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First I'd like to say that I think this is a great topic.
My approach, the one that works for me and maybe not for everyone one is:
1. Solicit the input of the target user group - have them become part of the design process. Forget what you think files/directories should be named (unless of course it would cause issues) - let them decide on the conventions, let them decide on interface - help them streamline the process to their liking.
2. Since management wants the tools they must step forward and enforce the use - BUT - the user still will not use it unless they are contributors to the tool.
3. It also seems to help me when I "lead" the user to the solution - this makes them feel like they came up with the idea - therefore making it more palitable to use - rather than having a tool "crammed" down their throats by management and their peers.
Is this foolproof - no. But it will put the odds in your favor - or at least it has for me.
In reply to Re: OT: Getting people to use tools