Thinking
October 2026

A friend who runs hotel bookings let ChatGPT plan her own trip.

A friend who runs hotel bookings for a living let ChatGPT run her own trip. Itinerary, car rental, hotel shortlist, all of it. She checked two or three of its suggestions, then booked the stay herself, the usual way.

If someone who runs hotels does this for her own travel, her guests are already doing it too.

What stood out to me was what she actually gave the AI to work with. Not price range, not star rating. A feeling, private, quiet, specific to her own taste. ChatGPT matched hotels against that, not against generic categories like luxury or five star.

That is exactly where most hotels lose the match. A website full of words like exceptional or unforgettable gives a machine nothing concrete to work with. A website that says precisely who stays here and why gives it everything.

Whatever decides who makes that shortlist has already happened, long before anyone compares prices. For any hotel working on its identity, that clarity is the first thing worth getting right.

Originally posted on LinkedIn, October 2026.

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