming up next week. Yeah, monday.

Speaker 2: 6:28

So Online shopping sees biggest slowdown in over a decade. Online purchases for home delivery experience double digit percentage. Year over year declines across major categories Office supplies down 13%. Sporting goods down 12,. Cosmetics, furniture, home furnishings, large electronics all fell by 10 percent. So yeah, I mean.

Speaker 1: 6:50

I feel like I'm my household's like been in the opposite direction. We've been buying so much crap lately, but I guess that's. I'm just one person. Sample size.

Speaker 2: 7:00

And it's just like I mean, everyone's like, oh, the stock market's rallying. And I'm like, yeah, most of the stock market rallies around like I think seven stocks. The other 500 or 493 are all barely kind of hanging on. I think the economy is absolutely not faring very well and I'm I mean the market's done well overall cautiously optimistic.

Speaker 2: 7:26

I'm hoping things get better, like, yeah, it just sucks not seeing any industries really doing well. I mean like it's anecdotal, but I'm like I don't know of anybody or any industries that are like actually doing very well.

Speaker 1: 7:39

Um, oh, news did you see the genlogs video.

Speaker 2: 7:43

No Dude, really cool. In fact, one of the carriers that is in there they did a video on anatomy of a cargo theft ring. It's on our free 360 page. You should, and everybody should, absolutely watch this because actually the first carrier in there was related to a theft with somebody I was working with and it was MTC Cargo. They stole a load out of California and how that actually went down and this is why it was really pretty interesting. So how this went down, was the criminal tried, didn't try, offered to buy a trucking company. The trucking company owner gave him the logins before he got paid, because the guy said oh, I want to go and look at all your logins and check everything before I send you the check for whatever 25 grand. And then that person was a criminal, changed all the logins, the phone numbers and the names and stole something like 10, 15 loads that day. But what was interesting was-.

Speaker 1: 8:45

I feel like I've heard similar stories before.

Speaker 2: 8:47

Yes and you have. But what was interesting about this one was they impersonated the carrier, meaning it was sophisticated. They had the magnets and everything done and the decals put on their trucks so that they visually looked like the MC that they were running under, even though they never actually bought it or owned it. Okay, stole somewhere between 10, 15 loads that day before everyone was kind of alerted as to what happened. The other interesting thing was Highway didn't pick up on the phone number or a few of these other things and they kind of got through. Now Highway later said that if you would have had LoadLock or their higher product, it should have caught it. But I don't know for sure if that was the case.

Speaker 1: 10:26

But here's where it gets even more interesting. So it flagged them for a recent change in FMCSA data, or no? It?

Speaker 2: 10:31

didn't flag anything because they never changed the FMCSA. They changed their phone numbers in Highway with the logins. They didn't change the FMCSA information. They changed the Highway information, gotcha.

Speaker 1: 10:44

Yeah, like their verified contacts or whatever.

Speaker 2: 10:46

Yes, and Highway said well, you know it's against our policy that the owner gave the logins to somebody else.

Speaker 1: 10:52

That's true. That's against their terms of service Right.

Speaker 2: 10:55

And I did ask them. I was like, well, don't you do MFA if somebody's logging in from a suspicious location or anything? And I guess at the time maybe they weren't or they are now, I don't really know.

Speaker 1: 11:05

I get it all the time. Whenever I log in from somewhere else, it's going to email me a code.

Speaker 2: 11:08

That's what I said.

Speaker 2: 11:09

I went to log in just a second and it's like give me your code If I put my VPN on it asks me all the time to do this, so, but here's what's interesting about the Genlogs video is they have VIN level data now, so they've been able to find that truck that was impersonating or that was involved in that theft, and I had the driver's license too, so I sent them the driver's license.

Speaker 2: 11:35

They not only found that VIN in that truck, but they found it in other thefts, so the same truck is popping up under all these different MCs to steal freight and gen logs can identify that specific power unit. And the whole video breaks down not only where they're also popping up, but that they're getting data ahead of these things to be able to predict it. And they've had shipper, I think photos or videos of the guy that was the driver in the driver's license that was involved in the theft that I was aware of, and it's a really great breakdown shows exactly how they're doing this, what was occurring, how they're finding them. It's really really good watch, interesting, I'll have to check it out.

Speaker 1: 12:12

Yeah, I just saw it's on our LinkedIn page. Very cool, all right. Well, anyway, today we're going to go through some sales stuff. So kind of the baseline topic here is why most people don't succeed in sales, and it was funny when I asked you this morning like hey, what do you think we should do for a topic, and you brought it up Literally earlier this week I was at my golf league and my partner couldn't make it, so he had a sub playing for him and it's another guy that I know, but we don't hang out as often, so we're kind of catching up and I was talking about work and he's like. He's like, let me ask you this he's like what's like the average freight broker make? Like what can a broker earn? And I was like what's like the average freight broker make?

Speaker 2: 12:57

Like what can a broker earn?

