Trust, Tech, and Talent: What Transportation and Infrastructure Leaders Are Missing

The latest KPMG Infrastructure and Transport CEO Outlook report isn’t full of surprising revelations – instead, it validates something I’ve felt to be true all along: the future of infrastructure and transportation leadership is fundamentally human. But while 62% of CEOs believe they need to step up and fill the trust void left by declining confidence in governments, many are still reaching for the old PR playbook instead of addressing the fundamental issues.

The Employer Brand Disconnect

Let’s be brutally honest: you can’t PR your way into being a trusted employer. This is especially true in transportation and logistics, where the day-to-day reality of work is far removed from the polished corporate messaging. Trust isn’t built through slick recruitment campaigns or values plastered on warehouse walls. It’s built from the inside out, through day-to-day experiences that either reinforce or contradict what you’re selling to the outside world. Here’s what I consistently see in transportation and logistics companies: very little investment in external employer branding overall (with the exception of driver recruiting) and even less investment in shaping internal cultural reality. When companies do show up, they’re often showcasing innovation and cutting-edge technology in their recruitment materials, but in actuality, their employees are struggling with outdated systems and rigid processes. They promise meaningful work and growth opportunities, but their current workforce is stuck in silos with unclear advancement paths. This disconnect isn’t just hypocritical – it’s expensive. When new hires experience the gap between promise and reality, they don’t stick around. And when theres no intention at all, it isn’t just a missed opportunity – it’s actively damaging. Without a clear focus on employee experience, people feel adrift, undervalued, and disconnected from any larger purpose. They’re left to navigate opaque systems and processes on their own, leading to frustration and disengagement. In an age of Glassdoor reviews and LinkedIn posts, word gets around fast about which companies invest in their people and which ones don’t. The cost? High turnover, difficulty attracting talent, and a workforce that’s just going through the motions rather than driving your business forward.

Rethinking Talent Attraction

The transportation and logistics sector is facing a perfect storm of talent challenges. There’s an aging workforce of experienced professionals heading toward retirement, creating critical succession planning gaps. Meanwhile, mid-career talent who could bridge the generational and technological divide are scarce. And perhaps most worryingly, the sector struggles mightily to attract young, tech-savvy talent who could help drive digital transformation. As KPMG’s Richard Threlfall notes, attracting these IT-savvy individuals is a crucial challenge – but I’d argue it’s just one piece of a more complex talent puzzle. Think about it: you have veteran employees with deep operational knowledge but perhaps less comfort with new technologies, a thin middle layer of potential successors, and a new generation of workers with different expectations and skills. This isn’t just about attraction or retention – it’s about building an organizational bridge between the industry’s past and its future. Here’s what’s not working:
  • Emphasizing stability and traditional benefits when young talent prioritizes growth and impact
  • Focusing on technical skills while underplaying the sector’s role in solving major societal challenges (like supply chain resilience and sustainability)
  • Maintaining rigid hierarchies when younger workers expect more autonomy and input
  • Treating talent groups as separate challenges rather than interconnected pieces
  • Focusing on knowledge transfer only at the point of retirement
  • Letting generational differences create operational silos
  • Viewing technology adoption as purely a training issue
Instead, try this:
  1. Showcase Real Impact: Don’t just talk about “meaningful work” – show exactly how your logistics operations or transportation systems are reshaping communities and addressing climate challenges. Young talent wants to see their work matter.
  2. Highlight Innovation Opportunities: Instead of just listing the technologies you use, demonstrate how new hires can drive innovation. Share specific examples of junior employees who’ve led technological improvements in your warehouse operations or route optimization systems.
  3. Rethink Work Models: While not every role can be remote in transportation and logistics, there’s room for flexibility. Can you offer hybrid schedules for planners and analysts? Project-based work? Four-day weeks with longer shifts?
  4. Create Clear Growth Paths: Map out explicit career trajectories that show potential for both technical and leadership growth. Show how someone can progress from operations to strategy, or from regional to global roles.
  5. Create Cross-Generational Teams: Build project teams that intentionally mix experience levels and skill sets.
  6. Modernize Knowledge Transfer: Develop digital repositories of operational knowledge that blend traditional practices with new technologies.
  7. Bridge the Cultural Divide: Help veteran leaders understand and adapt to new workforce expectations. Consider creating forums where different generations can openly discuss work style preferences.
  8. Rethink Traditional Structures: Consider rotational programs that expose staff to both operational and technological aspects, and /or the creation of “innovation teams” that mix experienced operators with technical experts. 

The Human Side of Tech Adoption

The report reveals that 57% of CEOs lack technical capabilities for AI implementation. But here’s what they’re missing: the problem isn’t just technical skills – it’s change management. I saw this firsthand recently with a company investing years and millions of dollars into rebuilding their internal operating system. The tragic part? Their own employees didn’t even understand why. This wasn’t just a communication failure – it was a fundamental disconnect between the technology investment and the people meant to benefit from it. When employees don’t understand the ‘why’ behind massive technological changes, they can’t see how it connects to their daily work or the company’s future. Without this context, even the most sophisticated technology becomes just another hurdle in their day, rather than a tool for improvement. No wonder so many digital transformation efforts fall flat. Here’s what actually works:
  1. Start with the Users
    • Map out who will be using the technology and how it will impact their daily work
    • Involve drivers, warehouse workers, and dispatchers in the implementation process
    • Identify and empower internal champions who can drive adoption
  2. Build Learning Into the Process
    • Create structured learning paths that go beyond basic training
    • Allow time for experimentation and mistakes
    • Recognize and reward early adopters and innovative uses
  3. Address Resistance Head-On
    • Acknowledge and validate concerns about job security and role changes
    • Be transparent about how technology will change workflows
    • Provide clear support mechanisms for struggling team members

Moving Forward

The transportation and logistics sector is at a crucial turning point, but it’s not the one most leaders think. While everyone’s talking about technological transformation, the real challenge is far more fundamental: it’s about intentionally bridging generational knowledge gaps, creating meaningful employee experiences, and ensuring technology investments actually serve the people using them. The organizations that will thrive aren’t necessarily those with:
  • The biggest technology budgets (though technology matters)
  • The most aggressive recruitment campaigns (though talent attraction is crucial)
  • The most elaborate training programs (though skills development is essential)
Instead, success will come to those who:
  • Take a clear-eyed look at their multi-generational workforce and intentionally create connections between institutional knowledge and new ways of working
  • Stop treating employee experience as an afterthought and start designing it with the same rigor they apply to operational processes
  • Ensure every technology investment starts with deep understanding of the people who’ll use it and clear communication about why it matters
Need help building these bridges in your organization? Let’s talk about where to start: leigh@glassballconsulting.com
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