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As others have implied, the question here is whether your boss wants dancing pigs or chrome or pizzazz, or would rather have something innovative that actually helps the user. So many bosses are dazzled by dancing pigs. Maybe some users are, too.
The best thing you can do to make the help helpful is to figure out what people have trouble with at any given point in the application/wiki/whatever. Then make assistance with that easily accessible, while also making deeper assistance with the non-immediate problem available too.
I would do these things, assuming they make sense in context:
1) have a HELP icon that presents the thing people most often have trouble with at that point
2) Have tooltips for fields and buttons that give a quick summary of what the thing does. Most of these aren't helpful, but you may as well do them.
3) Have a help menu (or something) that lets users choose among:
"What do I do next?"
"I want to..." that has procedure descriptions and sends them to the right place in the app/blog/whatever to do that.
A FAQ list
Some kind of reference doc for people who really want it. Some will.
Except for the reference doc, I would make the text of all these things as lean and direct as possible. Even in the reference doc I would keep the intro and blahblah to a minimum. And I would have a kickass index.
Maybe all these things are old fashioned. But I've seen them work with complex web apps.
If your boss wants chrome, there are a zillion zippy choices, many of which will look old-fashioned a few nanoseconds from now. I can't help you with that.
- Jessica, wearing her curmudgeon hat which gives her terrible hat head
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