Speaker 1: 12:58

And I was like it really just depends, man. I was like. I was like I, you know, if you're fresh out of college and you go through like a training program at a big company and you do, okay, like you could make like maybe 60 grand around there and then grow from there. I said I literally have someone at my company that made a million dollars last year. I was like and that's your massive spectrum, like everything in the middle, it just depends on how well you, how good you are at it, how well you can scale it. He's like dude. He's like that's crazy. And I was like. I was like, yeah, I was like because he's like, he's like maybe I should do that. I was like.

Speaker 1: 13:32

I was like look, I said it's very high turnover. And I said it's very, very sales focused. I said people hear earning potential and in any sales, right, whether it's solar, freight, brokering, insurance, right. They hear that and they're like oh, I, just as long as I get a job in that industry, I'm going to kill it. And then the reality is like no, there is a lot that goes into this and I think we could definitely break down a lot of the reasons that folks don't succeed because we've talked about the numbers in the past, like TQL right, one out of 20, like is going to be there two years down the road after they start.

Speaker 2: 14:11

I think it's something like and this is, I think, with most of the large companies.

Speaker 1: 14:15

It's not even just T-Mail.

Speaker 2: 14:16

Yeah, like any of the big W-2 models If you stay in sales and you don't take like an operations role, which I think is different, and I'll explain what I mean. It's like if you just stayed in sales, like out of a hundred people I think, like 95 get washed out or leave in the first year. So there's like between probably four or five out of every hundred, maybe even a little less, three out of every hundred make it to like their first year and one or two stay beyond their second year. So it's like probably 4% make it through the first year and probably 2% the second year.

Speaker 2: 14:51

Now there's there's another category where folks like, really like logistics and are really good at booking trucks. They're really good at details, they like arranging freight, like the hustle and bustle of it, the fast pacedness. Those folks will typically take like a larger salary and lower commission to stay in the industry, but they get washed out of sales. Sales is the highest risk, highest return, highest failure rate. It's why the two highest paid positions in the whole economy are CEO and top salesperson in every company, almost Yep 100%.

Speaker 1: 15:26

So I think you make a good point there too. It's not just that they get fired, it's like hey You're actually probably better fit over here, and that's why there's different positions and different roles within a company. Because you might be like we're going to talk about why people don't succeed in sales. But you might be really good at sales, but you are terrible at organization and you know project management and things like that, where somebody might not be good at the actual sales part of it, but be really organized, really detail oriented and all of that stuff. So that's where you might.

Speaker 1: 16:01

That's where you see oftentimes you're you know, when done correctly right, your supervisor or your leadership is not necessarily your best salesperson. It's someone who's a really good leader and is, you know, good enough and understands sales and can do it. But they're not killing it in sales. They're really good at leading a team and leading an organization and having that long term vision. Same thing with, like carrier sales folks. They might be really good at talking with drivers and securing capacity, but you put them on the phone with the shipper. It's a very different conversation.

Speaker 1: 16:34

Very different job, yep, and same thing with an account rep, you know, versus a carrier sales rep. Very different job. I'm going to do the job and for that reason I'm going to get the income and be happy.

Speaker 2: 17:10

So I pause right there, because you know what I kept thinking of when we were going into this is there was a guy I met this is probably 20 years ago and same thing, sales, but he was in like financial advisory, right. So very similar type of failure rate, success rate, very high income potential, but very high washout rate. His they had a shirt that he had made that basically said on the back of it it said we're willing to do what you won't so we can live like you can't.

Speaker 1: 18:57

And it was kind of like a joke and it was kind of you know what I mean, Like it was like kind of a bragging thing. That's not terribly far off.

Speaker 2: 19:02

But it was pretty true, right. And I remember talking to him and he's like yeah, he's like, like in our industry, like dude, when you start you make nothing. He's like I made like 20 grand a year then he was older than me and he's like, not only that he's like, but I'm working 14 hours a day, going out every night with clients that are telling me no, over and over again, making 150 calls, five, six days a week. For a year and a half before I earned enough to basically not eat ramen noodles. He's like that's basically the first year or two of my industry, but you do that two, three years and you succeed in that like you can make a ton of money. Not saying that like that's the same as in freight brokerage, but like they're pretty similar.

Speaker 1: 19:43

Yeah, yeah. So Dave Ramsey has a quote that he says often it's live, what is it? Live like no one else, so later you can live like no one else. Like basically, do do what no one else wants to do now, just like the T-shirt Right, so later you can live and do the things that other people want and won't have.

Speaker 2: 20:02

One last quote on that Someone else at Southwestern used to say this he used to teach his kid this and I love this, and his son was like fourth time. And it was just if you do what's hard today, tomorrow will be easier. Do what's easy today, tomorrow is going to be harder. And if you really just boil it down to that today, tomorrow is going to be harder. And if you really just boil it down to that on like another. Another book I read somewhere said a similar thing. It's like if you're debating between two choices, the thing you probably are going to do is probably the thing you shouldn't, because your brain is almost always going to protect you and push you towards the easier thing. So if you just opt into doing the harder thing you don't want to every day, eventually you're going to get somewhere much farther than most.

Speaker 1: 20:37

One more quote, and I don't know who. I don't know who this is from, but it was. It's. It's very in line with that. It's choose your hard right Like, for example, it's hard living as a 300 pound obese person. It's also very hard to have the discipline to go on a diet and lose weight and do the exercise.

