What technology options are available?

This may seem like a simple question, but not all organizations, or schools, or districts will have the same technology available to them, including the ability to host Web 2.0 Tools.

Which tasks will a technology need to perform?
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Which technology is better at that task? 

This is important, as technology is better integrated when it is implemented to perform a specific task, and not a vague or unclear task. This applies to Web 2.0 tools, in that one needs to consider specifically what the tool is being used for. For example, a wiki could potentially be used for a discussion, but "discussion" is not a clear enough task, and in fact a wiki would be a bad tool for a moderated, tiered discussion. A discussion board is a much better tool for this.

What will the technology add to the Learning.

As amazing as technology is, and as effective it can be in learning, technology is not always the answer. We can not just plug in a Web 2.0 tool and expect to have learning happen. I once read a quote " It's not the learning tool, It's the learning that comes from the tool".