Darren Fletcher's role at United is very different to the role Maldini is occupying at AC Milan. Maldini is the head of the football departments at Milan, whilst Fletcher first joined as a youth coach and was then given more responsibility by the full-time managers, where he is reported to be helping direct the first team coaching staff on who should be making the step up to first team training aided by the likes of Nick Cox. So he was promoted from coaching the youth full time to helping select which youth players were ready to step upto first team training.
What some of you need to ask yourself is, that do you even want to attempt to learn what the likes of Fletcher do or carry on being led astray by a title given to him. The actual technical director helping oversee the football side of the club is Andy O'Boyle. And from what's been reported, he hasn't only been assisting with transfer negotiations at first team level but also oversees the academy/recruitment since he arrived late last year.
And Italian football clubs don't produce football managers but rather they produce football players who are influenced by other football people which shapes their coaching career. Arrigo Sacchi was the revolutionary coach at Milan in the late 80s and he was heavily influenced by the Dutch team of the 70s. Ancelotti himself was influenced by the Swedish coach Nils Liedholm in his own words when the Swede was managing Roma.
Arrigo Sacchi “The last 50 years in the sport have been a constant evolution from Ajax to Holland, Milan to Guardiola’s Barcelona. Without evolution, the sport is dead. Without risks, you remain in the past, whereas innovation makes you change every year."
“In Italy, we have this short-term view of everything and want to stop time, stick with the past. Pessimism blocks your brain. If you play in defence, how can you grow?”
https://football-italia.net/ancelotti-sacchi-pep-on-mentors/
Sacchi's words still ring true today imo. Italian football hasn't evolved as much as other big leagues and we still see general managers and DoFs attempt to implement a dated method of football., with the exception of a few teams.