Speaker 2: 20:55

Only one has regret.

Speaker 1: 20:56

One has two pains. Yes, so choose your heart. It's really hard to make 100 calls a day and face rejection, and do that for a year, year and a half to build up a stable book of business. But it's also really hard to continuously fail at jobs because you're not applying yourself and you're never going to get the success that you want. Choose your heart. But back to expectation management, and this a lot of times I think it falls on the leadership, human resources, how the hiring process goes.

Speaker 1: 21:24

And this is one of the things that I loved when I started in brokerage. I left the trucking company, went to brokerage. What would become? My boss had me. After an interview, he had me sit down in the bullpen around everyone else that was making calls, like sit next to them, listen to them, hear what the conversations are like, just talk to them in between calls about like what it's like day to day. And what's funny is like first impressions are sometimes terribly inaccurate because, like I like the job, I was like, yeah, like I'm like I definitely want to do this, which I did, but like the actual people the one guy was like and that guy's kind of an asshole. I don't like. I like the job but I don't really want to work with them, ends up. The guy stood up in my wedding like you know, he like he came off a certain way and then we became like really, really good friends and to this day, like he's in leadership at another brokerage and as as am I. We've both moved on from that that one.

Speaker 1: 22:20

But back to the whole. The whole point is like if you're going to hire somebody and you want good salespeople, make sure they really understand what they're getting into. And it doesn't have to be job shadowing, but I, I highly recommend it. That's why we always tell people like, if you're thinking about getting a brokerage, like sit down with someone who's doing the job, take them out to coffee, take them out to breakfast or lunch and just like, talk about what it's like to do the job, how does it impact their work-life balance and their family life and how do they feel at the end of the day, what's like the hours and things like that.

Speaker 1: 22:51

And also like talk about you know, not even in just the shadowing part, but like in your interview process or your your recruiting phase. Like talk through people's comfort level when it comes to talk like hey, have you ever made a cold call before. Ok, you haven't. Ok, well, you know, maybe we should do some mock mock calls and just kind of see how this goes, and it's not like we're grading you on it, but just to like see, see how it makes you feel, cause we don't want to waste anybody's time.

Speaker 2: 23:20

So great thing and that reminded me of something. So two things that it reminded me of. One is this is a company I used to work. It's called Davison. They do, like you know, intellectual property, invention stuff, but it's it's a sales job, right.

Speaker 2: 23:35

And the thing I liked about their interview process is that's literally what they make you do, except here's how they set it up.

Speaker 2: 23:42

They put you in a cubicle, they give you a script, right, and it's really short and it's not like you really need to know it, and they're just like hey, here's 10 phone numbers call these people and like that's like the first 10, 15 minutes of the interview.

Speaker 2: 23:55

They just want to see are you willing to do it, how much hesitancy do you have? And one of the phone numbers is actually the vice president at the company and he answers the phone and you don't know that, right, and he kind of and he role plays through it just to kind of hear how you go. But I mean, the real value in that is to just see like how hesitant is somebody to do this, because, like the thing I always say to people that are getting into sales is like you learn your entire life that this is not something that is like socially acceptable. Like you don't you learn to not interrupt people. You don't walk over and just ask for things. You don't just go and try to like walk up to people that you don't know, like we teach our kids. Like you don't talk to strangers, like it's kind of ingrained in you that, like it's not a natural thing, right To do this.

Speaker 2: 24:40

And then you've got to just start picking up the phone and there's that other cliche it's like it's the 300 pound phone when you start, because it's so emotionally terrifying to start making those phone calls that like there's a lot of hesitancy and even for people that have done this like thousands of times, like it kind of really doesn't go away. You get into the habit of it, so you get a little used to it and then it gets easier. But if you stop for a month or two, starting again is like starting as if, like you've never done this before, like you got to get back into the rhythm, back into the habit. This isn't something that really comes second nature to most.

Speaker 2: 25:18

I've met a few people that kind of just don't have that gear and just could do that anyway. But also, to your point, like they're also the people that like I've hung out with and I like them and I could picture who these people are in my head. Like they're also kind of the people that like socially kind of make you feel uncomfortable in some ways because they just act in a certain way that is a little different than the norm and what people are comfortable Like they'll just ask any question, say anything that comes to their mind, like they just kind of don't have that hesitancy in them and like that's and I don't even think they're natural salespeople, but like that's really that psychological gear or whatever that makes it a little easier for some than others. Maybe you can call it extrovert, but I think it's a little different than that too.

Speaker 1: 26:03

Yeah, and even like, once you do hire somebody and you're going through trying to figure out, like so, let's say, you know, sales versus operations versus maybe a back office role, and this is not just for free. This is in any organization. If someone's a great cultural fit for your company and you want to retain them, but you identify that they're not great at that position, going through early on the repetitions of whatever the job is, that you identify, hey, they're not strong in this suit. The earlier you can do that, the better. It's going to save you time and headache and all that stuff and frustration. And save you time and headache and all that stuff and frustration.

