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I believed that law was a sluggish, tech-averse industry when I signed up to join it. But I don't see it living up to its tech-resistant reputation. It's very easy to blame the customer that way, when you have something to sell. As a lawyer, a coder, and legal toolmaker, I've been there. But my lived and observed experience of practice is that lawyers adopt what makes them competitive.

As a result, they've often been early, broad adopters of general-purpose office and productivity technology. Sometimes to their eventual detriment overall, by standardizing on an early generation at the expense of later incremental improvements. But at the same time, I think US lawyers as a class are remarkably resistant to whiz-bang pitches of especially law-specific solutions. It's easy to sell a lawyer some technology that their counterparts are using to run circles around them. It's hard to sell a lawyer some technology with a change-the-world, techno-solutionist pep talk.

Anecdotally, I can't say how many times I've attended or watched pitches by tech-focused people, business managers, or technophile lawyers with very little practice experience hocking half-baked solutions held up as replacing or supplanting lawyers in some way. My reliable takeaway from those pitches is that the founders don't know what lawyers do. When I ask about tablet ownership, cloud service adoption, security standards, terms of use for professional ethics requirements, or Lexis terminals in the 60s and 70s, it's usually a big, blank stare.




It’s vital that tech for professional services empower the professionals. I do think venture capital fails in this regard - don’t start with “disrupting law,” start with empowering it, which may be a lifestyle business at first but very possibly a sustainable one. Then look to scale from there. Not sexy, but it’s how I think the market will be cracked.

Whoever can build tooling to help lawyers decipher a 100 page credit agreement in half the time, reliably all the time... will do way better than someone replacing those lawyers with AI-outsource hybrids that can do it in 1/10 the time, but only succeed half the time.


Nice writeup. Too many startups and founders out there w/ no idea about the industry. Thus, excuses of the type you mention ("sluggish, tech-averse, etc") predominate over critical evaluation of the extremely sticky and complicated obstacles to new innovations in the legal tech space.

That said, as a fellow lawyer, coder, and legal toolmaker, I'd posit there's more of a middle ground than you laid out:

> It's easy to sell a lawyer some technology that their counterparts are using to run circles around them.

Of course – it should be easy to sell lawyers on established technologies! In fact, one could argue competence REQUIRES lawyers/firms to adopt said technologies. It's not wrong to be disappointed with what's being defined as tech adoption in this thread by industry defenders:

> security standards, word processing, LANs, spreadsheets, aggregating data & metrics, owning an iPad, ...

These are bare minimums and best practices in every other industry, and celebrating attorneys for meeting an extremely low bar is no better than technobabble.

> It's hard to sell a lawyer some technology with a change-the-world, techno-solutionist pep talk.

Stipulating there's a difference between snake oil and actually meaningful legal-specific technologies for practicing attorneys/firms, then yes, certain players in the industry will be more conservative about adopting new innovation. Conversely, a functioning market would also imply the opposite: those who responsibly bet on the next big thing, whether in an operational capacity, to drive costs down, or with the consent of their clients.

Sad to say, that's not the current state of the legal industry. Sure, I'm likely biased since I'm still on the vendor side irrespective of how much we aim to make well-built software with solid UIX focused on the practitioner. Nonetheless, firms remain extremely risk averse, hierarchical, obsessed with profits per partner above all else, and long live the billable hour.

Once again, it's complicated, and no one really has the nuance or all the answers, so we all fall back to a bit of a stereotype which makes that middle ground elusive. Ultimately, however, it's really the industry that suffers, and I wonder if/when it will ever change, what the impetus will be, and if it truly requires another global economic meltdown to shake things up.


>>long live the billable hour

Such an interesting statement! What do you mean by it?


Well, from what I understand, (aside from the most standard of legal issues which are billed as a flat-rate,) lawyers bill clients at an usually-eye-wateringly-high hourly rate for any work done in the course of working on your case.

Say a new technology allows lawyers to do the same tasks in half the time it used to take them. That sounds like it rhymes with "half the pay for the same work" to me, which might account for some of the new-tech skepticism.

That's my take anyway. I suppose it's similar to the knee-jerk reflex to automation, where you're liable to 'automate yourself our of a job.'


This has been my experience as well. I used to work at a research group that was hired by law firms to build new tools and products to assist law firms in doing their jobs. Some of the firms I worked with were had custom machine learning based text classification & extraction tools that were written in the early 2000s; long before this kind of technology mainstream.

Obviously the legal field is very diverse. I'm sure there are 80 year old lawyers out there still using teletype terminals to do their work because that's what they know. But my experience with larger law firms is that they see technological innovation as a key to their success.


I’m curious to know what firms you’ve practiced at that weren’t tech-sluggish. Were they run by 55+ partners, or younger folks?


I'm a "transactional lawyer" who negotiates contracts, forms companies, handles regulatory issues, and advises on strategy. That's as opposed to a "litigator" who handles court cases. But I've actually seen practitioners outside my own specialty who've integrated newer technology much more deeply. Automated case assessment in some immigration practices, for example.

In my experience, there is some correlation between technology and age. But keep in mind that 55 year old lawyers were born in 1965, started coming out of law schools in the late 1980s, and became established in the early Internet era, before the bubble burst.

Part of what you're getting at might be down to how the role of older lawyers tends to change, especially in firms. I would say most older lawyers in transactional fields do far more advisory and strategic work, akin to consulting or even lobbying, than issue research, contract review, or routine drafting. If the senior partner's working pretty old school, but all the junior partners, associates, secretaries, and paralegals under them use their own tools, that's still a pretty newfangled picture, overall.

Part of it may also be certain specialties that deal routinely with government bodies, like court systems and regulators, with their own adoption curves. But don't jump to conclusions there based on standards for consumer technology. The websites may look clunky, and the interfaces may be pretty retro. But the databases involved are often functionally complete, resilient, and workable for the severely outnumbered public servants that use them most.


I made tools to automate parts of my Canadian immigration practice, (as a non-lawyer, licensed legal services provider), but that was only increasing my profit and ability to scale. What I really got paid for was perceiving what the customer wanted, and matching that with what they could endure / afford / likely become eligible to do, while reassuring them they could still be happy. This part could not be automated.


The point about govt systems with clunky interfaces is a good one.

I think one area that we need to improve on is handling of PDFs. It's clearly the standard for documents of record. However, the fact it can be scanned images or text data is inconvenient.


Perkins Coie.

Well known clients include msft/uber. Bitcoin/cryptocurrency practice is well regarded.

I think being close to a lot of tech clients helps. We get some flack for shunning slack/teams/gchat4business/stride/chime or wtf amazon uses/workplace by fb/etc and relying on “antiquated” email. We definitely prefer to work more in thoughtfully composed emails compared to a fluid team chat. It’s also easier to organize and manage.

However, I’ve been pleased with my colleagues ability to ask relatively smart questions about ML. For example, people are pretty good at responding to ML hand wavey bullshit with specific questions about training data, labeling, features, model architecture, etc.

IMO, we have some younger, eg 40-50, people in leadership positions in my practice group.


"Our clients depend on our ability to receive their messages reliably and respond efficiently. We can't settle for less than decentralized, asynchronous communications over standardized open protocols."

Just be advised that if the prospect's head actually explodes, you may face capacity challenges to your engagement letter when you bill.


That’s a good way to phrase the advantages of email


One of the most impressive tech lawyers I’ve met is a corporate Perkins guy, so I can believe it.

I actually used to work in their Palo Alto office — back when it belonged to MWE in 2007-2009. The new lobby that Perkins built is much nicer!


Thank you for this detailed write up, it mirrors my experiences.




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