In this episode of Generation AI, hosts Ardis Kadiu and JC Bonilla examine the widely misinterpreted MIT report claiming "95% of GenAI pilots fail," exploring why this headline misses the real story. While individual employees are finding significant value with AI tools (90% use personal AI regularly), organizations struggle to capture this value at the enterprise level—not because the technology doesn't work, but due to change management, leadership alignment, and implementation challenges. Through Element451's own QBR automation struggles, the hosts illustrate how the gap between impressive demos and measurable business impact stems from organizational readiness, not technological limitations. They discuss why vendor solutions succeed at twice the rate of internal builds (67% vs 33%), introduce Forward Deployed Engineers as the bridge between technology and business context, and explain why back office automation delivers higher ROI than marketing despite budget allocation. This conversation provides practical guidance for higher education leaders on moving from shadow AI productivity gains to true enterprise transformation, emphasizing that the challenge isn't whether AI works—it's how organizations need to evolve to capture its value.