[PascalsMugger]

Just curious, but why do you refer to it as "he", especially in this context where you are touting it as an actual non-human? Not to single you out, I see people referring to all these other things as (usually female) "her" and it just unsettles me to think that people are anthropomorphizing these things so much.

On a related tangent, often these same people will refer to animals as "it", too, which is even more curious. A living being with an actual gender doesn't rate a gendered pronoun, yet a piece of software does.

[mmatty]

True. We started out trying to limit the conversation to just scheduling-related topics. But very early on we realized that since this is all happening in a conversation, people expect him to be able to carry some smalltalk - because when he doesn't, he's perceived as stupid - he can't even say "hello" properly, how can he possibly do scheduling? (if this is interesting, I wrote about it a few month ago in much more detail: https://medium.com/building-the-robot-assistant/cheating-on-... )