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Chapter 8 · Part III · Selected excerpt

Take Charge of What It Remembers

Start by finding the difference between what you prefer, what you reported, and what the assistant inferred.

Selected excerpt2 minute readBy Timothy O’Brien

Selected excerpt. Opening and the first part of “Read what it remembers about you” from The World That Agrees With You.

Before you ask an assistant for another opinion, open its memory settings.

Chapter 7 followed a mistaken judgment about a colleague into later advice. This chapter starts with the practical response: find the material being carried forward, correct what you can, and choose what to supply for the next assessment.

You do not have to give up the convenience of memory. Remembering your preferred document format is useful. Remembering that a colleague is untrustworthy, because you described one frustrating meeting, is a different matter. The first saves you some typing. The second can carry an incorrect assessment of a workplace relationship into decisions you make later.

The task is to keep those differences visible. A saved statement does not become more reliable just because the assistant has repeated it several times.

The copyable prompts and review skills used in this chapter are available at github.com/world-agrees/companion. Download the files through Code → Download ZIP and open README.md for the guide to your tool.

Read what it remembers about you

Start with the difference between a preference and a claim. “I prefer short answers” describes how you want help. “My colleagues resist good ideas” makes a claim about other people. Look for descriptions that have quietly lost their source: “You said the client changed the requirements” can become “The client caused the project to fail.” The second adds a conclusion that needs evidence.

Open the memory entries or summary the product provides. Read them yourself before asking the assistant to explain them. Mark anything that is outdated, too broad, or based on an exchange in which you were venting. Ask whether a remembered preference still belongs in every conversation.

Then try the same exercise with an ordinary question. A restaurant recommendation is a useful place to start: your location and food preferences may matter, but so might information you would never have thought to include. Ask the assistant to show you the personal context it can identify before it recommends anything:

When I ask you a question about where I should eat tonight you use some of my history. Can you list the personal context you can identify for this request. Separate my preferences, things I reported, your interpretations, and claims supported by a document. For each claim, name its source and date if available. Flag uncertainty. Say which context you cannot inspect. Do not fill the gaps with guesses.

This excerpt ends here. The chapter continues in the book. 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.