The Real Reason Hybrid, AI, and Change Initiatives Keep Failing (with Brian Elliott)

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Leadership and management
Flexibility at work
Generative AI
Technology Adoption

David Green and Brian Elliott discuss why hybrid work and AI initiatives fail due to policy-driven approaches rather than outcomes-based thinking. He argues that trust issues and command-and-control leadership undermine flexibility initiatives, while measuring activity instead of results prevents meaningful transformation. Successful organizations redesign workflows, embrace team-based accountability, and coordinate IT, HR, and workplace functions. Elliott emphasizes that AI adoption parallels hybrid work challenges—both require rethinking how work happens, not just implementing new tools. The key is balancing business efficiency with employee enablement, reducing toil, and creating space for experimentation while avoiding burnout through measured implementation.

  • Hybrid work leadership
  • AI transformation challenges
  • Outcomes-based management approaches
  • Trust and accountability
  • Change management barriers
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