Speaker 1: 26:35

And we did this at the first brokerage I worked at was we would just do mock calls, right, like we hire a new person and you know you start out with like we try to make it as realistic but not as like stressful as possible. So like, hey, one of us will go in another room, um, you'll, you'll sit at your desk, you'll call our phone. So you're not looking at me, right, it's going to simulate. You know you've got the ability to hang up and like, just not have to still be looking at it, right, and you just go through mock calls and obviously, like, when you know it's a mock call, you're still going to treat it a little bit differently. But you go through repetition of like um, the person on the other end that's kind of helping coach them up or like get them prepped or go through the reps, is going to throw curveballs at them to prepare them for when it actually happens, right? So the first time you get an objection on the phone from a customer, hopefully you've already thought through that objection generically in some sort of training scenario environment beforehand, right. And we know in freight brokering there's like 20 common probably like five most common objections that customers will give us.

Speaker 1: 27:36

Like we're not adding anybody right now, it's customer routed. What else do we got? Oh, you know we only use carriers or asset based carriers. You get like the standard ones that like you should know like how to bounce back at them, pivot, ask other questions, try to get to the root of it all. But if the first time a rep calls and someone's like hey, we're actually we only use asset based carriers, if their response is OK, have a nice day, like that's. You know you didn't. You didn't progress at all, you didn't learn anything? You didn't move the needle at all, so I think so, outside of expectation management, that goes to your training piece right, like how is this person being onboarded, trained, guided, et cetera?

Speaker 2: 28:17

And here's the other thing too. Right, we talked a little bit about this, but I really do think mindset is the first thing and everything kind of comes from there in a certain way. Right, Because, like and I say this at the end of every show, and like somebody said the other day that hears me say it didn't realize why I said it and I'm like no, like, literally everything you do in your life starts with whether or not you believe you can or you believe it's worth doing. Until you can do it. Right, Like if you don't, and you don't think you're going to succeed, you have almost no shot. Right, Because as soon as it gets tough, your brain is going to convince you to do something else. Right, You're going to jump into something else. Right, and it's like I somebody said this to a client of mine that they reiterated to me yesterday. Somebody said this to a client of mine that they reiterated to me yesterday.

Speaker 2: 29:07

My client went and spoke at this event and she got all these referral partners. It was an event for people that would refer business in her industry. Right, Got all these phone numbers, text all these people, but the person that set it up is kind of sells to the same group of people and he said to her like well, you know, these people get bothered a lot and they get sold everything, so try not to bother them too much. And she asked me she's like, so, like what should I do? Like I don't want to be a pest and bother them. And I was like well, let's take a beat for a second. I said because, first off, if you are thinking that you're bothering people, like you've already lost because you are not going to succeed in sales, that is the job. The job is to meet and touch lots of people over and over again until they know you, trust you and like you and want to work with you. That is the thing you're trying to get towards.

Speaker 2: 29:59

And if you perceive every time you go to work is I'm bothering people, then like that mindset is going to prevent you before you even start, Like you're already not going to win as far as I'm concerned. Because that's what you're thinking every time you pick up the phone. You're not thinking I can help this person. You're not thinking I have a solution that could help this business. You're not thinking I believe in the product or service I'm selling. You're thinking I'm just calling to irritate people. That is a very long day. If you define your own job as I'm irritating people all day like you're probably not going to win and you probably aren't going to stay there that long. Right, and I genuinely think like that's why when people sell a product or a service that they believe in or they believe they can help somebody better than their competitors, they are far more likely to succeed, for a number of reasons. One they're more convincing.

Speaker 2: 30:51

Two human beings are the best lie detectors. We can snuff out and smell BS, whether that person realizes they're doing it or not. You can hear and feel whether somebody is being genuine, because your entire life you do that, and that comes through the phone. It comes when you see somebody in person. So you're not going to work with that person. You're not going to do business with a doctor that's like oh well, come in, I'll see what I can do. I'm not really sure, but maybe we'll be able to find out what's wrong with you. You're probably going to call and schedule an appointment with someone else, right? It doesn't matter what that is Dude.

Speaker 1: 31:23

So I was telling you off air, like I just I just traded my car and got a new car this week and you know, like anyone who's gone through the car buying process, like you've probably had a good experience with one kind of person and you could sniff out the bad ones right away. So like sales rep we worked with her with my wife's car last year, so and it's a friend of a friend that we've met so like very smooth process, no bs, um. But like I'm going to pick up the car and gotta go talk to the quote-unquote finance manager, aka the guy trying to sell you the super expensive extended warranty, and like two seconds into it I was like, oh my god, how do I get through this stupid PowerPoint? I mean, hey, if you sell cars or you're a finance manager out there, so be it.

Speaker 1: 32:11

I have just, you know, I just take care of my vehicles and I have never, you know, the one time that I ever bought a super expensive extended warranty, I did not get my money's worth and I never did it again. I've never had an issue. So I just don't buy them. Um, but he's going through this whole thing with me and um, I was like look man, I was like I appreciate it. I said, but I'm, you know, I'm not an extended warranty guy and he's like okay, he's like we can just skip that part then. But it was like just the way he made me feel it made it so awkward and uncomfortable, um just because like it comes across self-interested.

