Is There a Formula for Best Fleets Success?

Published on June 17, 2026

Every year, carriers participating in the Best Fleets to Drive For program ask some version of the same question: Is there a formula for success?

After all, if one company finds a winning approach, shouldn’t another be able to follow the same roadmap and achieve similar results? The answer, according to Andrew Winkler, general manager of Chief Carriers, is more nuanced than that.

During a session at the 2026 Best Fleets to Drive For Conference, Winkler, who is the only person in the history of the Best Fleets to Drive For program to help two different trucking companies earn Best Overall Fleet honors, explained his approach and success in the program.

“There is no universal checklist that guarantees a fleet will become a Best Fleets winner,” said Winkler. “Every carrier has different drivers, freight they haul, challenges, and culture. What programs work well for a reefer fleet may not resonate with a flatbed operation. What motivates one driver population may have little impact on another.”

Before joining Chief Carriers, Winkler spent more than two decades at Grand Island Express, where the company became a Best Fleets Hall of Fame member and won multiple overall awards. Since arriving at Chief Carriers in 2018, he has helped transform the company into a six-time Best Fleet and Best Overall Fleet winner in the small carrier category.

While he believes there isn’t a specific ‘Best Fleets’ formula fleets can look to copy to become an award winner, he said there are repeatable processes fleets can put in place to analyze the key principles that consistently create winning cultures.

Start With Trust

While many companies focus on benefits, technology, or new programs when trying to improve driver satisfaction, they rarely work unless drivers believe leadership is truly listening. According to Winkler, trust is built when fleets address issues drivers care about, communicate openly, and follow through on commitments. Drivers don't need leadership to solve every problem overnight; they need evidence that their concerns are being heard and acted upon. For driver’s “show me the money” means more than a paycheck. It means show me you care.

For example, when Winkler joined Chief Carriers, one of his first observations involved flatbed drivers securing and tarping loads in harsh Nebraska weather. After seeing the physical demands of the work firsthand, he more than understood that drivers weren't being paid as they should. So, he approached company leadership about increasing activity pay related to those tasks. They agreed and made changes…it showed leadership was listening.

Soon after, Chief Carriers also invested in climate-controlled securement bays where drivers could secure loads out of the weather. The project addressed a practical concern that drivers faced every day, and helped Winkler further establish creditability with drivers that he was looking out for ways that could improve their experience on the job.

Focus on a Few Things and Do Them Well

When fleets receive their Best Fleets benchmarking reports, there can be a temptation to identify dozens of areas they would like to improve and attempt to tackle everything at once. But is that realistic?

Instead of launching dozens of initiatives simultaneously, Winkler said he focuses on one or two major priorities each year. By having a disciplined approach, it can allow organizations to make meaningful progress without overwhelming employees or drivers. Incremental improvement compounds over time. Organizations that focus their efforts on key issues or opportunities are more likely to create lasting change than those constantly chasing new initiatives.

According to Winkler, when fleets assign a person or group to spearhead the company’s involvement in the Best Fleets program, but that person lacks the authority to advocate or make changes, it can limit the program’s value. The most successful fleets typically have a leader involved who not only understands the organization's goals but also has enough influence to drive action. Improvements happen when someone is accountable for turning insights into results.

Communicate What Programs Are Already Available

Winkler also believes that one of the biggest missed opportunities fleets have is a lack of communication with drivers about what programs or benefits are already available to them. Out of sight, out of mind – fleets often do more for drivers than drivers realize. The challenge isn't always creating better programs; its helping drivers understand what already exists.

Winning fleets consistently communicate their story about what they’re doing to prioritize drivers and how they’re striving to continue to be better. They explain why decisions are made, share company goals, provide transparency around challenges, and create opportunities for feedback.

Sometimes a simple policy adjustment, or improved explanation of an existing benefit can significantly improve the employee experience. When consistent communication practices and an open dialogue with drivers are in place, drivers will develop a clearer understanding of the organization and a stronger sense of connection to it.

Ultimately, what works for one fleet may not work for another. Different driver populations value different things. Different business models create different challenges. Benchmarking your fleet with other successful companies in the Best Fleets program is still a great starting point but basing your decision solely off that won’t guarantee your own success. When making decisions to improve the driver experience, being consistent in listening to your drivers and understanding their challenges and needs and communicating to them that they’re being heard is the foundation for a successful driver culture. That’s what moves the needle and can help set you up for success.