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Re:I ask 100 information questions to four digital assistants by ghaff on Friday June 30, 2017 @02:06PM (#14672559)
I think a good model to imagine is that you don't have any computers on you and you're talking to an assistant over the phone who has access to Google and other online resources. The types of responses you'd expect from that at least modestly intelligent assistant are probably not all that different from what you'd like to hear from a digital assistant.

If I were to ask a question that had a long list of potential responses, I'd expect them to ask me to clarify or narrow down what I'm looking for or at least explicitly ask me if I really wanted them to read the whole list.

Re:I ask 100 information questions to four digital assistants by bluGill on Friday June 30, 2017 @05:21PM (#14673674)
I'd expect my assistant to know a fair amount about me and the current context. Using those clues a human can pick out what I really care about, at least in most cases. Even when there is a list of responses I'd expect an assistant to give a better summary when asking for clarification.
Re:I ask 100 information questions to four digital assistants by ghaff on Friday June 30, 2017 @06:22PM (#14673917)
Certainly learning my preferences is an important component of a personal assistant. e.g. I almost always go to the airport using a particular service.

That said, for those of us who don't have personal admins, there's a lot of opportunity for digital services that fall between purely self-service travel booking as it exists today and and having an assistant.