RENO, Nev. — Every decision a transportation leader makes reaches far beyond the issue at hand, explained Keba Baldwin, the transportation director for Prince George’s County Public Schools in Maryland.
Whether changing a bus route, implementing new technology or making a difficult staffing decision, leaders must consider how those choices affect employees, students, families, and district operations.
During his session Sunday at STN EXPO West conference, Baldwin, the reigning STN Transportation Director of the Year, encouraged transportation professionals to move beyond simply solving immediate problems and instead develop leadership habits that strengthen their organizations over the long term. Drawing on his experience leading one of the nation’s largest school transportation operations, Baldwin outlined several leadership traits that he believes can help directors navigate increasingly complex school transportation environments.
“Our goal for today is just to really understand the decisions that shape your daily operations and the long-term success that you’re looking for,” Baldwin told attendees on Sunday. “Leave out of here with a better understanding, a better playbook of how to do that.”
Baldwin oversees transportation for approximately 85,000 students at PGCPS, which serves roughly 130,000 students outside Washington, D.C. His department includes about 1,400 employees, a fleet of 1,200 school buses and approximately 800 support vehicles. He told attendees that working in transportation departments ranging from 60 buses to one of the nation’s largest fleets has reinforced one lesson throughout his career: Operational challenges rarely disappear as organizations grow. Instead, leaders must learn to adapt their decision-making to increasingly complex systems and larger teams.
“The issues are the same,” he said. “It’s basically how do you scale them up.”
Looking Beyond the Immediate Problem
One of Baldwin’s primary messages centered on what he called “system awareness,” or understanding the ripple effect every decision creates throughout a transportation department. A seemingly simple routing adjustment, he explained, can influence staffing levels, communications with families, training needs and overall public confidence in the transportation system.
“Every decision in your transportation department has a ripple effect,” Baldwin said. “A routing change touches staffing. Your staffing shortage becomes a communication problem. A procurement decision reshapes training. Your technology rollout moves a family’s confidence up or down.”
He cautioned that transportation leaders who focus only on solving the immediate issue are more likely to experience burnout and unintended consequences later.
“The director who only sees that first order is going to get burned out very quick. You have to be able to see it all the way through. You’ve got to play the second, third, fourth order,” he said.
Baldwin illustrated the concept using his school district’s summer transportation planning process. Extended School Year transportation depends on multiple departments meeting tight timelines, while route bidding, dry runs and parent communications all must occur within a condensed schedule. Delays in one department can quickly disrupt transportation’s ability to deliver services.
Baldwin said that same deliberate approach should apply to procurement decisions, which often involve transportation, finance and purchasing departments working together. Rather than rushing contracts or major purchases, he encouraged leaders to understand district procurement processes, carefully review contract language, and build relationships with purchasing and budget officials. Doing so, he said, can help departments avoid costly mistakes while positioning them to take advantage of funding opportunities when they arise.
Building Trust on the Front Lines
Beyond managing budgets and contracts, Baldwin said transportation leaders must remain connected to the people who keep their operations running.
He argued that many administrators describe drivers as “the backbone of the operation,” but said genuine appreciation is demonstrated by spending time alongside frontline employees rather than simply acknowledging their contributions.
Baldwin challenged attendees to consider how often they make themselves visible in the field. “How often are you at your bus depot? How often do you ride a bus?” he asked.
He said regularly riding routes and visiting bus depots allows transportation leaders to better understand the daily challenges drivers face while building trust throughout the department.
“How often do you just show up at a bus depot and get on a bus with a random driver and ride their route?” Baldwin said. “Do you know if you do that, how much clout you will gain? … They’ll see you not so much as a person that sits behind a desk, but rather than a person who understands what they go through.”
Baldwin added that leaders should focus on coaching employees rather than viewing every interaction as a disciplinary conversation, emphasizing the importance of treating staff members with respect while helping them improve.
Strategic Leadership and AI
Baldwin also emphasized the importance of establishing clear expectations throughout an organization.
He encouraged transportation departments to develop strategic plans, mission statements and operational goals that remain visible throughout the year rather than becoming documents that are referenced only during evaluations.
“You’ve got to have your mission, your vision and objectives,” Baldwin said. “People need to know what you’re about when they walk through the door.”
He said those expectations should become part of a department’s daily culture, giving employees a shared understanding of the organization’s priorities and creating accountability among coworkers rather than relying solely on supervisors.
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For districts looking to improve efficiency, Baldwin encouraged transportation leaders to embrace artificial intelligence instead of avoiding it.
He said AI has become a valuable tool for drafting communications, analyzing transportation data, updating standard operating procedures, and identifying employee retention strategies.
“We’ve learned to embrace it,” Baldwin said. “Don’t shy away from it. Take it and use it to your advantage.”
In his department, AI has significantly reduced the time required to analyze operational data, allowing staff to produce reports for school board members and district leaders much more quickly than before.
Baldwin said the technology has also helped his team draft standard operating procedures, update employee handbooks and identify workforce trends that can guide recruitment and retention efforts. While AI can improve efficiency, he encouraged attendees to verify the information it produces before incorporating it into operational decisions.
As the session concluded, Baldwin encouraged attendees to continue learning from one another and strengthening the relationships they build across the profession, noting that collaboration is one of the industry’s greatest assets.
He reminded transportation professionals that the work they do carries tremendous responsibility and encouraged them to recognize the value of their contributions while supporting one another.
Article written with the assistance of AI.
