"The legal profession is undergoing a massive structural shift"

You're 90% of the way to the answer. Take into account Hanlon's Razor and it should become clear.

Unless the people designing the law are smart enough to take into account every single edge case, we're faced with a choice between gross miscarriages of justice through inflexible laws, and gross miscarriages of justice through incompetent or corrupt judges.

We know the people designing the law aren't that smart; and even if they were, the laws are already too complicated. The only solution is to strike a balance between the two types of errors that minimizes their sum.

Fundamentally, law remains a guild system, with the governing licensing restrictions severely limiting the ability to innovate. Only licensed persons can be owners of firms and only licensed persons can provide the key services. No fee-splitting or profit sharing is permitted with any person who is not licensed. Even one who is licensed is limited is performing services other than in the locale for which he is licensed. All of this may be well and good for "maintaining standards," as the bar associations say, but it means this is and will remain a closed profession that remains remote and removed from average people.

This is not a knock on professionalism. A really good lawyer is well worth the price, even at high rates, for many business transactions. But making services broadly affordable remains a challenge. Technology can help as long as the laws bend enough to allow firms to adopt innovative business models taking advantage of it - how far this can go will ultimately depend on the rules of the guild.

After over a decade of doing this, I notice that my clients really want the answer to two questions:

1. What are the market standard terms for the transaction?

2. What did we (i.e., the client) agree to in the past?

In big law firms, the answer to these two questions is all too often locked into silos. Either knowledge of past deals is hidden from software because it's buried in MS format binary files, or it's buried in someone's head. It's quite common to see intraoffice communiqués go out by email: "Has anyone done XYZ for ABC in the past?" You might get a few responses...or none at all. It's very spotty, and not a good way to build institutional knowledge. At some firms, there might be a Sharepoint or Lotus Notes "knowledgebase" (ugh!), but those are often next to useless and involve a lot of manual human overhead to maintain.

When people think of technologies to enable deal law practice, they often go straight for document assembly or document management. Document assembly and templating is a bore, IMO. It's an area that is already too full of competitors who are trying to solve problems that I don't actually have. Since I tend to represent customers, I don't usually get to create the first draft of the contract. I've actually built a custom document repository with some nice features (e.g., email dropboxes, etc.) but that's just housekeeping, IMO. The real magic lies elsewhere...

In my view, the "document-oriented" viewpoint is the wrong way to approach these problems. Instead, law firms and their clients should be looking ways to break down the document barriers and convert contracts into seamless, actionable data.

Litigation, and patent/corporate due diligence are currently ahead of my practice area in this respect. My practice area (commercial transactions) involves a completely different set of problems and skills, and is an emerging market for technology applications. I'm biased, but I think my practice is harder to commoditize than, say, searching through millions of emails to find phrase matches or potentially privileged communications.

Since leaving big law, I've worked with other lawyers to develop systems for extracting and archiving the information we need to answer the two big questions: What did the client do in the past, and what is everybody else in the market doing today?

Other areas where we use/develop technology in ways that big firms can't:

- Task assignment systems for delegating work to non-lawyers or offshore lawyers, while retaining a clear, auditable record of who did what. Think project checklist templates similar to Basecamp, but more focused on our use cases.

- Interfaces to our timekeeping APIs (Harvest and Freshbooks) for custom reporting/visualization on how we spend our time. This helps us accurately quote fixed fees for projects, and surfaces interesting data about role in the contracting process.

It's a really interesting area. If you're involved in it at all, get in touch with me. I love talking about it with people who "get it". I'm a coder and a lawyer, so I'm perpetually stuck in both (and neither) of the two worlds of law and coding.

Please get in touch with me. My firm's homepage should appear in my profile.