When trying to get something changed, a brick wall of technobabble is presented to school management who generally don't know any better and defer to this 'higher power'. Unfortunately I know enough to have seen through many such reasons (such as "You can't have more than 10 Apple devices on a Wi-Fi network, it will crawl to a halt", and "Firefox? I'm not having that rubbish on my network - we're sticking with Internet Explorer"), but there's no way to convince anyone in management that they're being sold a dummy, particularly when it was they who decided to hire the IT manager in the first place. I've got a room of machines where it takes 5 minutes to run the software I use to teach (Cubase) because the machines have mandatory profiles enforced that have been taken before the plug-in scanning has been done, so it does this scan (5 minutes or so) every time you run it. Think of the learning time lost over the 5 years that's been in place.
I really think a plan of getting these people out of their offices and into the workplace to shadow people who use what they maintain would make a world of difference. Instead of being some whiner who creates 'frivolous' support requests, they would see that a bad decision can drastically impact the experience of everyone who uses their tools. I think I say this as someone who has been on the other side of the fence; I do support for some IT installations (including a first school with 400 pupils), so I'm tech savvy enough to be able to do what's needed, but try to approach it from a function-first rather than ideological approach.
The more this gets filtered through layers of communication and management, the worse the software will be to use.
Making the programmers understand the subject area on their own also has a benefit, but it seems a far more costly way.
Talking directly with the users is fine. But if that is your sole input, something is probably broken.
In particular, I'd like more training on law and finance. For some reason, I have never seen any lawyers or accountants being eager to teach me about interpreting laws, or balancing books.
If you're Stripe, that's coding, APIs, and finance/payments (that last is the bit engineers should be taught).
If you're Google, that's ads and ad-buying - hence the company practice of giving engineers (and maybe other employees?) some free ad credits so they can see what the customer perspective looks like.
Maybe that is just anecdotal evidence but I have found that engineers are often far more open and confident about learning new things in a totally different domains than other specialties.