Sure, there are a few things. That's why I qualified my statement. But they're necessarily going to be minor things, not the larger persistent problems that only become clear once you've spent some real time working.
no, a CEO isn't going to know what a clopen is like, but if they're responsible for people who are designing a process / choosing a set of tools / setting expectations for employees, being willing to step into the workers' shoes is a worthwile move.