I don't normally pick pocket, but I have played the old thief games and pick pocketing was a bit the same. You had to actually follow and aim at their tiny little belt pouch. But that wasn't an RPG; you succeeded by just being good at playing the game that way.

With how Bethesda's game usually work, I can see this fucking sucking balls trying to follow the NPC while the menu of their inventory is up, unless it's still gonna pause while you decide what to take.