The Manual
Vol. I · No. 1 · September 2026
The Gentleman's Guide
Part VI · Digital & Tech SafetyNo. 220 · Page 8 of 20

AI tools, using them well

Treat AI-generated answers as a starting draft to verify, not a final authority, especially for anything factual, legal, medical, or financial. The tools are genuinely useful for drafting and brainstorming — just build the habit of double-checking.

AI tools, using them well

What the thing is doing

A chat assistant is built on a language model, which produces text by predicting what plausibly comes next. It was not built to look facts up, although some versions can now search the web as well. That explains its characteristic failure, which is an answer that is fluent, confident and wrong. These tools invent citations, quotations, statistics and court cases that look exactly like real ones, and lawyers have been sanctioned for filing briefs full of them. A model also has a training cutoff, so without a search feature it knows nothing recent.

Where it is strong and weak

It is good at work whose quality you can judge for yourself. That covers first drafts of emails and cover letters, summaries of a document you paste in, rewriting for tone or length, explaining a concept at three levels of difficulty, brainstorming names and outlines, practice interview questions, and small pieces of code. It is weak wherever you would have to take its word, including niche facts, precise figures, local law, medication questions, anything that happened recently, and anything about you that it has no way of knowing.

Asking well

  1. State the context and the audience, because a note to a landlord and a note to a friend are different jobs.
  2. Give it the raw material, and tell it to work only from what you have supplied.
  3. Specify the format and length you want, and paste in an example of the style if you have one.
  4. Tell it to ask you clarifying questions before it begins.
  5. Treat the first answer as a draft, and say what is wrong with it rather than starting over.

Verify like an editor

Check every name, number, date and quotation against a source that you open yourself. Asking the tool whether it is sure proves nothing, because it will agree or apologize with equal ease.

What not to paste in

Assume that a conversation may be stored, reviewed by staff or used for training unless you have found the setting that says otherwise. Keep out Social Security numbers, passwords, medical records, other people's private details and your employer's confidential material. Many workplaces and schools now have written rules on these tools. Read them, because your name is on whatever you hand in.

Tip Ask the tool to argue against your plan or to list the weak points in your draft. It is more useful as a critic than as a cheerleader, and left alone it will tend to agree with you.