Fresh idea, straight out of the game: I my opinion, a lot of player wants
micromanagement in guild's questlines.
As a general direction, it would be definiately a nice one. You know, like opportunity to own a tavern and lead it, to be a real merchant and so on. But to stick to the topic (guilds), being able to recruit new members to your guild is a common request, to give assignments to them is another, to have an impact to their development would be also great.
My character had a little converstation a few minutes ago with Phinis Gestor (Conjuration Master of College of Winterhold), when our bald friend mentioned his former mentor, Falion. He left a College a few years ago, because - and here comes the interesting part - he had differences with the Arch-Mage, namely Savos Aren. So one day he packed his stuff, and left Winterhold. Since we know, that ...
Spoiler ... Savos died in the College's questline and the player replaced him as a leader ...
... why we can't persuade Falion to return to teaching? Or why we can't reorganize the whole institution? Let's say you need one specialist for every magic school, that's a fair restriction, but who holds that position is up to you. Maybe some hard coded skill-check should be implemented to ensure you don't hire untalented persons.
You can say that the College already had the best magic masters - but its literally the half of the truth! While they indeed have the most competent ones is Alteration (Tolfdir), Destruction (Faralada) and Illusion (Drevis); in Conjuration (Falion), Enchanting (Hamal) or Restoration (Danica Pure-Spring) the world offer better options! And anyway, what if I want to see Dravynea in Tolfdir's seat just because I like her much more, why can't I do that?
Spoiler May I remind somebody who is in charge in here?
Mentioning Tolfdir serves a special purpose, since ...
Spoiler ... he promoted to Master Wizard after the death of Mirabelle, so we have one position to fill anyway - Alteration teacher or Master Wizard! Would be nice to be able to appoint both manually!
Not mentioning those scholars residing at the second floor of Hall of Countenance, they mostly practicing magic in theory. There can be easily replaced since almost none of them have and actual quest. Why can't I kick them out to promote my fellow mage buddies (Brelyna, J'Zargo, Onmund), who was with me from the start? Or why can't I give a second chance to Orthorn? Why can't I put J'Zargo in a position responsible for the College's Affairs to the citizens of Winterhold?
LOL, the last one was a joke ofc. The point is the usual: another would-be-so-cool feature without a tremendous amount coding, what we probably won't see from the official developers. And the logic I explained mostly applies to the other Guild's questlines too.