I think there's space for a middle ground.

Word and Outlook are defacto business tools for sharing legal documentation but oftentimes they are blunt instruments. I see mistakes or delays due to poor tooling all the time. E.g. the wrong versions are emailed, or each party's attorney makes their changes into a different copy of the document, the document becomes corrupted and needs to be copy-typed (I've never gotten to the bottom of what corrupts a document, other than to note it seems to be related to heavy commenting and track changes), or even just unproductive time needing to make simple updates across tens of files.

A github equivalent for lawyers would be fantastic. In fact I think it could be a killer app for the legal industry if it were possible to convince a quorum of big firms to move to it. Think: issue logging per substantive issue; pull requests for changes linked to each issue; full history of each lawyer's changes etc. Roll in some IDE for contact drafting with syntax highlighting, hinting, automated refractoring etc. All these technologies would be just as useful for lawyers as they are for developers.

For what it’s worth, I agree. I’m a junior lawyer at a big corporate law firm in NZ and it’s incredible that we don’t have anything resembling Github or meaningful source control.

If a small team of developers were to build a simple web app the way lawyers draft legal documents, it would look like this:

1. Developer 1 writes up the initial JS, CSS, and HTML files and emails them as an attachment to Developer 2.

2. Developer 2 prints out the files, edits them via hand markups, sends the printouts to his secretary to mark up electronically, and then emails the files to Developer 3.

3. Developer 3 repeats step 2 but emails the files back to Developer 1.

4. During this whole process, while one developer is working on the app, the other developers are waiting idly - even if they could be working on a separate part of the app with no risk of conflict.

This is a simplified explanation and lawyers will have some degree of version control internally through software like i-manage, but I find it hard to believe this process couldn't be improved significantly. I’ve been seriously considering starting a company in this space.

The premise that the other team members could be working in the documents at the same time is false. I’m a litigator, so that’s a bit different, but there’s almost never a situation where I want other people editing the document while I’m doing so, even if the technology permitted the changes to be integrated seamlessly.

Is this inherent to the way law works, or did practices develop this way to route around the messiness of simultaneous changes without git?

It’s inherent to the way writing prose works. Documents are sequential, not modular. You can’t have 10 people all working on a novel at the same time. Maybe there are a few logical sections you can split up, but even then everything needs to be in the same voice so someone needs to massage the pieces during integration. Automatic merging provides little benefit over copying and pasting a couple of individual sections together. There are also very few documents being written. (The ratio of documents read to documents written is probably 100:1 between cases, discovery documents, etc.) You’re never editing dozens of files at the same time. Maybe 3-4, and often just one.

Right now I’m working on a 100 page due diligence report. Even if I’m doing a simple task like proofreading, I have to mark up my changes by hand and wait for the document to become available to access because an associate is making edits to a single page of the report. To make things worse, once we finish our draft, we’ll send this document to our clients, the investment bankers, and the auditors to review and send us 3 different versions of markups. Meanwhile we’ll be continuously updating the document ourselves.

Often it becomes unclear who has edited what and when, and its exacerbated by the fact that many lawyers still prefer to mark-up documents with pen and paper and have them updated later by their secretary (while in the meantime the document will have gone through another round of markups from other lawyers in the team).

I don’t know if an automatic merge is the right solution either, but I can absolutely see the value in software that helps manage this mess. I realise it might be different in litigation, because in this case we’re not trying to draft a coherent legal argument but tick off a series of regulatory checkboxes that are semi-independent from each other.

Perhaps it's a contentious vs non-contentious thing but in the latter (my world) we edit drafts collaboratively all the time.