Documented?

So, I'm taking over the technical management of a web service. One of the first things I did was talk to everyone, mostly to check the temperature. The kinds of questions I asked were basic. If you ask a basic question, you get a better answer. And one of those questions was What can we do better? The one unanimous issue was that we needed better documentation.

Great. Only two problems with this.

1. Most of the team doesn't write well.
   
2. In the past, nobody has gone out of their way to really make documentation happen.

Why I point this out: most teams probably think that this is just a scheduling problem. As if you just added some time for Documentation, the problem is solved. I think if you just added more time for documentation, people will just half-ass some crap on the wall and probably spend the rest of the time you slated for documentation surfing the intertubes.

I need a strategy. I need a system that will help bad writers get better incrementally. Which means that everything must be painfully obvious. The first pieces of the puzzle are the stuff that actually exists, which are the most important parts, anyway.

• Code/API Documentation — What does your code do? Especially, what side effects are there?
• Adminsitration Guide — How do we run the system?
• Users Guide — How do users run the system?

The other part is planning. Essentially, you need to identify groups of features, and then answer two big questions for each feature set. One, what's the business value here? Or, how do we get paid? Two, how is this thing going to work?

I'm not sure I've not forgotten about something completely hugemongous.