There’s one kind of permission prompt that always really throws me off and interrupts my workflow.
It’s the one that forces you to go into System Preferences, unlock the specific preference screen by confirming your account password, then enable a checkbox and on top of that restart the whole app you just allowed the access for. I really get annoyed every time I get this prompt because I know it’ll take me 5 clicks, one password prompt and one app restart to continue my work.
Most of the time it’s for something mundane like “Let this color picker read your screen” or “Allow this FTP app to read your local files”. In some sense that probably is reasonable for some users but there should be a pro-mode to disable all these if you know what you are doing (not downloading random apps from the internet). The whole workflow to allow this is also pretty confusing and for some non-technical users probably even a barrier.
I upgraded to Catalina pretty early on and didn’t have that many problems with it (most of them are documented on this blog), after the initial phase of clicking on “Allow” for a few hours it’s basically like the macOS you are used (for better or worse) to but that one is still very disruptive.