Fire Shanahan, promote Treliving to PofHO. Treliving was nepotism anyways, so I think we are stuck with him. Shanahan was recommended to MLSE by Bettman. I don't have to wonder why he made the team just good enough to make the playoffs but unable to truly compete in them..
Promote Pridham to the GM position. Might as well keep him than lose him to Dubas.
During exit interviews, be sure to tell all players, including the core players, that they will be shopped during the off season, and might be asked to waive their NMCs.
Ask Tavares to consider retirement and offer him a coaching position. If he still wants to play, ask him to waive his NMC.
Tell Money Mitch Marner he WILL NOT be re-signed, so he should provide a list of possible trade destinations.
Tell Rielly he's up to be traded too. He has been a good soldier for our Leafs, but not good enough to go far in the playoffs. Maybe Vancouver might want him.
Trade Woll in a package required to get a starting reliable and more durable goal tender.
Sign Domi to a reasonable contract extension. If he wants crazy money, bye-bye.
Trade anyone that returns great value. The five year window for this rebuild to show any progression towards a championship is long over and has failed misearably. One playoff round win in 8 years does not show much progression IMHO. Matthews, Nylander, Marner, and Rielly are no longer kids. Tavares is older and slowing down now too.
Our Leafs need a new look. It might require more than just a re-tool.