Personally I don't think Williams was ever good enough to really push him. Telles is the first time in a while he's had someone who at least had the hype to be better than him, (plus maybe Blind). Young, Williams and Darmian would get games despite being clearly worse, but that's more on them than him.
Shaw seems to have become quite tough mentally now I think which is an improvement. We know Mourinho almost broke him and IIRC Pocchetino used to have a lot of 1 on 1 meetings to keep him motivated/positive at Southampton. Maybe that's credit to Ole or perhaps it's a simple age/growing up t