As technology leaders, our most critical job is understanding the actual architecture of the tools we buy. If we evaluate probabilistic AI models using the same procurement mindset we use for enterprise software, we expose our organizations to catastrophic, invisible risks. I looked at the recent DoD/Anthropic negotiations as a case study in how dangerous this category error can be.

(Read, The Room Where It Gets Built — Essay #8: LLMs Are Not Shelf-Stable Products)