Is there a possibility of creating a mentor program where an experienced user helps one or two specific users to get used to the site and its operations? When I had signed up, the complex reputation system and tight quality control(Read:Quick, brutal downvotes) (Edit: of any SE site) were quite daunting, so I'd like to see new users being helped until they are used to the operation of Ask Ubuntu.
I have seen just this week on other SE sites: someone with reputation of 1 ( therefore taking their first steps into a new community ) asking their first question and getting hit with three down votes in quick succession with no comments or answers.
I believe that this happens less often on AskUbuntu and, as many other do, comment when people on low rep get down votes to explain why.
It is a core strength of Ubuntu that the community help each other. For some newcomers it can be difficult finding out how to use the site and how to ask the right questions and how to sort of fit in to how things work here. I don't think it can be assumed that using Ubuntu implies a knowledge of IRC.
I am not sure how a mentoring system might be implemented but I agree with ObsessiveFOSS that it is a good idea to have a way to support people who need it whilst they learn the ropes. I'd be happy to volunteer for something like that.
As a final solution, feel free to add/edit to this community wiki answer.
ObsessiveFOSS states: Maybe permanent, private "chat-rooms" that you can use even with 1 rep can be used to help mentor, along with something like collaborative "session-sharing", where the mentor works with the new user at the same time, whiteboard-style.
I don't think organising training events or specific 1-to-1 mentors is really that required.
Maybe just video/audio of someone for practical intents and purposes reading the Faq(not literally, but you get the point). People tend to disregard anything called faq, but don't mind pushing play.
Good point in the already having videos in the comments, the list of videos is here.
I suppose the underlying point in my response was the way the user has to get there. I don't know of a better way than clicking FAQ, but I think novice users of anything avoid FAQs like the plague.