Why does this happen? It’s obvious. Every high-tech company has people called “Product Managers” (PMs) whose job it is to work with customers and management and engineers to define what products should do. No PM in history has ever said “This seems to be working pretty well, let’s leave it the way it is.” Because that’s not bold. That’s not visionary. That doesn’t get you promoted
The evidence suggests that for mass-market products used by on the order of 10⁷ people, it’s really difficult to predict which changes will be experienced as stupid, broken, and insulting.
Harsh — but, as someone on the receiving end of these kinds of changes, it often feels true. These changes can sometimes be well-intentioned and constructive, but they are delivered at a rapid-fire pace that is disorientating. Users do not want to learn and re-learn software; they — we — want to edit photos, or browse the web, or send an email. By making workflow-breaking UI changes, software vendors are effectively punishing users for their loyalty.
That is not to imply that things cannot change. The beauty of software is that it can be updated and iterated-upon, and high-speed internet connections mean that updates can be installed without shipping a whole new disk. But the prevalence of automatic updates and the software-as-a-service model means that users have lost information about what will change before they update, and have little control over when a new version is installed. Some vendors have adjusted to this by adding first-run tutorials, but that is not a substitute for making fewer and more careful changes.