ReadyCIO · Getting your organization ready for AI
CEOs, how robust is your AI plan?
Most companies have something they call an AI plan: licences for everyone, a policy email, an app someone built over a weekend. Few have one that would survive a bad week. ReadyCIO is a working engineer's notebook on getting an organization genuinely ready for AI: what a robust plan contains, what has to surround the apps, and how the lessons get kept. Written for the people deciding first, and for the people building alongside them.
I run a company
Test your AI plan against a bad week.
Twelve questions a leadership team can answer in one meeting, and the homework to require before relying on anything an employee builds.
Start here →I build with AI inside a company
The informed way to code with AI.
The five questions your company will ask of AI-written code, whether you started last week or last year, and how to answer them.
Start here →Working out right now
- Can a company measure whether its AI licences did anything?
- What should a company require before relying on an app an employee built?
- What does a company keep when the person who built it leaves?
- Is a quarterly security pass enough for software built weekly?
Each one links to where it is being worked out. The board changes when the questions do.
What you learn about AI is worth more than the tool.
Every team learns the same lessons about working with AI and forgets them by the next session, the next project, the next person. A vault fixes that: lessons written once, applied automatically in every session, kept true by audits and a rule for contradictions.
It is the one part of an AI plan I would start with if I could only do one. The learning loop →
Latest notes
All notes →-
Sep 11, 2026 For companies
AI writes instant legacy code
Code written with AI is being thrown away or rewritten within weeks at twice the old rate, and the share of code being refactored is falling. The draft is faster. Owning it is not.
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Sep 11, 2026 For companies
Fast food architecture
AI is a very good drafter and a poor architect. Treating its output as finished engineering is like living on fast food: it works today and costs you later. The fix is a place the reasoning lives that the model can read back.
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Sep 11, 2026 For companies
The build is the cheap part
A tool built in 48 hours feels free until the first API change. The initial build was always the small share of the cost of owning software, and AI just made that share smaller.
Playbooks
All →- The infrastructure around the app
A homework checklist for anyone building an application a business will rely on, and for the leader deciding whether to let them. The app is the easy part; this is everything else.
- What an AI plan actually contains
Five short things with owners, not a fifty-page strategy. The plan for a company of ten to two hundred people, what each part is, how long it takes, and the order to do them in.
- Reviewing code you did not write
The review pass I run on everything an AI coding tool produces: what to read first, the mistakes that show up most, tests as the contract, and how to keep context so the next session does not repeat the last.
- Finding where AI actually pays off in a small business
A two-week method for working out where software or AI would save real time or money in a business of ten to two hundred people: map the workflows, score by payoff and effort, check readiness, write it up so the owner can act.
Who writes this, and why the name
Ready, as in ready for AI. CIO, as in the perspective of the person responsible for making it work. Darren, software engineer and technology lead. I work full time for an employer and write here in my own time; the views are mine, this is not a consultancy, and I am not taking on client work. If something here is useful, connect on LinkedIn and tell me what you are building. More →