Cup of Wit

Cup of Wit

AI strategy for leaders who hate buzzwords

Published weekly. Free to read.

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Most AI content is written by people selling something.

This is written from inside a large organisation — where AI has to survive governance, budgets, and real constraints.

Strategy & Operating Models

AI that fits your org, not just the demo

Prompting & Context

Getting better outputs without the guesswork

Build Logs

Honest accounts of building with AI

Featured Writing

AI Does Not Replace Human Judgment — It Reveals Its Absence

For leaders who believe their organizations are ready for AI — and haven't asked what they're actually ready for.

How to Talk to AI Like a Manager, Not a Search Engine

Most people treat AI like a search engine. Managers assign. That mental shift changes everything about your outputs.

The AI Agent Promised to Do Your Work. Here's Why It Didn't.

The four conditions that have to be true before you trust an agent with anything that counts.

Every week, one article. No noise.

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