Brian X. ChenAug 6, 2026 – 4.00pmAs a regular user of chatbots such as ChatGPT and Gemini, I thought I had a clear sense of what the artificially intelligent assistants knew about me (like how I’m a father seeking baby gear recommendations and instructions for patching drywall). Beyond that, I’ve never divulged anything deeply personal as I would to a therapist.But when I experimented with some prompts asking what the chatbots had guessed about me – insights they had gathered from connecting the dots across many conversations – I was perturbed.Subscribe to gift this articleGift 5 articles to anyone you choose each month when you subscribe.Subscribe nowAlready a subscriber? Fetching latest articles
What does your chatbot really know about you? Here’s how to find out
You’ll be surprised at the inferences AI agents have drawn about your behaviour from your conversations with them. Try these four prompts to see for yourself.
TL;DRAI
Chatbots infer user profiles by connecting conversation patterns, revealing behavioral insights beyond explicit disclosures. This creates compliance and governance concerns (data retention, consent) critical to enterprise AI adoption strategy.
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