Seriously, Here’s How You Keep Millennial Truck Drivers

Here's How You Keep Millennial Truck Drivers
Photo by Brooke Cagle on Unsplash

So many words are used to define particular generations. Baby boomers, Gen-X, Gen-Y, and now it’s millennials, millennials, millennials. There’s an inherent danger in lumping a huge group of men and women together based on when they are born. But this is America, and we seem hooked on looking at things with a generational eye.

What Is A Millennial?

There’s a real consensus that the birth of the millennial generation started in 1981. The end is a little vague. For the sake of this discussion, I’m sticking with 2000. This would mean the youngest of the generation is either just starting their working career or finishing their education.

Kris and I have raised 3 kids, all born in the 80s. I’ve also hired and trained more than my share of millennials for everything from truck driving to handling livestock. I also have more opportunity than most to meet young drivers who’ve tried the OTR route, but just didn’t like it.

I’ve also spent more time than most studying this generation, separating the more common traits from the negative propaganda that’s all over the web. Let’s break down some of the common traits of this generation, and see how we keep them from churning from company to company.

Millennials And Technology

Old truckers like me look at new technology in trucks today as micro-management. Big brother is watching us. Millennials think otherwise. Automated transmissions, electronic logs and modern telematics are just fine with them. After all, they’ve grown up with technology.

Does your technology communicate directly with the driver? Younger drivers are best served when recommendations for improvement come directly from interactive technology, not a corrective phone call. I’ve worked first hand with one of these systems. The system allowed me to make changes that not only increased my safety ratings, these changes increased my monthly bonuses. Everybody wins with this!

Flexible Schedules And Work-Life Balance

One gigantic change in the industry came in 2003. That’s when we were handed the 34 hour restart rule. Trucking companies just couldn’t help themselves, and time off at home became 34 hours for many truck drivers. Prior to that, a decent weekend at home was easier to be had.

Millennials as a whole are looking for work-life balance. Trucking companies really need to think outside the box on this one. What can you offer that creates a predictable schedule with real home time? Be creative. There should be plenty of options.

  • A long weekend every month, Friday through Monday.
  • Running local, home every night one week per month.
  • 7 on, 7 0ff options – without calling it part time and no benefits. Seriously, if management doesn’t think they’ve performed 80 hours of work in 70 hours of on-duty time, think again.

Meet with a few drivers. Have some brainstorming sessions and see what a collaborative effort can create.

Is Your Culture Message Failing?

Millennials are more socially aware than previous generations, largely due to technology. Smartphones, social media and the 24 hour news cycle are something this generation grew up with. They’re also big on corporate culture.

You might have a great company culture at the corporate office, but it’s mostly lost on the drivers. If all they see are visuals, emails and messages on their tablets, it’s not even a dialog. How can it be a company culture?

Drivers from several large companies have told me this comes off as impersonal, mimipulating, even phony. They see it as totally staged. The driver isn’t part of the office staff or emotionally connected to any team within the office. You can’t share a common work culture without relationships.

Why not use the very technology that millenials know and love to drive the company culture message home? When was the last time you’ve had a video call with one of your drivers? Most of your drivers use some form of live chat, Facebook or otherwise, several times a week. Fire it up from time to time.

The 70-30 Rule Doesn’t Apply To Trucking

Most people under 40 agree that as long as they find satisfaction in 70% of their job, they’ll tolerate the 30% that is unpleasant and unrewarding. Although this may be true in corporate America, it’s certainly not true in trucking, and the reasons are obvious. Let’s look at a few scenarios.

  1. Stuck in rush hour traffic.
  2. Driving cautiously through snowy conditions, at slower speeds.
  3. Driving on a 2 lane highway with too many stoplights, just to avoid toll roads.
  4. Sitting in line for 30 minutes or more at a mandated fuel stop.
  5. Searching 2 or more truck stops for a place to park.
  6. Waiting in line for a dock assignment. Or worse yet, sitting in the road for an hour or more to get checked in or out of a warehouse facility.

Like any other job, trucking has its share of irritations. However, there is one big difference. In each of the above examples, the driver is either making less money or nothing at all, even if what he’s doing is saving money for the company.

