When John Armstrong, North America leader for IBM Interactive Experience, was planning a trip to Iceland with his son a few years ago, he wanted nothing more than to speak to one of the numerous websites he used for researching the excursion what he wanted.

“I wanted to say, ‘Look, in the next six months I’m thinking of taking a trip to Iceland with my son. Here is approximately what I want to spend. Here are the types of places I want to stay at,’” Armstrong says. “We’ve been chasing personalization forever in this space. We take a bunch of data and then we try to figure out what the shopper wants. Wouldn’t that be great to just be able to ask? To just talk? And if the system doesn’t quite get it right the first time, to say ‘Well, sort of, but let me tell you a little bit more.’”

In short, Armstrong wanted what IBM Corp. is seeking to deliver with IBM Watson. IBM thinks there is big business in “conversational commerce”—using technology to enable a more natural back-and-forth in facilitating transactions—and it has invested heavily in developing it over the past three years with its Watson supercomputer. For example, a center IBM opened last year in Munich seeks to bring Watson…

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