Old decisions are invalidated when it's convenient for VPs
I once saw a place which had built up a rather complicated system to keep track of its business. It dealt with customer data and issue tracking and all of this. You'd call it "CRM" today. This system had evolved as it was written by in-house programmers to handle developments inside the company.
They didn't always have that system. A couple of years before that point, they made the conscious decision to build it and switch from some third-party system. Those people who had been around back in those days agreed that the current system was better.
Not surprisingly, there was much wailing from the users.
Then, one day, this one VP who was driving this whole mess asked me something about the topic. I said something that did not make him happy. It was simple enough, and it went like this:
We're using the current solution because of decisions made before. So, what happened? Were those decisions wrong, or did something change, and if so, what changed?
It's easy enough. Only one of them can be right. If you want to move to something new, that implies the current one is wrong. If it's wrong, then why did we go to it in the first place?
If it started off right and then became wrong, how did that happen?
The implication, of course, is that the new one might be what's wrong. It's also possible they don't have a solid reason for wanting to do this change. It might just be resume-padding material along the lines of "look at this huge thing I did!".
It's obscene just how much money was blown on going absolutely nowhere.