Rebecca Chernoff asked: New users often are not accustomed to the Stack Exchange system, and sometimes struggle to present themselves properly, either in the way they use the site or their attitude. How willing are you to work with "problematic" users, and at what point do you decide that someone isn't worth the effort?
Rahul answered: I always try to go the extra mile for new users because I feel like the UX offered by SE sites currently isn't as good as it should be and I'm very sensitive to that. Often there's also no one else there for them, so as a mod I feel like it's my responsibility to at least make that effort.
Rahul continued: I usually stop making an effort if the user doesn't respond after a week (eg. they never came back - you can check on their profile) or if their language is incomprehensible, which unfortunately can happen with non-native English speakers.
dnbrv answered: First, use the comments to explain what the problems are, and then invite them to chat or Meta to discuss the issues in more detail. Recently, there have been several new users who came in with overly broad questions that got closed. They complained, we tried to explain. In the end, the users left. We also had a couple of new users who were posting low-quality replies. After comments, some of them greatly improved their style & others left.
Jon W answered: That's the main role of the Mod at present, I believe. encouraging new users to become regular users the site and not just people who post-and-run, never to be seen again. New users need to be given more consideration than others so they're not scared off.
Jon W continued: ..That is hard though, if people are flagging and voting to close questions off. If we can keep these questions open, keep them involved and guide them into rewording it (or even letting them accept it may need to be closed, but as friendly as possibly) then so be it.
Ben Brocka answered: I always try to help out these users by asking clarifying comments ("Are you asking X...To what ends do you want to know...") or editing their posts where appropriate and explaining how they can make their posts fit better with the Stack Exchange model.
Ben Brocka continued: I like trying to help "problematic" users when they are learning to use the system, but if someone clearly has no respect for other users, the Stack Exchange Q&A model I would begin to consider them a lost cause to be dealt with punitively rather than a student to be encouraged