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