We’ll get back to parking, but what can be done with the others? The real answer would be an industry wide change in how drivers are paid, something that will take some time to iron out. But what can you do to address these now?

For example, if a driver is averaging 50 mph because he’s saving the company $75 in tolls, why not pass on some of that savings? Split it with them. Give them a reward for their efforts. No one likes being purposely paid less to work longer and harder.

Part of the 30% could be one of your regular accounts, traffic lanes or delivery times. Again, have a few drivers help you identify these so you can address them. It’s likely you could actually remove a few of these areas by dealing directly with the shipper or receiver.

Everybody Gets A Trophy

The millennial generation grew up with participation trophies. It’s part of their culture. You can love it or hate it, but deal with it. They love recognition. It doesn’t have to be a trophy, but a little attaboy goes a long way.

Like many of us, they also dislike the annual quarterly or annual review thing. I agree with them on this one. Why would my supervisor wait a year to tell me what they like or dislike about my job performance? And who wants to be marked down for running out of hours while trying to find a place to park, or waiting on a flat tire repair?

Off Site Training Events

Does Your Safety Meeting Look Like THIS?
Photo by Product School on Unsplash

Nearly everyone I talked with in other fields, and earn more than 40k a year, attend 2 or more off-site events each year at company expense. People skills, health and motivational training seem to be common themes. I’m guessing most employees in your corporate office have attended at least one in the last 12 months.

What do truck drivers get? Safety meetings. The baby boomers know these meetings happen once a year to meet DOT requirements, and a second time for the insurance company requirements. Our rule is don’t ask questions, it’ll be over sooner.

Millennials are into self-development. Hire a speaker, cater in a decent meal and show them you care about them more than your insurance rates. Resist the temptation of using inhouse talent for this. You’ll grow better as a team when you learn as a team.

The High Anxiety Generation

This generation has more anxiety issues than others. We’ll save the why for another conversation, but it’s a fact. Once more, the 24 hour news cycle and social media definitely play into the cause.

I’ve spoken to several drivers who’ve left the road for local jobs because of anxieties over parking, driving in big cities, even navigating mountains in western Montana and Tennessee. You may be hiring and training men and women to drive a truck, but you could be failing in teaching them how to be truck drivers.

Most of the anxiety issues could’ve been addressed with better training. It’s one thing to hear how to use the service brakes along with the engine brake, hauling 80,000 pounds as you’re descending Lookout Pass. It’s quite another to actually do it with someone who’s done it dozens of times.

Once again, getting together with a few younger drivers could easily identify the high anxiety issues. Training, proper use of truck parking apps like Trucker Path, even having a company paid parking spot reserved when needed, could all help keep these drivers on the road.

Side Note: I challenge you to download this app and look for a truck parking spot when your drivers are trying to figure out where to stop for the night.

Orientation – Part Two

A driver is hired, then sits through a few days of orientation. After being overloaded with  new information to process, the new driver is issued a truck and given their first load. After a couple weeks on the road, we all have questions.

  • What does the load planner do?
  • Why is the safety department so big?
  • Where do those tablet messages come from?
  • Who sees the messages I send back?
  • Can anyone help me figure out where to park?

Have an orientation, part 2? Give the new hires a chance to meet the team. Who’s finding all those loads through brokers? Could the sales rep who services your biggest dedicated accounts shed more light on how to best service them?

The One Big Thing, Communication

An expectations conversation is a great segway between lowering anxiety and opening the door to communication. It’s a  powerful tool in two people learning to understand one another’s goals.

This has been a game changer for me more than once. Sadly, I was the one who instigated the conversation each time. It’s a concept I used years ago when the oldest millennials were still in preschool.

Every dispatcher, driver manager or whoever your driver answers to, needs to be clear about what they expect from their drivers. That same dispatcher needs to know exactly what the driver expects from them. This is also where you ferret out any  expectation a recruiter might have promised that you can’t meet.

This meeting needs to end with two people knowing the other one has their back. PERIOD! Get this right and everyone wins.

When was the last time you sat down with a driver and asked what he or she expected of you? The relationship will only succeed when you both know what’s expected of each other, and have a true desire and ability to meet these expectations.

The expectations conversation needs to happen with every driver. And it needs to be a two-way conversation. After all, when either of you fail to meet the expectations of the other, that driver is job hunting. Oh, and he’s job hunting with that same phone you refuse to call.

