I don’t know much about IT (I’m CS), but Ad is very specific to Windows, no? Shouldn’t you instead be asking them about higher-level concepts like access controls, networking principles (http vs tcp vs ip, routing, dns, etc), and basics of cybersecurity (attack surface, network segmentation, etc)? It sounds like you’re looking for practical knowledge about specific solutions rather than familiarity with concepts.

in CS, I can’t expect someone to know our specific stack, but I can expect them to know foundational principles, like data structures, algorithmic complexity, design patterns, design principles, etc. So unless they express familiarity w/ our stack, I keep the questions theoretical, and even if they are familiar w/ our stack, I still keep the questions high level (i.e. for Python, I’ll ask “gotchas” like what’s the difference between a list comprehension and traditional iteration, how does Python’s threading work, etc). I expect them to need to learn something in the first month or two, but also to largely learn on their own. Learning our stack when you’re comfortable with programming in general isn’t all that difficult, learning our stack when you struggle with basic concepts will be a challenge though.