- I find the system confusing.
- I'm intimidated by the many rules and guidelines, particularly as getting things "wrong" seems to carry penalties.
- Figuring out how the whole system works, particularly which questions are "OK" and which aren't, is way more work than I'm willing to spend for the occasional question that you can ask elsewhere just as easily.
Put quite simply, some people grok the SO method and system far more easily than others. Some people go bug-eyed at needing to absorb such a complex system; other people "get it" right away and go, "YES! This is exactly what I've been looking for!".
If somebody seems interested but confused, you can (A) give them a basic primer to the site, including the concept of rep and how the strict Q&A format makes helpful answers immediately visible; and (B) assure them that they can learn pretty much everything as they go along. It's also worth making clear that a few mistakes early on are entirely inconsequential (even if it might not feel that way...). If somebody is still interested but worried, you can offer to help by looking over their posts before they go live.
If somebody seems opposed to the whole affair, don't bother evangelizing - it's more likely to annoy than anything else. If a person is already doing fine using other resources, or simply doesn't like the system, there's no reason to urge him to "get used to it." SO is one resource among many, and hardly to everybody's taste.
- It is hard for a newcomer to build up reputation, even to the point of basic usability.
- People aren't upvoting my posts to the degree that I think they deserve.
Many newcomers, excited at having a "score" want to see it climb right away. Currently, with SO as busy (and full of experts!) as it is, that doesn't really happen from casual use. Help manage their expectations; emphasize that reputation score is an extra bonus and not the main point of the site; if they really want to put effort into gaining some initial reputation (e.g. at least enough for basic functionality), you can help them out by pointing out where they're more likely to do so well (ask great questions in popular subjects; follow topics you have particular expertise in and try to get answers in right away; possibly even start out on a sister-site where rep might be easier, and gain the association bonus).
- I'm not getting helpful answers to my questions.
There are many reasons a question might not be getting helpful answers. Some are avoidable. Go over his questions; see if they're clear and answerable; check if they're tagged correctly so they're seen by the "right" people. If it's a good-but-obscure question, and you've got the rep for it, you might even play Alturist for a friend, putting a bounty on his question.
Tone and Atmosphere
- It feels like everybody's so pedantic.
- Why are people bugging me to accept answers?
- It feels unfriendly to newcomers.
- Why are my questions being closed? I hate this site!
Some of this is mentality - some people get along better with constant "constructive criticism", others less so. Some is the natural cruft you get on any site big enough.
If somebody doesn't like the tone of the site, that's perfectly reasonable. You can put the question to him whether other sites are better - and maybe utility outweighs inconvenience! - but the choice is ultimately his.
You can, again, peek over his shoulder to make sure he's using the site in a way which will cause minimal friction... and assure him that you get used to the local mores pretty quickly, and get a feel for what'll work well and what less so (and also who's being a jerk, and who's being helpful). With time, he'll also be able to raise flags and respond better to any less-appropriate hassling that may remain.