AI Masterclass

Why AI feels frustrating, and what to build around it.

Rory Otterburn and Tancredi De Pretto on the missing piece most teams never build: context. Recorded live on 2026-09-17.

53 minutes · Rory Otterburn, Rabbit · Tancredi De Pretto, Head of AI Coaching and Training

What is in it

00:17

AI lacks context about your job

Why it is phenomenal one minute and frustrating the next, and why you have to feed it curated context.

05:18

Most people use AI like a chatbot

Conversation is part of the job. The gap is getting from conversation to execution.

10:13

Probabilistic, not deterministic

A model can reach 99%, never 100%. That sets how much you can safely delegate.

12:31

The harness

The system you build and operate around the model to narrow the chance of bad output.

38:39

You are the art curator

You decide what is valuable. The AI does not.

Who is speaking

Rory OtterburnRabbit founder
Tancredi De PrettoHead of AI Coaching and Training
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