It's possible I'm looking at this in a naive way, but is the whole issue with Harry and Milan the title of "Director of Football"?
Obviously in this country, those three magic words automatically conjures up an image of some bitter and twisted failed manager, one who sits on the right hand of the chairman and starts randomly signing his own players, demands changes to the coaching staff and gets paid a lot for seemingly unsettling everyone. By Milan saying that he wants a "Director of Football", and with that commonly head view, suddenly everything seems a bit shaky.
But my understanding is that this guy is being brought in just to offer footballing opinions on the board - so that Harry has more time to concentrate on first team affairs - and also to help out with a future youth academy - once again, so Harry has more time to concentrate on first team affairs - and in doing so, planning for a future beyond Harry and Jim. Perhaps he'll have some part in contract negotiations too, in order to allow Peter Storrie to concentrate more on developing the commercial side of the club, no doubt including the new stadium. I seriously doubt it's anything more sinister than that, after all, Milan's no idiot and he knows he'll never get a better manager.
I just wonder if the whole thing is a case of broken communication of what Milan really has in mind, and Harry being worried and defensive after what happened in May. Obviously the gutter press have tried to make more of it, and Harry and Milan are both strong minded - so once one gets stubborn, the other seems to try his hardest to get their point of view the "accepted" one - but is it really just a case of not understanding the other's point of view?