This depends on his role on the team. He might not be needed to create off the dribble.
Gordon Hayward is a good case study about how his offense creation off the dribble has evolved with his role evolving from a role player to a first option? He went from 68% assisted 2pt attempts in his rookie year, to 66% in second year, to 59%, to 40% last year and is now at 29%. That's very impressive.
Middleton's progression so far is:
63%(very few minutes, so might not be representative) in rookie year, 68% last year, 60% this year? Pretty similar to Gordon, when he's not asked to create. If you ask him to be creator for a year and he has the attributes(handle, some speed and a good feel for the game), he'd probably adjust well to that role too. But again, he might not be needed to create off the dribble...