There's no concept in Bethesda gameplay that says leadership requires proof of managing an organization. If you're going to be the leader of an organization like the College of Winterhold, the game should've offered quests such as the Master level spell quests as requirements, so that it seemed like you definitely worked hard and deserved the position. The game also should've given you an explicit choice if you wanted the position, instead of "you could be a member without progressing" bullshit. Bethesda had several games already with a faction system for a very long time, and yet their vision and implementation of it is still very underdeveloped.
Well, they went from "Do a series of fetch quests" in Oblivion to "Do these four quests and now you're the leader". The Companions arc railroaded you into becoming a werewolf, and it forced you to complete the quest line in order to do the "random quests" that the Companions are supposed to be known for. There is no other way (barring a mod) for you to join the Companions, not become a werewolf, and earn money doing the "radiant quests".
At least they improved the Dark Brotherhood joining requirements between the two games. As much as I enjoyed the assassinations in Oblivion, joining them was a bit immersion breaking. It's made worse that Lucien Lachance was voiced by Wes Johnson who also voiced all of the imperial guards so his roles are pretty much serving as the games crime psychic. I was underwhelmed by the thieve's guild quests in both games. Oblivion's was annoying with the whole Grey Fox dilemma, and while Skyrim's did improve on the whole being a thief angle it still wasn't that interesting.
They should just take away the "become the leader of a faction" aspect of the quest lines - it really cheapens the organization to just take any leader that comes up and then leaves, never to return or to spend rotations on the countless senior ranking guilds the player is the leader of.
It's also a bit disconcerting that you appear to be the only member that can rise in the ranks. J'zargo, Breylenna, and that Nord fellow are always apprentices even though they're supposedly becoming stronger, and the same is true for the rest of the guilds. The Dark Brotherhood is the only understandable quest line in Skyrim where it makes sense that you are the leader. Since the Listener informs the rest of the Brotherhood about the contracts, it stands to reason that the Listener would also be the de facto leader of it. Also, since almost everyone from the original sanctuary dies there are clearly openings among the higher ranks.