There is no particular path manager have to take.
Under you're "rules" Ferguson should not have gone from Aberdeen to Man Utd, Wenger should have said no when, as manager of Grampus 8 in Japan, Arsenal came calling. Conte's jump from Siena to Juve should definitely have been done via Spurs as should have Zidane's move when he went from Castilla to Real. What about Mou when he went from Porto to Chelsea, was Porto bigger than a mid table prem club for a stepping stone?
In fact the only person who got it right was Poch and it really paid off as he was brilliant at PSG.