By the time SAF and Gill both retired (on the same day), they had complete and telepathic control of the club. They were completely in sync with each other, knew each others duties and boundaries, and there was complete trust and zero politics between them. Together, they were one, and completely manifested 'what' Manchester United was.
I don't think fans realise the enormity of the organisational vacuum they left behind, and subsequent leaders have had to completely re create within that context. That situation was compounded further by Moyes decision to also rid of SAFs backroom staff, and by Woodward's desire to get more involved in the football side of the organisation. Over a period of sacked and new managers, so the organisation and culture has pivoted and evolved into where we are now.
Unlike some, I don't criticise Woodward's intent: he has invested heavily and tried to hire the best on the footballing side, whilst continuing to excel on the commercial side of the club. Unfortunately for him, he inherited the Moyes appointment, was not savvy soon enough to stop Moyes sacking SAFs backroom and has allowed his managers to make some very poor footballing decisions (eg extend Rooney contract, allow LVG to decimate the squad, not back Mourinho in his final year), and that seems to be the consistent area of weakness for him. Of course there is also no guarantee that had Woodward appointed a DoF of Football, like Txiki Begiristain, that this mess would have been avoided, but in not doing so, it's a stick he can now be beaten with.
However, Woodward now also has 10 years experience at Manchester United, 6 as CEO, and in that time he has been exposed to footballs top secrets and methods, he is no longer 'just an accountant' who 'knows fcuk all about football'. By now he should be a seasoned expert, able to frame and articulate a footballing vision, that his manager's and support staff should execute. I really hope he contributed significantly to this new longer term strategy and is truly invested in it. Because he now has the experience to execute it.
Personally, Im willing to wait til Guardiola leave man City, but that's the moment we have to pounce and win the league the following season. Until the we should all be satisfied with gradual progress. Im willing to give Woodward that last try: I think his motives are good, just need him now to perfectly execute.