I'm thinking there's a lot of ways that works. For one thing, there's the intersection of reader and writer squids, or the thing that I call "target audience," much to the dismay of some of my buddies. This is what happens when a reader and writer connect on some emotional, and the one groks the other in fullness. Usually, I think, somebody's favorite storytellers are in large part determined by that intersection of squids.
Beyond that, there's the next level of love: these are the readers who bring a different 50% to the story, interpret it in ways the writer never would have seen, and still walk away with a coherent story in their heads and a sense (greater or lesser) of having been entertained and satisfied.
And then there are the readers who do not connect with you and cannot be made to. Watch them walk away. Bye bye readers.... :-(
I think that any writer can learn to connect better with all of these groups. On the other hand, no matter how good he gets, I suspect there will always be that last group of readers, who for whatever reason cannot connect with that particular style of communication. The trick is to find a significant quantity of audiences (1) and (2).
All of this, of course, presumes that the writer is writing on a refined enough level to be able to approximate the story he wanted to tell in the first place.