My biggest worry with Harry has always been Harry...
He HAS done a good job, no denying it, but the very things he's good at are things which (in the last two seasons) he has failed to get done in the Feb-April portion of the season...and that is man-manage and squad rotate properly. These are things he was always very good at, and has been with us, but once again, late winter/early spring has seen it go a bit "tits up"...now, I speculate that it is because Harry has had Harry stuff to deal with, and such Tottenham have not been his 100% focus.
There is little doubt that he is not always tactically ruthless. I think he "knows" what should be done, but sometimes allows sentiment (and the media) to get in the way. Example; we hammer Saudi Sportswashing Machine 5-0, could've been 8 or 9. Press goes bananas, Harry-Messiah-England, blah blah blah; critically, everyone ignores the fact that Newcash were missing their midfield heart and that Pardew had come out and publicly said the defeat was his fault for taking a 4-4-2 to the Lane with a weakened side. Now, any sane person who has watched/played football longer than a year will know that when going to the Emirates as hot favorites, the one thing you want to do is be patient and be clinical. No need to swashbuckle, just put in the sort of strong way performance with 4-5-1 which has been happening all season. Instead Harry, inexplicably, decides that the same formation/side which smashed a weakened 4-4-2 Newcash at home, is the right approach for the deathstar; I call it sentimentality/naivity.
Again last Monday against Norwich, we go 2-1 down, their defense is wide open, we are making chances, yet Harry panics with 20-25 mins left and decides to take off our holding midfielder, leave Modric basically alone, and has VdV, Ade, Defoe and Bale all attacking as forwards. That is PS3 stuff. With patience and SHAPE, we could have come back and won that game, but by throwing the kitchen sink without rhyme or reason, we ended up lumbering the architect of the side by crowding him out with strikers. It was absurd IMHO.
And right now, at the moment when Harry needs to come to the party, he appears unsure and indecisive. Where's the public bravado and strength?
I have to believe there's stuff going on we don't know about, because honestly, some of his decisions since Feb don't make sense given the experience and previous decent decisions in similar match circumstances he's made.
if he is to manage us for the next few years, these are problems which need to be comprehensively answered IMHO...