DOP 342: Your Company Documentation Is Useless for AI

2026-03-18

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#342: Most companies have plenty of documentation. The problem is almost none of it is findable, current, or true. Between what's documented, what's actually true, and what people actually do, there are gaps wide enough to kill any AI initiative before it starts. Viktor makes a distinction that reframes the whole problem: there are two types of documentation. Why something was done -- that's eternal. How something works -- that's outdated the moment someone changes a config and forgets to update the wiki. The...

Viktor makes a distinction that reframes the whole problem: there are two types of documentation. Why something was done -- that's eternal. How something works -- that's outdated the moment someone changes a config and forgets to update the wiki. The information about that change probably exists somewhere -- in a Zoom recording, a Slack thread, somebody's head -- but it's not where anyone would think to look for it.

The running system itself is the most accurate documentation any company has. Your Kubernetes cluster tells you how many pods are running right now. Git tells you how many you wished you had. Those aren't the same thing, and pretending Git is the source of truth is a comfortable lie most teams tell themselves daily.

RAG won't save this. Not the way most people imagine it -- point an agent at your docs and let it answer questions. That fails for the same reason Google's old enterprise search appliance failed. What could work is a continuous process that watches every information source, extracts what matters, and updates a central location intelligently. We have the pieces for this. Nobody's built it yet.

The practical path forward: audit what you have before building anything new. Instrument your documentation the way you instrument applications -- find out what people search for and can't find. Design for retrieval, not storage. Build feedback loops. And stop treating documentation as a project with an end date. The companies that treat this as a strategic advantage instead of a chore are the ones that will actually make AI work for them.

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