Speaker 1: 32:46

Oh yeah, and it was like it was almost like it was a hidden pitch, but I knew it was coming, because that's how it always is when you buy a car. He goes through like oh yeah, here you know, great, great truck you got. You know. I'll just kind of show you some of like the expected maintenance costs over the years and blah, blah, blah and um, then slowly I'm like here it, here it comes, and then he starts talking about the platinum package. And I was like you, son of a bitch.

Speaker 2: 33:10

What's funny is and it's a good one because I remember the portion of mine and it's funny because I was just telling you there's a screw in my tire. Right now my wife's literally getting her the tire fixed on our car and when the guy was pitching the wheel and tire package it's a warranty right To replace wheel and tire damage and the way he pitched it to me was oh well, it's only 45 bucks a month and it covers any of your tires and wheels for any damage. And, like, your wheels and tires are pretty expensive. And I was like, yeah, that sounds about right. And then I said, well, hey, let me ask you how much is a rim and how much is a tire right? Said, well, hey, let me ask you how much is a rim and how much is a tire right?

Speaker 2: 33:48

And then he tells me what the number is and I was like, well, how long is this term? Well, it's three years. And I just multiplied that number times the three years every month and I was like, well, that warranty costs as much as replacing three wheels, right? And he goes well, yeah, I'm like I don't think I've ever damaged one wheel, let alone three, inside of three years. Like I kind of feel like that's probably not going to work in my favor.

Speaker 2: 34:12

And then he tried to convince me that, like, the 35 or 45 bucks a month is such a low number that I should pay it anyway. And that is somebody that's self-interested, right. But if he would have approached me and said, hey, have you ever had any wheel damage? Have you ever hit any potholes? And I may have, if I was one of those people that have done that once or twice, he might be like, well, hey, it's a little cheaper to just pay this a little bit every month than to end up with a $2,200 bill to replace a rim and a tire. Ok, now, that is something that could be valuable to me if I'm in that category. But when you approach it by trying to convince me that $35 or whatever dollars a month is just better than me waiting to pay if something goes wrong. You can tell that that guy's just trying to sell it to you to make money.

Speaker 1: 34:55

Right, it's how you approach the situation 100% Qualifying is what that is, by the way.

Speaker 2: 35:01

Qualifying a prospect to see if they're in need of the service that you can sell them.

Speaker 1: 35:07

So what this boils down to is it's like the way that you're communicating and how it comes across. Like you and I have both read Chris Voss's book Never Split the Difference and I highly recommend it. If you're in sales or you're thinking about it, it's a great. Even if you're not, it's a great book, fbi Negotiator, and it's all about communicating. And you can get the same message across by tweaking some of your words and it it's received like the.

Speaker 1: 35:31

The context is still there, but it's received vastly different depending on how you word it. The tone of your voice, the inflections, all of that stuff, the volume of your voice, um, your energy, all that. And I think that, like, we've all had we've all had like the the rope, not the robo call, like the telemarketing call that like is just so bad. They're reading off a script, they sound like a robot and, like you're, you're debating your head like am I rude if I hang up right, because I don't want to get to the end of their pitch here? And we've probably all had that phone call where, like you don't feel like you're being sold to, but like you are genuinely interested when what the person's like talking to you about. And that's the difference between someone who is, um, really fine-tuned their communication, their ability to build rapport on a phone call, versus someone who just says what you know. People ask us like do you guys have a script? It's like we don't want you to use a script for this exact reason, but anyway, I digress.

Speaker 2: 36:30

No, because I'm going to pull on that thread a minute, but there's a guy worth looking at on LinkedIn for anybody. His name is Josh Braun. He actually lives right down the street from me. I didn't know this when I found him on LinkedIn. Great sales coach, puts out great content on a lot of stuff we're talking about Really good daily tips. He has some products, too, I think, like flashcards and things that help you like work on these skills that are really effective. I hadn't bought them recently, but I looked into them a few years ago and really great stuff out there if you want to learn more.

Speaker 2: 37:00

The other thing that I was thinking of is there's like those two really skill sets we're talking about. Right, what is getting better at communication? Right, your communication skills, which is not just what you say, but how you say it. Right, there's lots of studies that say, like 90% of communication is not what you're actually saying, it's how you say it, whether it's your mannerisms, it's your tone of voice, it's your inflections, which is funny because remember when we copied my voice on 11 labs to see how AI would do like it misses all the inflections, it misses all the tones of voice. Even though they're there, they're in the wrong place. You feel that it is off, right, yep, you can't. And then if you dig in, you can see right, those are the things that, like you, only, I feel, get better at it, pract, are at it, practicing.

Speaker 2: 37:42

Like I was interviewing a few people that had not been in sales, that wanted a job yesterday, and they're like well, what is the first couple of weeks? Look like I'm like you just got to keep falling off a bike Like you've got to. Just that's how you learn to ride a bike. It's not when it works, it's when you tip that you learn not to do that again and little by little, you get a feel for how to ride it. It's the same with your verbal communication. What is your inflection? What kind of feedback do you get? Because, like one of my favorite things I learned from my sales coach a long time ago is like if you keep getting the same objection, you are saying something that is eliciting that objection.

