Humans don't. "Utility" is part of the map, not part of the territory. We make choices, but utility theory is only a modeling language used to describe choice-making processes.
One are of research you may want to investigate is "Revealed Preference", a concept developed primarily by Paul Samuelson.
"Revealed Preference" has issues, because of things like circular preferences - although it's a mistake to conclude that circular preferences are proof that humans are irrational. Rather, it demonstrates that utility theory in general is just a model, and an incomplete one.
The fundamental issue is that utility, as a model, attempts to compress a topography of many dimensions - human preferences - into a topography of exactly one - a utility value for each potential choice. Impossible Objects - "contradictions", such as circular preferences - are to be expected in the abbreviated topography.
Why is self-reference expected when reducing the dimensions? Is it because these dimensions might influence each other in a circular way?
It seems like a good portion of the whole "maximizing utility" strategy which might be used by a sovereign relies on actually being able to consolidate human preferences into utilities. I think there are a few stages here, each of which may present obstacles. I'm not sure what the current state of the art is with regard to overcoming these, and am curious regarding such.
First, here are a few assumptions that I'm using just to make the problem a bit more navigable (dealing with one or two hard problems instead of a bunch at once) - will need to go back and do away with each of these (and each combination thereof) and see what additional problems result.
So Alice can conclude anything and everything, pretty much (and so can our sovereign.) The sovereign is faced with the problem of figuring out what action to take to maximize across Alice's preferences. However, Alice is basically a sack of meat that has certain emotions in response to certain experiences or certain conclusions about the world, and it doesn't seem obvious how to get the preference ordering of the different worldlines out of these emotions. Some difficulties:
So, to rehash my actual request: what's the state of the art with regards to these difficulties, and how confident are we that we've reached a satisfactory answer?