I think you nailed a big topic in the second post. like any quality organization, be it a school, business, government etc., senior leadership succeeds when they are surrounded by quality supporting staff.
I'm warming up to Jr, both in his decision making and the way he carries himself. Being able to connect with young talent is important, and seeing how he's interacting with them publicly is positive to see.
Other than that, today's NHL requires top level people across the board, and the Sharks are still employing some fossils like Sommer. DW should be looking to stock his executive cupboard with fresh talent. That said, I do wonder just how many qualified people there are for these positions. There aren't 32 Tyler Dellows after all.
Ultimately, things start and stop with DW, but that doesn't mean he should bear the responsibility of being the "best" at every faction of hockey ops. Better scouts, better analytics people, etc will help get this team over the top with a GM of DW's caliber