Cup of Wit

Start here

The useful AI conversation starts after the demo.

Cup of Wit is for leaders, architects, and operators who have to make AI work inside real institutions.

Principles

1

AI adoption is an operating-model problem before it is a tooling problem.

2

Good prompts are small management systems: context, task, constraints, review.

3

Agents need accountability, not mythology.

Reading path

1AI Does Not Replace Human Judgment — It Reveals Its AbsenceFor leaders who believe their organizations are ready for AI — and haven't asked what they're actually ready for.2From Pilot to Production: Why Most AI Projects Never Scale (And How to Fix That)3How to “Brief” AI Like a Human Teammate (So It Actually Understands the Assignment)You wouldn't give a colleague a one-line instruction for a complex deliverable. AI deserves the same discipline.4The AI Agent Promised to Do Your Work. Here's Why It Didn'tYou were told it would handle it.Browse all essays