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How Do I Decode Software Deployments?

Jeff Bailey [Unofficial] May 13, 2026
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Prerequisites

This guide assumes:

  • Familiarity with Conway’s Law. Read What Is Conway’s Law? first if “communication structure shapes system structure” sounds new.
  • Access to the deployed system. You need to see the service list, runbooks, and on-call rotations.
  • Visibility into pipelines and release boundaries. You need to know which services ship together and which ship separately.
  • A blank document or whiteboard. You will sketch a map as you go.

Walk the deployment

Treat deployed software like a fossil record. Every service boundary, API contract, and deployment pipeline carries the imprint of the people who shipped it. Walk the deployment in this order:

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