A Few Times You Really Need To Call

  • Any time a driver has been at a dock an hour after their assigned time.
  • When you’re about to send a new dispatch. You don’t have to do this every time, but do it often.
  • Any time you’re redispatching your driver while enroute. Don’t expect them to pull over, then read the message you sent.
  • When it’s time to get them home. Call and tell them what their load home is, and when they can expect to actually be home.

Never Send A Message Without A Name

Good, bad or ugly, no message should ever be sent without a name. Good news or bad news, own it. Put your name on the end of the message. Seriously, drivers know some messages are canned and computer generated. Those do nothing in relationship building. The name at the end makes it a note between two people rather than a computer system talking.

Get Comfortable With Video Calls

Obviously, you’re not going to have any kind of video chat with a driver while they are on the road. But there are a few situations where this could really help. The most obvious situation is when the driver is sitting at a shipper or receiver and things aren’t going well. Now you can really communicate some empathy. What a great way to let them know you’re in this together.

Embrace The Suck

The Navy SEALS use this saying, and I use it when it applies. There will be times when you know a load is going to be difficult in one way or another. Maybe the last three drivers that picked up from a shipper ended up sitting for 4 hours… and it sucked.

This is the perfect time to embrace the suck. Rather than let a driver be blindsided, (then totally ticked off) give a call, warn them of the situation and ask for updates. Let them know you have their back. Don’t ignore the situation, dodge the phone calls or handle it with electronic messages. Own it and be proactive.

Benefits That Match Expectations

Pay, benefits like vacation and 401K programs need to be competitive and reasonable. Not just in your eyes, but in the eyes of a younger generation.

Why would I drive your truck for 24 months before I can get 2 weeks of paid vacation? And why is the vacation pay lower than the average working week. Certainly, you don’t do this to the office staff. How about a week every 6 months? It’s part of what keeps me with my employer. I can take it, save it up or cash it in.

Offer a week every 4 months after 5 years. It’s hard to start over with one week after a year when you have 3 weeks of vacation in the near future. Be creative.

Defined contribution retirement plans also come to into play in the retention department. Companies need a decent match and a shorter vesting period. Quite often, millennials may also be looking for some socially conscious 401K options. What options are you giving them?

Other little things really count when drivers are considering whether to stay or leave. Little things really add up. Be creative.

  • Work boot purchase reimbursement
  • Monthly cell phone allowance
  • Laundry reimbursement for drivers who stay out longer
  • Pay a driver back for a couple of paid parking spots each week
  • An Uber allowance to go to a real grocery store. Again, for drivers who stay out longer

Again, be creative with ideas from drivers. Experiment and see what works.


  1. Millennials are cool with new technology
  2. Offer more flexible work schedules for work-life balance
  3. Your company culture needs to be more than a message
  4. The 70-30 rule doesn’t work with trucking
  5. Immediate recognition
  6. Off-site training events with hired speakers
  7. Deal with their higher levels of anxiety
  8. Communicate, communicate, communicate
  9. Meet expectations with company benefits


It’s all going to be okay. The millennial generation is more than ready to take on the future with you and your trucking company. They’re prepared for the technology and automation looming ahead. They’re prepared for the multicultural face of the trucking industry. I’d even say they’re better equipped to communicate the culture message of your company and draw a more diverse workforce.

They see no shame in profit, but they’ll call you out on an insincere line of bull when they hear it. Part of their exchange for loyalty is transparency. Like it or not, they’ll soon be running the lion’s share of trucking companies. From driver to CEO, we baby boomers will soon be turning over the keys to the trucks and the corporate headquarters to them.

Side Note: We talked about this in our latest episode of The Trucking Podcast. You can check it out by following this link.

Research Sources

I’ve spent a lot of time on research for this piece. The articles  Forbes and Mental Floss were among the most useful. Kris and I have also raised 3 kids, all born in the 80s and with a wide variety of lifestyles today.

I’ve also hired and trained millennials as laborers and truck drivers. Part of my current job includes training both new and experienced drivers as trailer spotters in a large shipping facility. About 70% of these were born after 1980, making them a part of the millennial generation.