My experience is that more often the engineer knows the good reasons to upgrade but doesn't know how to articulate them to you, especially when you are known to be hostile to the idea of upgrading things.

I've experienced both extremes and everything in between, and I don't know that there is any consistent good or bad actor in these situations. Everybody has their own goals and it's human nature to overvalue the things that you care about and undervalue the things that other people care about. Good organizations are set up such that everybody can be a little biased in their priorities but the organization as a whole ends up going down the right path even if no one person is 100% right about what should be done. The decision-making in bad organizations often follows from one type of person with one set of biases making all the decisions. I don't blame people for having biases, I only blame people for denying that they have them and not trying to understand other points of view.

However, I can say for sure that there is a widely held view among professionals of all backgrounds (business, technical, whatever) that if someone fundamentally doesn't know how to articulate their point to someone else with a different background or set of priorities, then that person hasn't thought enough about why they should do the thing that they're pushing to do, and that there's a high probability that they're just doing the "overvalue the things you care about/undervalue the things other people care about" cognitive bias that everybody tends to do naturally.

I don't know if that's a good rule of thumb or not. There's at least some truth to it. But whenever I'm in a situation where I feel like someone isn't going along with me because I don't know how to articulate my point to them, my first thought is that maybe I need to think about it some more. I don't jump to thinking it's their fault because they don't speak my language.

This is a great comment and I totally agree both that there is almost never an actual "bad actor" and that being able to articulate a persuasive argument is highly valued in decision making. Maybe it is even a decent rule of thumb for coming to decisions under the inevitably imperfect conditions of the real world, but I do think that there are people who are just legitimately poor at articulating things, not because they are wrong or haven't thought things through enough, but simply because they are bad explainers, and that those people tend to be unfortunately undervalued.

Actually, I am an engineer, and I myself try to keep up with new technologies. But that doesn't mean I will use them just because they are new - in my mind that is additional risk. I have used my share of technologies which were made obsolete anyway, and it's no fun converting your codebase. But I guess the cool junior engineer who went to another company and left her old company taking care of her project using not-new-anymore / obsolete technology, doesn't care much about that. But I guess if she can't articulate why her newest technology stack is better, we should just switch?</rant>