I think that lack of trust is the single biggest factor holding back this technology. I imagine that a truly top-notch virtual assistant would always be listen

I think that lack of trust is the single biggest factor holding back this technology. I imagine that a truly top-notch virtual assistant would always be listening and aware of your behavior and context. However, the level of trust required for such monitoring is usually reserved only for one or two people in our lives, and even then, it's quite incomplete awareness on their part. I don't know how a for-profit company can reconcile this disconnect, though I imagine that someone will eventually try.