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.