Building better owner-operators: how fleets can support contractors for the long haul

May 7, 2025

Time to quit hauling someone else’s wagon.

I could make more running my own rig.

Why not be my own boss and keep the whole paycheck?

The dream of becoming an owner-operator still has pull—and for good reason. But when the excitement of independence meets the reality of business ownership, many drivers discover they weren’t as ready as they thought.

Many of them go bankrupt in their first year and that kind of instability hurts the driver, and it also poses risks for fleets. So, it’s in the best interest of the fleet to help those aspiring business owners succeed.

That was front and center in the March 2025 CarriersEdge webinar, Inside Training for Owner-Operators, where Mark Murrell and Jane Jazrawy shared what the industry's best performers are doing to help their contractors succeed—and what drivers need to understand before making the leap.

It used to be common to hear that training contractors wasn’t possible—but that’s no longer a valid excuse. While there are still legal considerations, enough fleets are doing it successfully that it’s become an industry expectation. Through tools like the CarriersEdge Owner-Operator Business Skills course and examples from Best Fleets to Drive For, we now have a clear roadmap for building stronger partnerships between fleets and their contractors.

Whether you’re a driver ready to take the next step, a new fleet still learning the ropes, or a seasoned carrier looking to support contractors better—this article lays out what works.

Mindset, money & mistakes: The real cost of going independent

Running a truck is not just a job. It’s a business. And the fleets that succeed with owner-operators are the ones that help reinforce that reality from the start.

As Murrell said in the webinar, If you treat [owner-operators] like company drivers, they’ll act like company drivers—and that doesn’t set them up for success.

It’s up to the fleets to guide aspiring contractors in the right direction—encouraging a mindset shift from company driver to independent business owner.

Successful contractors think like business owners. They plan, track, budget, and measure their performance. They know their fixed vs. variable costs. They make informed decisions about what loads to take, how to manage maintenance, and when to say no.

Fleets can support that shift by asking early questions like:

• What kind of business do you want to run?
• What are your monthly costs—beyond fuel?
• What do you want your career to look like in five years?

Helping drivers answer those questions doesn’t just protect their bottom line—it sets the tone for a stronger, more balanced relationship.

From dreams to data: Helping new owner-operators think like business owners

Fleets often focus on one group—either helping drivers transition into ownership or providing support to current contractors. The best programs do both.

New owner-operators need help understanding startup costs, tax structure, legal paperwork, and whether the owner-operator life is really what they want. The CarriersEdge course starts here, helping drivers prepare financially, emotionally, and operationally before they buy the truck.

Even experienced owner-operators still need support. Many lack financial systems, long-term planning, or a clear sense of how to stay profitable through market shifts. As Jazrawy pointed out, They don't realize they’re business owners. They act like company drivers with their own truck.

One fleet requires business plan reviews every three years. Another includes performance check-ins as part of quarterly coaching. That kind of consistent, non-intrusive support creates trust—and better outcomes.

The support stack: What the best fleets are doing right

The best fleets are building intentional, flexible programs that respect independence while reinforcing expectations.

What’s working:

• Onboarding business reviews: Some fleets now include financial conversations and goal-setting during orientation.
• Performance coaching: Regular reviews of miles, fuel, safety, and operating ratio—not as lectures, but as business reviews.
• Mentorship programs: Pairing newer owner-operators with more experienced peers or staff mentors.
• Access to resources: Some fleets offer structured business training or connect owner-operators with trusted legal, tax, or advisory services.

These aren’t mandatory trainings. They’re support systems. And the best fleets make them feel like tools, not rules.

No strings attached: Training without controlling the contractor

You can’t manage contractors like employees—but you can still set expectations.

The key? Focus on outcomes, not activities.

Instead of saying, You must take this course.

Try saying, Your contract requires a safety program. Here’s one we offer. Or bring your own—just make sure it meets these standards.

FedEx has been doing this at scale for years. Contractors are required to meet certain training requirements, but they can choose how. Most go with the fleet’s preferred vendors. It works because it’s flexible—and objective.

Incentives help, too. One fleet offers discounts on parts for owner-operators who complete optional training. Others tie perks to safety scores or on-time performance.

These are low-pressure ways to drive engagement and offer support—without overstepping legal lines. Be sure to consult legal counsel to ensure your approach aligns with current regulations.

Smart skills, safer roads: The surprising ROI of soft skills

Owner-operators need more than just driving skills—they need people skills.

Drivers—especially contractors—often don’t get training on how to manage people, negotiate with lenders, or navigate high-pressure conversations. But those are core skills for running a business.

Fleets are starting to offer optional training in:

• Leadership and communication
• Emotional intelligence
• Conflict resolution and negotiation

These aren’t touchy-feely extras. They help owner-operators secure financing, handle disputes, and reduce stress.

And stress matters. The more anxious a contractor is about money or uncertainty, the more risk they bring to the road. Predictability—financial and otherwise—is a safety tool.

More than miles: Why supporting contractors supports the whole fleet

Helping someone become a successful contractor isn’t just good for them—it’s good for your fleet. More stability leads to better safety, higher retention, and fewer surprise exits.

You don’t have to overhaul everything at once. Start by asking better questions. Build in coaching. Share resources. And keep the conversation going—through surveys, check-ins, or dedicated contractor groups.

Owner-operators aren’t just drivers with a different pay structure. They’re business partners. Treating them that way leads to better outcomes for everyone.

Want more practical strategies? The CarriersEdge Owner-Operator Business Skills course gives you tools to turn contractors into long-term partners—from day one.