What are good/bad ways of providing help for an application..?

Answer 1

In my experience nobody but programmers reads the help. So when you have a technical and non-technical target audience you end up providing 2 ways of doing everything:

A Wizard with a few options. A property editor with lots of options.

In either case, pictures are usually better than words for documentation. So a screenshot or 3 with big green arrows and circles calling out what does what will go a lot further than an indexing, exhaustive help file.

Answer 2

In my experience it would be very helpful to have a tooltip on each option that provides a little more definition/clarity for each option. Additionally, you can improve usability by having the default screen contain a few common, simple options and providing an advanced section that provides more control.

Answer 3

I'm currently working on a similar side-project. We have an existing product that's used by people as part of their day job. There is an inherent learning curve on the product, so users receive some degree of training and have people they can turn to for assistance. Even so, we know it needs more help and user documentation in general.

We are starting this help enhancement project by running a quick survey on the end users, (offering a prize draw as an incentive). We will also speak to the support staff who have to deal with help requests. This will uncover some of the pain points, and will give us a clear idea of how to focus our time & resources.

Guidelines on when to use inline tips vs tool tips etc can be found in various style guides, e.g. here:

http://developers.sun.com/docs/web-app-guidelines/uispec4_0/11-help.htm

Bear in mind that it's probably a bad idea to just copy & paste the text from your existing manuals into contextual help tips. You're going to need help writing completely new content. See if you can get some time from a technical writer / copywriter.