[vidarh]

A lot of it is simply about learning when you know enough and when you need more information through the interactions themselves. If you have to "set things up" it seems tedious. If it's just conversing with you about the information it needs, and gradually learning your preferences, that's different.

I used to fly in to the Bay Area very often on business. At first the office manager arranging things would ask me details about which airline and which flights I'd prefer after listing the options, and which hotels, describing address and location and how near they were the office. Possibly e-mailing me a bunch of links for me to look at. But after just a few trips it was down to "is flying out on the 2.30 on Wednesday and returning on the 3.15 the following Thursday, ok? [she know when I preferred to fly, and she'd implicitly have ensured they were the right code to maximize my chance of an upgrade] Your usual hotel is full, is the Sheraton ok?" [no addresses necessary - we'd boiled it down to 2-3 preferred hotels within walking distance of the office].