Always excellent, Madison! With so many of these points, it's so often a focus on 'oughtness' and not, necessarily, what actually happens in organizations. For the first time in decades, I'm finally, starting to see these multi-generations come to the same table to have the same conversation — but it's not always inherent.
That's the reason my recommendation to the Z-er was not that we shouldn't use the program. Rather, that we need to talk with the whole company to figure out what everyone needs and how the program can meet those needs. It's a slightly longer road (and that can be frustrating for people who simply want to pull the switch and make the change) but it's one that is far more fruitful.
That builds not only technological competence, it also builds organizational competence and helps fan budding culture.
So often when we talk about "a thing" (program, process, etc.) it's not actually the thing we're talking about — the scope can (and should) often be so much wider.
And while I bet the legal field is slow on the tech uptick, I can assure you my nonprofit space (as a whole) is often woefully behind the curve!