Speaker 2: 38:18

All communication is is a dance. You're doing something, they're doing something, and if you keep getting the same response almost all the time, if you record your call and listen to what you said before that objection, you said something that piqued their guard that made them go wait a minute and then they came up with an objection. So when everybody, especially new salespeople go well, I keep getting the same thing, this is just too hard. Or like nobody wants our service. They never want to take the responsibility to look at their own behavior and then improve it because, like that is an opportunity. Getting the same objection over and over again is a good thing. It's like missing a free throw to the left every time. Okay, well, now I know I consistently miss to the left. I got to move a little this way, right. That is why I feel like practicing this and making calls is the only way to get better at. It is necessary and is how I think.

Speaker 2: 39:09

Secondly, reading books and content gives you better context to understand how you're doing what you're doing. It's not going to give you a blueprint to do this every time, but it's going to give you feedback. So you know like oh, I keep doing this, I keep hearing this. Oh, this makes sense. That book is saying that, like, I am probably doing something like this, and then you change your tone a little bit every time. That's why, when you work in a, they call it like a bullpen or in a sales pit. They put all those people together. Why? It's because you learn from each other. You pick up what the person next to you is saying, you hear their tone of voice, you're voice, like their openings a little different and, without even realizing it, you just start to try what they're doing and then you feel, if that works, then you try the person to the right of you, Then you hear the person over there, then you try a little bit of that and eventually you come up with your own personal mix of how you communicate that fits you and your personality, right, is, I think, super important.

Speaker 2: 40:04

The other thing that I wanted to say is like we learned I probably I don't remember when I learned this, but it was probably within a few years of being married but my best friend, who I grew up with and learned sales with and who's still at that company, right, like we used to use the sales techniques on our fiances and wives, just cause, like it's a habit, right. Like you do it all day at work for eight or nine hours a day, like we would do. Like closes, you do like different techniques that we would learn and like what I noticed was some arguments or disagreements I would still lose. But when I would replay to my head, I'm like, no, like, if that was a sales call, like I hit the inflections, I had the body language, I'm like I did exactly what I would have done and that would have worked nine out of 10 times, right. And then I realized I'm like, what was different about it with my wife than in the sales call is she knows me better and she can feel my feelings better than a person that I don't know as well. And then I realized that the solution wasn't just how I was delivering the message, but it was how I felt and what I believed.

Speaker 2: 41:13

And when I shifted how my intent was not just how I was saying what I was saying we communicated more effectively and there was less disagreements because I'm like, oh, I'm saying this and I'm selling the shit out of it, but she isn't buying it at all and she's still mad.

Speaker 2: 41:30

And then I realized, like, when I thought about my thoughts that were underneath what I was saying, I was like, oh, I didn't believe that at all, like I was just saying that to make them feel better. Right, I tried to sell the shit out of it, but I didn't believe it. And then, when I shifted my belief to believing what I was saying, like there was no more disconnect, and she could feel that disconnect. And it was like this great learning feedback where I'm like, oh my God, I get to practice this every day with honestly higher stakes and more repetition. That made me realize how much your mindset matters in this context of sale and everything you do. But when you realize there's lots of places to practice this in your daily life we talk about, like cashiers you talk to a bartender, a waitress, interactions every day, a caddy at a golf course, wherever you're at like, there's plenty of ways to develop this skill when you realize it's the same skill you're using everywhere else in your life.

Speaker 1: 42:24

So you actually just brought up two things I think were great the cashier one and the caddy one, because these are literally two that I've done in the last week and I recommend I mean not everyone's going to have a caddy every week, but like cashier gives you a really good like the two minute conversation, right, the short like real quick service level, but you're building some rapport conversation.

Speaker 1: 42:46

The caddy one um much longer, like I when we golfed last week you were required for the group, Right, so it was like four or five hours so we start off and it was, like you know, this kid's 24 years old.

Speaker 2: 42:58

We're like we don't really know and like it's kind of like a strange, just like a sales call by the end of it.

Speaker 1: 43:04

Ben, we had this dude teeing off with us on the 17th and 18th. He's always like they just can't see me when we get up by the clubhouse, but we were able to build rapport. We learned all about his background and what he wants to do with his life and with golf and all this stuff and it's like there's probably a he told us too. He's like you guys are awesome. He's like there are people that will come out here and they, you know they don't want me to do anything except for read their putts for them and then they'll yell at me if I, if they didn't make the putt, and blah, blah, blah. And it's like that's the um self-serving version versus the. That's great, the opposite, right. So two different experiences. Um, but yeah, like. But back to like the.

Speaker 1: 43:49

Because you're gonna have, you're gonna have your short phone conversations. That's your, you know, do the reps by talking to 7-eleven when you're checking out with your monster gatorade, whatever. Or if you're at your you know, publics or grocery store, whatever you, wherever you shop, for two minutes. Um, if you're, uh, your longer conversations, maybe it's a meeting with, with a panel or a board member, or it's an in-person visit or whatever, because those conversations are very, very, very different.

