The book’s vocabulary

Devil’s advocate review

A second model asked to help the work by attacking it honestly.

From The World That Agrees With You2 sections of the book2 related posts

A second assessment of substantial work, ideally from a different model and provider: does the document hold up? It checks facts, tests assumptions, and looks for gaps that would matter to the reader — helping a sound document succeed and showing what a weak one needs.

Asking a model to find fault with everything simply gives it another performance to deliver; asking for encouragement begins by congratulating you. Ask it to help the work by showing what holds up, what needs revision, and why.

Definition from The World That Agrees With You: Understanding and Managing Sycophancy in the Age of AI, by Timothy O’Brien. © 2026 Timothy O’Brien. All rights reserved.

In the book

See also