Modern CTO Why AI Is Stalling in the Enterprise, and How Leaders Can Fix It with Greg Shewmaker, CEO at r.Potential
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Sep 8, 2025 In this conversation with Greg Shewmaker, CEO of r.Potential, they dive into why AI projects in enterprises often falter. Greg emphasizes the importance of having a clear vision that goes beyond technology, reshaping leadership and decision-making. He shares insights on the challenges of AI adoption in larger organizations and the significance of fostering meaningful human connections amid automation. The discussion also touches on redefining wealth and the need for purposeful work in an AI-driven world.
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Treat AI As Accountable Co‑Workers
- Greg Shewmaker frames AI as a co-worker that must be onboarded, tested, and held accountable like human colleagues.
- He argues AI should be built purposely to support specific humans, not replace them wholesale.
Fear Is Driving Failed AI Adoption
- Greg observes most enterprise AI projects fail to deliver ROI and warns adoption is driven by fear rather than strategy.
- He says leaders skip hard questions about competitive impact and organizational change, causing pilots to stall.
Sequence Strategy Before Deployment
- Assess how AI changes your competitive landscape before deploying tools inside the company.
- Then determine organizational responses and only after that redesign work and roles.