Speaker 1: 44:13

We actually had someone commented on YouTube saying, like for a topic idea was like how about the do's and don'ts of an in-person customer visit? Because, like, they're very different than a phone call, because you're there for a lot longer, you're probably going to have time to start talking about things on a personal level that you never had the chance to before and like dig deep into them and there's definitely some some, some areas to avoid or maybe lean into to help build rapport. But yeah, the practice and all this is like, I think, a huge reason why people don't do good at it, because they don't know where their weaknesses are, they're not getting that feedback, they're not putting the reps in and they just kind of stay like at a plateau.

Speaker 2: 44:52

Here's the other question. We get a lot right. There's like graphs that will show this. You can look up places that it's like hey, as your knowledge grows up, goes up as you do a job, longer your confidence increases, and then you can sell more because you have more confidence, because you've done this more, you believe you can do it. So that comes across when you're selling Right, and I think that is true. But the common question we get is I'm new, I don't know how to do everything yet. I don't feel confident in myself. How am I supposed to sell Right? And I think that's a great question, right? And I think the short answer is you don't have to know everything to be confident in your ability to work harder than your competition, and I think that is more important than knowing everything and being lazy. Just leave it at that.

Speaker 2: 45:42

Right, Because if you are picking up the phone and calling somebody, and I don't care if you've never moved a load before, but you believe that you are willing to do more to help this customer than anybody else that's working with them. That confidence is sufficient to get them to work with you, and most people will appreciate that. If you're even honest, like look, hey, just been in the industry a little bit, but I can assure you that I will be available 24-7 if you call me and you need anything. I will work harder than anybody else you're currently working with to find you what you need, to make sure you're getting what I tell you you're getting, and I will be the first person to tell you. If there's a mistake or I can't, I will be honest, direct and upfront with you. If that's the case, right, that is confidence without knowledge, and that, to me, is way more valuable than the person that has done this 10 years but is too lazy to work as hard as the person next to them.

Speaker 1: 46:33

I remember one of my first actually it was my first sales job ever was at Best Buy selling. I started in home theater so like TVs and stuff like that and shadowed for like the first week listening to how the the guys on the floor would like talk to customers and answer questions and pitch certain things. And I remember like after a week the guy that was training was like he's like, nate, he's like he's like you're ready, let's take, you're going to take this next guy. And I was like I'm not ready yet. He's like you're ready. He's like just remember, you don't have to know everything, you just have to be confident that you can get them an answer and you know, just know the questions to ask and whatever you don't know, like we'll be able to help you out. So he just kind of like threw me starting point and was within like and we weren't commissioned based at Best Buy, we did get like they did like a quarterly profit sharing based on your store, I think.

Speaker 1: 47:33

But like within a month or so, like I remember, I put together like this twenty five thousand dollar home theater deal for this guy that just moved into Buffalo from DC, like badass TV, surround sound system and receiver, top of the line, like cabling and wireless, everything, and, like we did, the install, calibration, all the warranties, like everything on it Right, because the guy was just like you really seem to know what you're talking about and like you know I trust you know, I trust what you're telling me. So I mean I didn't like screw him out. I think he set up with a sick, a sick setup for his house, which is what he came in for. But that was literally the. In a period of like probably four or six weeks, I was able to transition there from being afraid to have my first conversation with a customer that's looking to buy a standard TV to some dude that's got deep pockets trying to set up his new house. So, and you have to start somewhere and, you know, make the adjustments from there.

Speaker 2: 48:29

That same line. I still remember my mentor at my first job I was working at a bank and same thing. Like we're going to go out and meet customers, going to go start talking to people on our own, and I remember him sitting me down and saying the same thing. He goes, listen, people will ask you questions you don't know the answer to. He said first the worst thing you can do is make some shit up, Lie. Yeah, the worst thing you can do is pretend like you know and tell them something you don't. Right, he's like I'm going to give you a line that will bail you out of this in every scenario. That's a great question. I want to make sure I give you accurate information. Let me go run that down, Let me go confirm that, Let me go check on that and see, and I'll get right back to you and then write it down.

Speaker 1: 49:14

Yep, I had the same. Like, literally, in the military they teach us the same thing, like if you're giving a briefing and the boss asks you a question you don't know the answer to. Don't lie, don't say I don't know, say basically I don't know, but I will find out and get back to you. So some variation of that. The one other so I wanted to I don't want to run out of time here the one other thing I wanted to hit on, at least briefly and this applies to all um industries, but I'll hit on freight specifically is um, if you don't understand your environment, like your market or the operating environment that you're in and you're not staying up to date with it, that can get you into trouble too in sales, especially if you're brand new and you don't take an interest in learning about it. Let's say it's solar and you don't know where. Or you don't understand what the rebates are based on, where you're located, if there's a state rebate or the federal rebate, if it's selling houses and you don't understand the mortgage interest rate environment. Or if it's freight brokering and you don't understand what the spot market's like versus where's capacity tight. What kind of regulations are impacting us right now? Where have storms impacted certain parts of the state or the country, right? So not only does knowing that stuff help you understand why things are the way they are, it helps you bring up conversations and discussion points to make your conversations flow easier.

