What experienced GM wants to take a job where the boss man is basically babysitting him though?
Jackson's going to hire someone that has shared philosophies and is a team player within their management structure. He demonstrated that through the Draft and Free Agency which he credited the function management leaders for guiding them through. Probably the best evidence is following through on Pracey's request to move into the 1st round to snag O'Reilly. Huge trust in his staffer to follow through.
JJ has steadily build his strategic vision, identified management functions to change or upgrade (Head Coach, Director Amateur Scouting, senior Analytics support function, Development), and due to circumstances their reality is the GM position is the remaining big piece to fill.
I don't perceive anything in his career history suggests micromanagement tendencies other than an awkward transitional collaboration with Holland and his expiring contract.
This is a big money franchise that won't cut on financial corners, was 2 goals from a Stanley Cup, and McDavid and his running mate in prime years. Incredible opportunity for the right fit on experience, innovative mindset, and collaborative, team player.