Complicating the situation is that I don't trust any of the companies making virtual assistants with this level of personal data; so the first thing I do on a new device is block the assistant's access to my location or any other behavior learning functionalities.
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.
I believe tech companies are aware of the creepiness factor associated with surprising customers with too much context about them. I think they cripple some of the more context aware features that they could be doing because it draws a lot of attention on just how much data they have about you.
That could maybe be gradually introduced like that story about the frog which doesn't feel the water getting warm. What put people off is having it knowing everything up ahead through inference on data you were not even aware you had shared.
Instead, you could go easy, by first suggestint the user to set up your assistant by linking it to amazon, deliveroo/uber eats/etc, facebook, and verbally sharing information as it asks. Then, over time, it could spread its inference further and further and you won't be sure or not if you already shared that information or not, but you will just assume you did, as you share everything anyway. For people who are not so open, it could stick to inferring less and being less useful.
I would want a company where I pay them for their assistant, knowing that everything it holds is not shared with anyone and completely under my control.
The issue is of course, like paying for youtube, is consumers will wonder why they would want to pay for an assistant.
This is a complicated social construct even with people. If a public relations person (or whoever in a professional context) reaches out to me, I hope they've done some basic research on what my interests are. I saw you were at $CONFERENCE last month? Sure, probably. Start asking me about my vacation last month that they found photos from on Flickr? Probably getting over a line if I don't know them.