Speaker 1: 50:33

So like, if we know that capacity has been super tight outbound in a certain city and you're prospecting business there, which is a great place to prospect and for a great reason, that could be really your discussion point. Like, hey, I've been talking to a lot of folks who've having a really tough time getting reefer capacity out of your area. Like I've already laser focused the point of the conversation. And you know it's not like it's a magic line where it's every single time they're gonna be like, yes, please find me a truck, but at least like you're hitting on a point that, or you're hitting on an area of the conversation that is more likely than not relevant to that person. So, just generically speaking, you know, take an interest. Like whether it's you know DAT has great market insights. They have great reporting on their analytics tool. You've got like newsletters, right, you've got our newsletter Freight Waves. You've got all Freight Caviar, whether or not they're meme-based or all factual, just understanding what's going on out there is going to be massively important to help you succeed.

Speaker 2: 51:45

It reminds me, right? I'll kind of end it with this Like the things you shouldn't do is start a cold call by telling them everything about you and everything you can do without knowing anything about them, right? So like you get a cold call and somebody's like hey, this is Jimmy from HVAC service, we can handle indoor, outdoor, we can replace your units, we can service your air ducts and we can come out and clean them. I wouldn't respond to that with hey, this is Ben Kowalski, I work at a freight brokerage, we can handle your FTL, ltl, drayage and international.

Speaker 2: 52:15

And he's going to be like well, why is that relevant? I'm going to be like I don't know. Why is what you just told me relevant? Right, like you don't know anything about me, you're just calling me, telling me everything you can do, without asking me whether or not any of these things matter to me right now. And it's like in any scenario that sounds super awkward, like if somebody just introduced himself hey, I'm Nate the Baker and we can make buns, rolls, this, and like, okay, but like, I don't need bread right now, but I'm glad you can make cakes and cupcakes.

Speaker 1: 52:43

Yeah, we had a guy used to work with it. It was funny because the rest of us, when we would hear him do this, we would all like look at each other and chuckle. He would go through and give this like spiel of the history of the company and we're all like we've been in business Nobody cares what year we were founded in, but like again, like giving them the feedback on it, he probably never would have adjusted course, but yeah so anyway, family and business.

Speaker 2: 53:10

We've been in business for 40 years and well.

Speaker 1: 53:13

So I will tell you this like there is a time and place to go through some of that, some of those details, but not right off the off the pitch. So like, for example, when it comes to like it like appears, we're agent based pitch. So like, for example, when it comes to like like at Pierce, we're agent based. So like, a big part of what we deal with is people that are, you know, considering coming to our company right Like, so we have to vet these people out and then, a lot of times, you have to like make them feel comfortable that hey, we're actually a great company to partner with.

Speaker 2: 53:41

You're addressing a risk, you're preempting an objection.

Speaker 1: 53:44

Hey.

Speaker 2: 53:45

I might be worried that Pierce is a fly by night agent program, that if I bring my customers over, you guys are going to disappear in a year and a half. Right, that's the risk that you're going to address.

Speaker 1: 53:55

So so, when somebody reaches out and wants to talk about, like, hey, well, you know what's it like to, what would it look like to come over to your company, I usually start off and this is, you know, you can tweak this however you want and it's gonna sound different when you're selling to a customer or a shipper. But I'm usually like, hey, what made you decide to reach out? Right, like very basic. It's not like, hey, thanks for reaching out. Our company was founded in 1981.

Speaker 1: 54:18

But when we get further into a conversation and this will apply to your, you know, selling from a brokerage to a shipper is, if they're, if they're showing signs that like, hey, I, you know, I want stability.

Speaker 1: 54:31

Like stability is important to me in a relationship. Look, we, we've been doing this for, you know, 30 years now. We know what works, we know what doesn't work. And that can apply when you're selling to a shipper, right, when you're selling to a shipper, right. And they're like, if, if they're worried that, like you're going to go out of business, not pay a carrier, and then that carrier is going to end up coming back to them looking for a freight bill to be paid, like, even like TQL, right, we've been around 25, I don't know how many years TQL has been around. I'm like we've been around a long time. We're a very large company. We've got a lot depth across the board. So it's you don't start off with that but it's a, it's a reassurance to somebody if you're sensing that that's a potential fear of theirs. So, but yeah, I guess you could also sum that up with know when to say certain things and when not to say certain things.

Speaker 2: 55:18

So yeah, and it's like you can sum that up with that other cliche it's like God gave you two ears and one mouth. Use them proportionately, right, like you should be listening twice as much as you're talking, and not listening to respond, but listening to understand. Right, and they're very different. When you're just sitting there thinking about the next thing you're going to say while someone else is talking, you're listening to respond. When you're listening to understand what you're communicating to me, then I can respond with something that is relevant to the thing you're thinking of. Right, it really is. Otherwise, like you're not really communicating, you're just talking at each other. Right, you might as well be having a monologue by yourself at somebody else giving another speech, and then at the end you both walk away, not learning anything about the other person. Like that is not sales, that's not even communication, a hundred percent.

Speaker 1: 56:07

All right, well, cool, good episode. We got into some good, some good points there. Hopefully you guys can get some good takeaways. Let us know what you think in the comments or review, or send us a message and let us know some future topics that you'd like us to talk about. But, ben, any final thoughts here?

Speaker 2: 56:24

Whether you believe you can or believe you can't, you're right no-transcript.

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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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