SREday

Site Reliability, DevOps and Cloud

June 6, 2026 Datadog, New York, US

1
Day
10+
Speakers
2
Tracks
80+
Attendees

Your Outdated Docs are Costly: Why You should be writing tests for your docs

Omari Gaskins Jr
DocuSOR
Abstract

Internal Developer Platforms aim to create golden paths, reduce cognitive load, and standardize how teams build and operate software. But there’s a blind spot: documentation. READMEs, onboarding guides, and operational runbooks are often treated as static artifacts. Over time they drift from reality, even as the platform itself evolves. The result is slower onboarding, brittle self-service workflows, and increased support burden on platform teams. In this talk, I’ll explore documentation as an unverified surface within Internal Developer Platforms, and introduce a practical approach to making it executable. By treating markdown instructions and runbooks as workflows that can be executed and validated inside CI or ephemeral environments, platform teams can detect drift automatically. Setup steps, service bootstrapping commands, and health checks become verifiable contracts rather than informal guidance. We’ll cover: • Why documentation drift increases cognitive load and support tickets • How to integrate executable documentation into platform pipelines • How this approach strengthens golden paths and reduces onboarding time • What changes in platform team workflows when documentation becomes testable Document drift is a universal problem, and a costly one. It's time we implmented an actual fix.

Bio

Omari Gaskins Jr. is the creator of DocuSOR, the first platform that executes and validates documentation to prevent drift and accelerate developer onboarding. As a Software Engineer at JPMorgan Chase for the last 5 years, he has worked on hundreds of different applications, with on prem and public cloud integrations, managing the scale that comes with working for a large global enterprise.

Video

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