There is no shortage of articles telling you what RAG is.
This is not one of them.
This is what happens when you actually build one — over real content, with real questions, and an honest evaluation of what works and what does not.
What Is RAG and Why Should You Care?
RAG stands for Retrieval Augmented Generation.
The idea is simple. Before answering your question, the AI searches your documents, finds the most relevant pieces, and uses those to construct a grounded answer — not a generic one.
Think of it as the difference between asking a colleague who has read your internal policy documents versus asking someone who has only read the internet.
Most enterprise AI assistants being deployed right now use this approach. Internal knowledge bots, policy assistants, code documentation tools — RAG is underneath most of them.
What I Built
I wanted to understand what enterprises actually face when they deploy these systems. The only honest way to do that was to build one myself and stress-test it.
So I built a RAG system over 14 years of my own content — 111 blog posts from agilebuddha.in and my book on Agile estimation. Then I ran real questions against it and documented every failure.
The technology itself took eight focused sessions of 60-90 minutes each. It is not rocket science.
What came after building it — that is where it gets interesting.
What I Found
[Read more…] about 14 Years of Writing. One AI System. Here’s What It Found.
