Leading from the back: How people-first leaders drive performance
Key takeaways
- Strong leadership in trucking puts people first and creates an environment where employees can find purpose and fulfillment.
- Frequent, open communication helps teams understand goals, provide feedback, and see the reasoning behind decisions.
- Leaders build trust by giving employees autonomy, room to learn from mistakes, and support when they need it.
- Hiring for shared values and setting clear expectations help establish a culture where employees can succeed.
Management, decision-making, and leadership look different for every trucking company. Large enterprise fleets might have leaders who wear many hats, and smaller mom-and-pop operations—which make up 95% of trucking—most definitely have leaders who resemble a hat rack.
Transportation leaders manage assets and people. They read the spreadsheets and make the tough decisions. Truthfully, anyone can be a manager; however, not every manager is an influential leader.
FleetOwner spoke with a few of the industry’s influential leaders to understand what it takes to inspire others and drive positive change. These leaders, regardless of where they work or the differences in their operations, share a few traits.
Fleet success starts with a people-centric culture
Leaders can't lead without people, and trucking is a people business. That’s what Ken Roemer, president of PacLease, told FleetOwner. It’s a sentiment you’ll hear from most people in this industry. And while Roemer was referring to doing business, Ron Flanary, SVP of operations at Southern Glazer’s, refers to the business as people-centric when running a business.
Flanary believes everyone should feel fulfilled, and they should be happy. And because they spend 40 or more hours a week at their workplace, “as senior leaders, it's incumbent on us to create that environment where at least we give them the opportunity to be fulfilled and happy."
How can a leader help others feel fulfilled and happy? Having a conversation helps.
Establish open two-way communication across the fleet
A recent FleetOwner feature, “Beyond the truck number,” which covered what truck drivers want, highlighted something management should always provide: thorough communication.
Flanary skips memos and long emails. Instead, he has regular, in-depth conversations with his team members. “They all know exactly what we're trying to accomplish and what our big, meaty goals are, and the way that we're going to behave as an organization and as a leadership group to get there,” Flanary said.
To Roemer, communication can never be exhausted. “I’ve always believed you can’t communicate too much,” he told FleetOwner. “That goes for our employees, our leaders, our dealer network, and our customers."
Communication should stretch throughout the team in the office and the team outside the office. Flanary said Southern Glazer’s keeps an open communication loop with its drivers because, unlike office and warehouse staff, drivers are out on the road talking with customers, dealing with routing changes, and more.
“We have a feedback model with our drivers where they can give feedback to the routing team and to the leadership team every day based on what they saw,” Flanary said.
Communication helps teams get on the same page, but it also helps team members understand the “why” behind management’s decisions. “If you want people to really get behind a decision, you have to explain the thinking behind it. When people understand the ‘why,’ they’re a lot more likely to buy in and move forward with you,” Roemer said.
Embrace servant leadership to build operational trust
Both gentlemen said explaining decisions and working with employees instead of barking orders is now the more effective leadership style.
“The old approach of just giving orders and expecting everyone to fall in line doesn’t really work anymore,” Roemer said. "Instead, people appreciate transparency and context. This builds trust.”
Similarly, Flanary believes that servant leadership is more effective.
“There's this command and control [leadership style] that has its place … where the leader is at the top, and he is at the front of the room,” Flanary said. “Well, that doesn't really work every day. … Then you’ve got servant leadership.”
Flanary serves his team by “sliding into the background” and letting his team members shine in their roles. This means giving them room to thrive, or giving them “oxygen,” as he explained. It also means giving them space to make a few mistakes, since mistakes result in lessons learned. And every leader needs a few battle scars, he said.
Roemer has a similar approach: Hire good people, and let them perform. “I’ve learned that if I feel the need to micromanage someone, I probably missed something in the hiring process,” he said.
Like Flanary, Roemer said a leader’s role isn’t to stand over team members; it’s to provide them the tools they need to succeed. And though Flanary said he often stands in the back of the room, his staff knows he’s always there to support them.
Delphia Howze speaks on leadership at the Women in Trucking Accelerate conference
skilled trades shortageEquip drivers and frontline teams with tools to succeed
Influential leaders understand that when their team succeeds, they succeed. That’s why Roemer and Flanary put their team first.
