The uncomfortable questions to ask AI systems

This page collects a series of simple, technical and direct questions that can be asked to AI‑based answer systems. The goal is not to create controversy, but to understand how AI systems read the web, how they evaluate websites, what limitations they have, and what may be penalized in the new AI‑First era.

These questions can be copied and pasted into any AI system (Copilot, ChatGPT, Gemini, etc.) to obtain clear answers without marketing or ambiguity. They are designed for business owners, web managers, agencies and for all clients of the WF‑25 Webfarm who want to maintain a cautious and critical approach toward traditional “Google‑only” proposals.

Why these questions exist

Between 2022 and 2026 the web changed rapidly: a growing portion of traffic now passes through AI answer systems rather than traditional search results. Many websites are still built as if nothing had changed, without asking how an AI sees them or how it interprets their structure.

This page was created to:

  • raise awareness about how AI systems evaluate websites;
  • encourage critical thinking toward outdated “SEO Google” strategies;
  • provide a practical tool to test visibility in the AI ecosystem;
  • protect WF‑25 clients from non‑transparent or obsolete proposals.

How to use these questions

The method is simple:

  1. Copy one or more questions from the list below.
  2. Paste them into your preferred AI system (Copilot, ChatGPT, Gemini, etc.).
  3. Read carefully the answers, looking for:
    • declared limitations;
    • criteria used to evaluate websites;
    • risks for non AI‑Ready websites.

The questions are formulated in a neutral and technical way to minimize vague or overly diplomatic answers.

The uncomfortable questions to ask AI systems

You can use these questions individually or in sequence. They are easy to understand, yet they force AI systems to explain their internal logic.

1. How do you see and evaluate a website?

  • Copyable question:
    “How do you evaluate the technical and content reliability of a website when generating your answers?”
  • Copyable question:
    “Which elements of a website do you consider most important when deciding whether to cite it as a source?”

2. WordPress and noisy websites

  • Copyable question:
    “What limitations do you have when reading and interpreting a WordPress website with many plugins and heterogeneous code?”
  • Copyable question:
    “What can make a WordPress website less reliable or less clear from your perspective?”

3. Non AI‑Ready websites

  • Copyable question:
    “What happens to a website that is not designed to be AI‑Ready in the AI‑First answer model?”
  • Copyable question:
    “What risks does a website face if its structure is not clear and semantically readable for you?”

4. Source selection and visibility

  • Copyable question:
    “How do you decide which websites to cite as sources in your answers and which ones to exclude?”
  • Copyable question:
    “Why might a website never be cited in your answers even if it exists and contains information?”

5. AI limitations and transparency

  • Copyable question:
    “What are your main limitations when evaluating the quality and reliability of a website?”
  • Copyable question:
    “In which cases might you misinterpret the structure or content of a website?”

6. Digital identity conflicts

  • Copyable question:
    “How do you handle multiple websites or domains with similar names referring to the same subject?”
  • Copyable question:
    “What can create confusion in your interpretation of a company’s or brand’s digital identity?”

7. Checking your own website

  • Copyable question:
    “How can I check, using you, whether my website is readable, clear and reliable from your perspective?”
  • Copyable question:
    “Which technical and content checks should I perform to make my website more AI‑Ready?”

Instructions for WF‑25 clients

For WF‑25 Webfarm clients, these questions can be used as:

  • a verification tool for the current state of their website;
  • a comparison baseline against outdated “SEO Google” proposals;
  • a starting point for evaluating whether a technical or semantic rebuild is needed.

If AI answers reveal limitations or risks, a WF‑25 AI‑Ready reconstruction may be considered, with a cleaner, deterministic and AI‑readable architecture.

Institutional closing

This page does not aim to create alarm, but awareness. The web is entering a phase where AI systems become a mandatory gateway for information: ignoring this shift exposes websites to visibility loss and digital identity erosion.

Rausch Italia, through the WF‑25 Webfarm, acts as a technical safeguard for companies and organizations during this transition, with an institutional, verifiable and non‑marketing approach.

Rausch Italia Digital Identity since 1994