How did Rhianna look him in the eyes and say "yes babe, good album, release it, this is what the people wanted after 7 years, it is pleasing to listen to and enjoyable"?
the real question is how much of the art is their own and how much is outside expectations and their reactions to it.
And it's not always giving in to those voices, sometimes it's going in the opposite direction specifically to subvert those voices and expectations even if that ends up going against your initial instincts as an artist.
With someone like A$AP Rocky, there is a lot of money on the line wrt the record execs but even small indie artists playing to only a hundred people a night have to contend with audience expectation and how that can exert an influence on their creativity.
Im sure it was more like, “hey babe, can I get a few millions to go in the studio and experiment/make some art?” And then she was like, “yeah go for it! Make some weird shit.”
If I was in his position I’d probably be doing the same. Why bother with another top hit that pleases the masses.