Episode 34: Stories of Digital Transformation Failures feat. Barry Flack

Hear Barry Flack, Fractional HR Executive and HR tech advisor, explain why roughly 70% of digital transformation projects fail on culture, not technology.

Most digital transformation failures aren't about the technology. They're about the people nobody planned for. In this episode of The Team Check-In, host Emre Ok talks with Barry Flack, a Fractional HR Executive and HR tech advisor with three decades of experience guiding organizations through change, about why roughly 70% of digital and AI projects fail once you look past the rollout plan.

Barry walks through the global ticketing system that cost a fortune and got quietly abandoned because it ignored local relationships, and the recruitment tool that solved one problem by creating a flood of bot applications. He also explains the two things every organization has to accept are unpredictable, and what separates organizations that make technology stick from the ones stuck replacing failed rollouts every few years.

Chapters

  1. 05:20 What "culture eats AI for breakfast" actually means
  2. 07:17 Why 42% of businesses scrap their AI initiatives
  3. 16:38 The ticketing system that killed local relationships
  4. 25:09 Complexity: the two things you can never predict
  5. 30:03 What organizations that get it right actually do
  6. 38:26 Easy Apply: when fixing one problem creates a bigger one
  7. 41:05 Where AI actually delivers value in HR
  8. 46:15 Is your tech making people lonelier?

Key Takeaways

  • Technology gets the blame; culture is usually the real cause. Barry says roughly 70% of digital and AI projects fail not because the tech is bad, but because organizations never address the cultural and adoption side.
  • A restrictive rollout can cost more than it saves. An 18-month global ticketing system backfired because people kept working around it through local relationships instead, and the technology took the blame for a problem it didn't create.
  • Fixing one problem can create a bigger one. The recruiting feature "Easy Apply" solved for applicant convenience, then got flooded by bots and overwhelmed the same talent acquisition teams it was meant to help.
  • Two things are always unpredictable: people and the market. Barry argues that accepting this complexity, instead of engineering it away with a Gantt chart, is what separates organizations that adapt from the ones repeating the same rollout mistakes.
  • Successful organizations promise technology won't replace people, then act like it. He points to decentralized organizations that give people time and space to make decisions and frame new tools as help rather than a threat.
  • Ask whether your tools are making people lonelier. Barry cites data showing the top predictor of employee retention is having a best friend at work, and warns that always-on AI tools can end up substituting for the messy human connection that actually keeps people around.

Speakers
Emre Ok
Product Marketing Manager
Teamflect
Barry Flack
Fractional HR
B F Consultancy