This is really the crux of it: senior management needs to take the lead setting up policies which are efficient enough not encourage people to try to bypass them and the culture that everyone in the company should feel comfortable telling the CEO “I’m not allowed to do that”. This is possible but it has to be actively cultivated.
Let’s not ascribe too much power to those, either: NSLs can compel release of certain types of information but they can’t force you to do things like transfer money or even disclose the contents of private messages.
Good luck with that.
I've had a CFO that didn't talk to tech people except through proxy have a "tell your mom to pass the potatoes" style meeting with his secretary as medium. Yes I stood there he talked to his secretary and repeated what each of us said 5 feet away from each other. This was a large bank.
I've had a general council yell with spittle at me because I suggested that it was probably a bad thing that the IT Dept was effectively acting as power of attorney for the company by doing digital signing for him and he should probably learn how to do it himself for legal reasons.
If they can throw you under a bus because you raise a valid issue, what are the chances they'll protect you when some fraud paperwork gets signed by the IT dept (so you).
Very few CEOs are going to make people feel comfortable telling them no.
My anecdotes were to illustrate its widespread if I've personally encountered it multiple times. Also just to entertain.
If you refuse and it's an actual emergency with the real CFO, it might be a career limiting move, if you don't get fired.
If you accept, it might be a deepfake CFO and you might get sued.