Edit: I mean, no high–tech, but tools with a higher level of complexity where the UI isn't a dumbed down version, and where the software exposes some functionality to a better skilled user. I'm thinking the "millennial" professional, should be more comfortable with software and pushing the limit a little bit.
The obvious suggestion would be to have internal groups (excluding legal) collaborate on some common plaintext markdown format where DVCS tools would provide an advantage, then publish to docx and hand over to legal for review. Unfortunately what always happens is that major changes to the contract are needed after legal has done their work, and it's easier (and acceptable) for all groups to work on the final paper together. That's where it breaks down.
I really feel that in 2016 having some poor bastard do clerical coordination of this stuff is just wrong. It's a mechanical task that's highly both error prone and a major source of operational risk, and it should be doable by the computer.
I actually kind of want to build this. Word (and the rest of office, I have the same problems with spreadsheets and powerpoints) plus plugins as the IDE, solid version control in the backend.
Forget asking a few other law offices to use a system like this. It would at best only be useful for him, and then wouldn't track changes properly.
It is common for law students to digest course material into a short-ish (20-30 pages, depending on the class) outline of the material, as a way of studying. With my modified syntax highlighting config, I use different color bars to represent different level headings to make it easy to see how my document or outline is organized.[1] I then have a latex template for pandoc which lets me convert it to a beautiful document that is useful during open-book exams.
Using Sublime as a WYSIWYM editor is much more pleasant, as the editor is far more responsive, than using a WYSIWYG editor (like MS Word). I actually recently wrote a paper for class entirely in Markdown in Sublime. Pandoc lets you convert markdown to PDF (it uses latex internally), and when you convert to docx format for Microsoft Word, you can use a reference file to define the style formats. It's really easy to write something like a brief or a memo and convert it with a reference file to a format that others can work with, properly styled.
[1]: Here is a screenshot of what my editor looks like: http://i.imgur.com/xU9eSwt.png :)
