JD Dillon

We’ve never had more information. More tools. More ways to connect. And yet people feel more disconnected, disengaged, and lonely at work than ever before. What’s going wrong? 404: Leadership in the Age of AI explores the tension organizations face as work becomes increasingly shaped by intelligent systems. In pursuit of a frictionless workplace, we risk losing the moments that make work human — the times when we rely on one another, build trust, and find meaning in something bigger than ourselves. As AI reshapes how work gets done, leaders have a critical role to play in preserving purpose, connection, and humanity at work. I challenge organizations to elevate the people side of work as they pursue efficiency and profitability. First, they must provide leaders with the clarity, skills, and space needed to build community while applying technology with purpose, so progress does not come at the cost of meaning. When AI becomes the standard, connection becomes the only true differentiator.

We see them every day. Behind counters. On delivery routes. In hotel hallways and hospital rooms. Yet the people who keep our organizations running are often left out of conversations shaping the future of work. The (In)visible Workforce explores the gap between seeing deskless workers and truly understanding their reality. Drawing on stories from the frontline workplace, I share lessons in courage, resilience, and connection from people who navigate constant change and demanding conditions while showing up with pride and purpose every shift. Leaders have an opportunity to shift from awareness to action by rethinking how work is designed, supported, and led on the frontline. Together, we can foster stronger performance, measurable outcomes, and a more equitable work experience, built for the grocery clerks, healthcare workers, restaurant servers, and tradespeople we rely on to get the job done.

Why didn't it work? You had the strategy. The technology. The budget. The implementation plan. The executive sponsorship. All signs pointed toward success. Yet somehow adoption stalled. Employees found workarounds. Managers struggled to keep up. Old habits persisted. The promised results never materialized. This happens time and time again with business transformation efforts - from AI adoption and digital modernization to safety initiatives and customer experience programs. Organizations invest enormous time and resources designing the future while overlooking the employees expected to make it a reality. They spend months planning the change and only minutes considering the people side of transformation. The result is a costly gap between strategy and execution. Change Happens Here explores why lasting business transformation requires more than technology, process, and planning. Drawing on lessons from frontline workplaces around the world, I reveal what drives people to embrace new ways of working, why resistance often signals deeper issues, and how leaders can create the trust, clarity, and support employees need to move forward with confidence. Plans don't drive change. People do.