Let's take the Thieves Guild for example. You can take numerous jobs from Delvin and Vex that have you going to one of the five major holds of the game and carrying out different missions for the guild. A lot of people don't like these, but I rather enjoy them. Sure, I wish they were a bit more in depth, but its better than nothing.
Now doing these small jobs is all well and good as a new member of the guild but the mechanics should fundamentally change once you actually become the guild master. Here's how it should work.
You should, first of all, have your own chambers. And on your desk there should be requests from people wanting certain thing done, bedlam jobs, heists, shill jobs, etc. It should be in the form of a letter and have the "customers" name and what they're wanting done. You should be able to negotiate with the buyer on a price, and depending on your speech skill, he or she may or may not accept your offer. Once a job is agreed upon you have a couple of choices.
First, you can take the job yourself, in which case you do not have to pay another member of the guild their cut. In other words you get more back for it once the job is done. Or you can tell one of the many thieves in the guild that they need to do the job, in which case they will earn a cut. Now, you won't get as much gold back from this but its easy gold as you literally don't have to do anything but wait and you'll get a percentage, again, whatever is agreed upon.
There's so many other possibilities as well. Take for example, bringing in new members. Potential thieves could come to you, want to be part of the guild, you can test them and decide, etc. There's a great number of possibilities but the main thing for me would be changing the way the guild works once you're the leader.
As it stands now you still have to go to Delvin or Vex for jobs. Which is kind of silly in my opinion. I just role-play that its a job that I've decided to take myself, rather than delegate.


