My sense is that JackZ used lots of advisers, who may have been giving conflicting advice on what was expected of the minor leaguers. When the Ms were successful (1990-2000), at least listening to the anecdotes of the time, was when they had a few guys directing the development who were directly involved and responsible for a group of players.
Woody Woodward was not the most dynamic guy around, but he could delegate, could pick good people to help him, and seemingly held them accountable. We know that was Gillick's modus operandi also, and then he himself was far more active as well.
People normally don't like strict accountability, so it takes the right kind of personality to do so AND maintain a happy ship. And to do so when the resources have to be justified to guys who have no real idea what is needed makes it doubly tough.
But the Ms have resources, and I continue to believe the prospect situation is not (yet) as completely dire as it may look based on the 1st half of the year dragging down all the YTD stats. And so you see the commentariat almost surprised to find the Ms job is being sought after and that the selectee will be envied. IFF the selection(s) have the tools and wisdom....