Roemer’s leadership formula is simple: “Remove obstacles, provide support, and give [team members] the space to succeed.”
That will look different for every company. For Flanary, it means providing his drivers with reliable, safe, and well-maintained equipment. He also ensures the route they’re given is one that will lead to success—whether it involves more optimization or a route with customers with which they already have relationships.
“You have to lay the foundation for them to be successful, and then you have to create the culture where they know what's expected,” Flanary explained.
That culture begins during the hiring process.
Recruit for cultural fit: Hiring for attitude over aptitude
Fitting within a company’s culture—or even a team’s culture within the company—is vital for employee success. This doesn’t mean that employees leave their individuality at the door; rather, it just ensures that employees share the same values, work ethic, and goals as the company. Knowing whether a prospective employee will fit into the culture means considering it from the beginning.
Fortunately, culture can be built and even changed, if needed. Flanary created a culture that puts the employee first. “I'm going to have the type of environment, and I'm going to have the type of culture that's going to get [employees] ready for the next level,” he said. “So, you make it about them.”
Find what employees want out of their careers and help them achieve that goal. You can determine goals before team members are hired.
Leaders recognize how vital the hiring process is, and Roemer, Flanary, and others confirm this. Whether you believe in the power of first impressions, it’s those key moments when leaders can determine if the prospective employee will add to the culture or infect it.
“Hire for attitude, not aptitude,” Shari Pheasant, a repair shop owner and one of FleetOwner’s 2026 Women in Transportation, said earlier this year. She means anyone can be taught a skill, but it’s only those who want to learn that will learn.
If employees become unhappy, that attitude can change and wreak havoc. “When you fire, you fire for attitude,” Pheasant said, “because the attitude affected the aptitude.”
Attitude affects aptitude, and it can disrupt the culture that’s been established through years of history, such as with PacLease.
“We’ve been in business for 46 years, and we’re proud to be part of Paccar’s 121-year legacy,” Roemer said. “That history matters because it’s rooted in values such as quality, innovation, integrity, and operational excellence. Those are the principles that have helped Paccar stand strong for more than a century, and they’re the same values we work to carry forward every day at PacLease.”
To ensure his employees share those goals, Roemer sets expectations from the beginning so each employee knows how their role plays into the company’s “bigger picture.”
“When employees understand their purpose and the value they bring, the culture you want starts to show up naturally throughout the organization,” he said.
Prioritize active listening and continuous industry education
“I’m always learning,” Ron Flanary told FleetOwner. “I read a lot.”
“The trucking industry is always evolving, so as a leader, you have to stay on top of emerging trends, new ideas, and what your customers need,” Ken Roemer said.
“I listen to podcasts every single day—that’s what I do with my commute time,” Amy Hudson, chief operations officer at Mike Albert Solutions and 2025 Woman in Transportation, told FleetOwner last year. “If I can [learn] something on my drive in the morning and my drive home at night—winner!”
A successful leader is an informed leader. And the three leaders those quotes belong to have mountains of success within their tenure.
The desire to become well-informed boils down to a leader’s desire to grow their skills and understand what’s happening in the market to support decision-making. A leader who believes they already know everything risks making a decision without the best insight available from an expert or a team member; they also risk treating their employees as burdens rather than helpers.
In other words, leaders who understand they don’t know everything practice humility—a key requirement for effective leadership, according to Flanary.
“If you think you already know the answers, then you really don't need everybody else on your team, and then they don't develop, and they don't grow,” Flanary said.
Roemer ensures he’s asking all the questions—especially the tough ones. This helps him learn, but it also helps him build stronger relationships and, in turn, become a better leader.
Listening informs decision-making, but it also helps leaders understand the needs of their team members and helps leaders provide better support and tools for the job—essentially creating the full circle of leader/employee relationships.
“One of my mentors told me very early in my career … that you can never really be successful if the only person you're worried about is yourself,” Flanary said. He works “tirelessly” to make his team, boss, and company successful, because at the end of the day, that fuels his success. “It's going to come back to me, but I shouldn't be the primary focus.”
About the Author
Jade BrasherJade Brasher
Executive Editor Jade Brasher has covered vocational trucking and fleets since 2018. A graduate of The University of Alabama with a degree in journalism, Jade enjoys telling stories about the people behind the wheel and the intricate processes of the ever-evolving trucking industry.
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