“Don’t let the assholes win,” was Kelly Cooper’s advice to women in the trucking industry.

The human resources business partner at Loblaw Companies recounted how a safety supervisor’s husband doubted women could be truck drivers. Instead of backing down, she went and got an A/Z licence, she told the audience during Women’s Trucking Federation of Canada’s Bridging The Barriers conference in Mississauga, Ont.

Cooper said that people succeed when they are supported to pursue what drives them. The trucking industry, she argued, must create the conditions for that support, especially for women and underrepresented groups still facing systemic barriers.

She warned against treating diversity as a target to be announced rather than a process to be built. Declaring that 50% of leadership roles should be filled by women, for instance, means little without the planning, mentorship, and development needed to prepare people for those roles. “Change doesn’t happen overnight,” she said. Companies need structured approaches that identify and nurture talent well before promotions are on the table.

Kevin Jennings, transportation safety specialist at GFL, echoed the importance of deliberate planning, noting that his company has created the Women in Waste program to help women succeed in roles where they have been historically underrepresented.

Not a perfect environment

Driving a truck, he admitted, is not always the most welcoming profession, and the environment inside organizations is not always perfect either. GFL is working to close those gaps, but Jennings was candid about the tension between running an inclusive workplace and managing the day-to-day realities of a revenue-driven business. Balancing those pressures is difficult, but he argued that striving to improve every day is part of the job.

Representation in leadership matters not only for fairness, but also for retention, said Colleen Leonard, human resources operations manager at Polaris Transportation Group. When employees don’t see leaders who reflect their own experiences, they may assume their contributions are undervalued. The result can be turnover, often unnoticed until key people have already left.

Small gestures of support

Leonard said that that mentorship and role models, and even small gestures of support like telling an employee they are not alone or acknowledging a shared frustration can make workers feel seen and encourage them to stay engaged.

Systemic barriers often go unnoticed because they are woven into routine processes, noted Stephanie Carruth, founder of Minds for Matter. She pointed to something as simple as shift times. Operations may begin and end during hours that clash with school drop-offs or pickups, putting added strain on parents, most often mothers.

Other policies, such as rigid procedures for name changes, create unnecessary hurdles for employees who are transitioning. While changing a last name after marriage may be straightforward, she noted, transitioning employees often face multiple layers of paperwork and red tape.

Modest changes can have significant effects

For Carruth, these examples show why sponsorship and advocacy at all levels matter. Employees do not have to sit in leadership roles to push for improvements. Any staff member can raise questions about barriers and suggest ways to make workplaces more inclusive. Even modest changes can have significant effects on employee experience.

Cooper returned to the theme of allyship, explaining that being an ally is not only about speaking up but also about setting expectations for workplace behavior. She described Loblaw’s mandatory allyship training, which faced resistance from some employees who refused to participate. The company’s position was firm. While it may not be possible to change everyone’s personal views, it is possible to enforce respectful behavior in the workplace.

The importance of listening

Jennings added that effective mentorship begins with listening. He emphasized the need to hear employees’ concerns and management’s challenges in equal measure. Not every worker will be suited to every role, he admitted, but dismissing concerns without listening undermines trust and discourages participation.

Another practical tool, Cooper suggested, is job shadowing and ride-alongs. Dispatchers, supervisors, and even warehouse staff can gain valuable perspective by experiencing what truck drivers deal with on the road. Likewise, potential leaders can learn from shadowing managers in high-pressure moments, such as during holiday supply crunches.

Identifying untapped talent

These opportunities not only expose employees to different realities of the business but also help identify untapped talent. Workers may discover roles they had not previously considered, while leaders may gain new insights into frontline challenges.

The panel agreed that none of these measures are quick fixes. Meaningful change requires more than symbolic gestures or one-off initiatives. It involves careful planning, a willingness to adapt processes, and a commitment to mentorship and sponsorship across all levels of the organization.