It's not my boss that's the problem - it's the environment as a whole. "We might get audited, so we need to have documentation available", but the documentation is not kept up to date and is quickly outdated. Agile development is a dirty word around here.

>Welcome to the world of "waterfall methodolgy". Give your boss a good book on Agile development.
>
>>How much is TOO much?
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>>I got requested to make some changes on one of our systems - about 40-50 hours worth of work. I was handed a document with screen mockups and all that - I was pretty happy I didn't have to come up with that myself. First, I have to spend 3 days creating an actual proposal to make the changes. Then I have to spend several days going over the documentation given to me. To top it off, I was just told I need to create another document with all the changes I am going to make to the application. When I asked how that different from the document that was originally given to me, I was told to use the screenshots from that document, but add more details and pretty much specify where I am making the coding changes, and what I was changing it to. So after about 40-50 hours which was the original estimate, I am still drowning in documentation and haven't even got to touch the code yet. The changes are something that could have been covered by 30 minutes of conversation.
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>>Is this normal? At what point does a project manager need to back off and trust the developer?
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>>On a related note, would it be a good idea to shred every single piece of this documentation, throw it in my boss's cubicle, and walk out?