Challenges for 2026

I asked ChatGPT about the challenges truck drivers might face in 2026, and it mentioned a ‘persistent driver shortage!’
I was a bit surprised and asked, ‘Really?’

It seems like my customers are finding it tough to hire or are being super picky because there are so many drivers out there. I reckon the trucking industry, especially the cross-border stuff, has taken a hit. There aren’t as many trucks crossing into the US as before, which is probably because the economy is slowing down. We won’t go into the reasons for the slowdown in this article, but I think there are more drivers searching for homes right now than there were a few years back.

If ChatGPT’s perspective on the driver shortage isn’t quite right, did it get anything else right?

The second thing ChatGPT talked about was keeping drivers. I think it’s a common issue for many trucking companies in Canada. How do we keep our most valuable resource?  First things first; pay is key! To keep their top drivers, trucking companies need to offer competitive wages and health benefits. (Sorry, Driver Inc. employees, no benefits for you!) Another way to keep drivers happy is to really listen to them. I mean, not just talk to them, but really connect with them. Management should try to understand their truck drivers. This means sometimes management should be out in the yard, just chatting with a driver. You could even help them fill up the truck. You could also get involved in their vehicle inspection; encouraging them to do it. These outdoor activities work especially well when it’s not too nice outside. It shows that if management is willing to go outside in bad weather, the drivers should feel like they can be active participants too. And when you engage a driver in their natural environment, whether it’s in the truck cab or in the yard, they are more likely to talk to you and give you honest answers. After all, they’re in their element and you’re out of yours. If you bring the driver into the office for a discussion, I don’t think it’s quite the same. Now, the manager is in their usual environment, and the driver might feel a bit uncomfortable being out of their element. Sometimes, even just a phone call is a welcome change. I once called to say, “Hi, how are you?” with no other reason, no discipline, just a friendly chat about them, the truck driver. This can also show the driver that they’re valued and that the company’s management really cares about them. After all, if the wheels aren’t turning, a company isn’t making money.

Another way to keep your top talent is to invest in technology. Features like route optimization, Electronic Logging Devices (ELDs) and promoting a healthy work-life balance can really show drivers that they’re valued. It would be great to have a fleet of trucks that are relatively new for your drivers, but that’s becoming harder to do these days. The cost of a new truck is so high, and you need to keep it running to pay for it.

Another way to keep drivers happy is for managers to keep their word. If you create a workplace where drivers feel valued and heard, they’ll be more likely to share their concerns with you. When you promise to investigate something, like “I promise to look into that,” make sure you do. Check out the issue and then let the driver know what you’ve found. Some managers might not even investigate the problem, but I believe most do. It’s crucial to share the results with the driver so they know they’ve been heard and that you’ve taken steps to address the issue. Even if the outcome isn’t what they hoped for, at least they know you’ve acted. This really helps build trust and strong relationships.

I’d like to wrap up with a thought on ‘respecting the driver’s time!’ This is about ensuring you pay the driver for their time when they’re delayed beyond what’s fair. I’ve always wondered why trucking companies and truck drivers sometimes allow two hours or more for loading or unloading and not charge the client and pay the driver. If the shipper has given you a delivery time and you’re on schedule, why can’t they unload you in a reasonable amount of time? Truck driving is one of the few jobs I know where people give away their time, and it feels like a huge loss.

Looking ahead to 2026, I’m expecting things to stay pretty much the same. We’re in a recession, and I don’t think we’ll see any real improvement until the second half of the year. For companies aiming to keep their top talent, here’s a thought: talk to them and make them feel valued.

If you’re a driver on the hunt for a new job, make sure your resume is spotless and that you’re accident-free. The job market is competitive, so you’ll want to make sure you really shine.

Wishing you all a healthy and prosperous 2026!

Happy New Year!

Chris Harris
CEO & Top Dawg
Safety Dawg Inc.
905-973-7056
chris@safetydawg.com
@safety_dawg (twitter)