Technology to help? Can't imagine how that would work... as in a machine to help you socially?
Anyway, my biggest things are
-telling when the topic of conversation has changed, as in whether the thing the other person just said which wasn't completely related to the previous topic was a sidenote my response should return to the previous topic, or if the conversation has progressed and this is the new topic now.
-Co ordinating the topic of conversation with the person, so sometimes I will ask someone I don't know too well or I have a formal relationship with a question which in retrospect should be asked to close friends because it is of a personal nature or has personal information about me or them enclosed in it.
-Shaking hands is a big issue for me. I do not see why people feel the need to physically touch someone they've just met. I mean, what is it, to see if it's an android or something? If they're ice cold, run like hell because it's a zombie? There is no reason for it.
-I need to clarify information several times to process it, so if I arrange to meet someone I spend 10 minutes repeating the time, location, expected duration etc over and over and they often get annoyed.
-Judging how well I've communicated things to others, for example if I think I've made it clear that someone's music is distracting me and I would like them to turn it down, and eventually shout at them, I may find out later that no one else knew that I thought that and from their perspective I suddenly went crazy and started shouting about music.