I would put less emphasis on the former player aspect. Time to start training and grooming people. Playing the game does not make anyone a better GM. Scotty Bowman only played minor league. NHL and even AHL former players is a pretty small and relatively uneducated and nonintellectual pool of candidates, not that hockey players are dumb but they don't generally (Dryden and lots of other players did, but still a minority) focus on business/stats/probabilities/sports medecine/psychology. Ex-players know what worked for them, and they know a lot of old traditions, they don't often know what will work for others or for teams. The habs should be hiring and grooming people. Want scouts? Get a bunch of people, have them give a list each year. Wait a few years, go over the lists, see how good they were, see how many were predictable vs guessing. Pro scouting, ask several people for views, see how accurate they are over time. Promote the ones who do best.
I want the habs to develop and hire someone I've never heard of.