Sometimes too many people are too invested in the crazed/idiosyncratic way of doing things... and unless the humans can be convinced to fundamentally change their process, adding software will only give you... well, craziness with a computer.

This is a superb line and I will be stealing it.

We keep resisting though, and most of the time we get them to come around and thanking us later for the push-back and helping them evolve.

Technical people have a really bad habit of solving for theory rather than practice and they develop this attitude that those who are seemingly entering into odd behavior are just not as good or smart as them.

True, but "actual" is a rather low bar. I once worked at a company where a big internal enterprise app controlled a lot of operations, and saw that many of the layers of cruft in the app were because it became the preferred battleground of corporate dysfunction.

One example is that the sales team kept closing deals ('cuz commissions) which were difficult to fulfill, unprofitable, or cannibalized from other assets and activity.

This lead to repeated and increasingly obtuse layers of code for estimating gross-margins, showing values at different interfaces and steps and warning styles, managing and modeling gross-margin reporter/reportee connections and automated alerts and permissions systems where they system would block certain people while e-mailing other people for clicking approval boxes, etc.

There's a doctor further up this chain who states they preferred paper.

I wouldn't say that, most devs who've worked with product requirements and users have seen issues with users wanting something inefficient or illogical, basically because they don't like change and/or don't understand why they are doing something.

When we try to automate part of a person's work, we have to encourage the person to take a look at themselves and the way they do their work. This is not easy for people! A lot of times we're asking someone to admit that they don't actually know why something is done a particular way. Or we point out that they are doing the work of another person in another department. And, all the time, this person is worried that at the end they will be replaced by software and lose their job.

I think it's really hard to get to a place where everyone is comfortable enough to be frank about what they do, what the software might be able to do, and what makes sense.