Field Guide / Free
The Pragmatic AI Migration Playbook
A working playbook for moving from individual AI experimentation to organization-wide capability. The maturity model, the four migration tracks, the governance discipline, and a 90-day execution plan. Read it in an evening. Use it for a year.
Most organizations are stuck at the same place with AI: individuals are productive, the organization is not. People build their own prompts, their own workflows, their own context. Productivity compounds for them. Capability does not compound for the team.
The Playbook is the framework I use when an organization decides to change that. It's the same framework behind the Pragmatic AI Migration essay, expanded into a working guide your team can actually execute against. It's also the methodology behind the Operations AI Engagement — published in full so you can decide whether your team can run it on its own.
Eight chapters. No vendor lock-in, no platform pitch, no five-year consulting roadmap. Read it in an evening, work it for a quarter, revisit it as the team matures.
Table of contents
Eight chapters
- 01
The Organizational Gap
Why personal AI works, why organizational AI stalls, and why nobody on your team is talking about the actual reason.
- 02
The Five Levels of Organizational AI Maturity
A diagnostic ladder, adapted from automation-maturity thinking, that gives your team a common vocabulary for the conversation it is probably not having.
- 03
Track 1: Process Encoding
Capturing how your organization actually works in a form an AI can follow. The fastest-payback move in the entire Playbook, and the one most teams skip.
- 04
Track 2: Knowledge Architecture
If process encoding tells agents how to do things, knowledge architecture tells them what exists and how it relates. Most companies have neither, and have not noticed.
- 05
Track 3: Governance
The unglamorous discipline that keeps encoded processes and knowledge architectures from rotting. Skip this and your AI investment turns into technical debt within a quarter.
- 06
Track 4: Progressive Automation
Moving workflows up the autonomy stack — augmentation first, autonomy where it has been earned. The wrong order produces confident wrongness at industrial scale.
- 07
The Compounding Effect
Why the gap between a Level 1 organization and a Level 3 organization is not linear, and why it gets harder to close every quarter.
- 08
The 90-Day Plan
A concrete, week-by-week execution sequence to take an organization from Level 1 to a foothold at Level 2 — and the discipline to keep going from there.
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