That's even worse advice than what I was responding to. Great way to anger a high-ranking executive and probably get fired.
Frankly a lot of the advice in this thread seems to be coming from people who are very junior or otherwise don't have experience dealing with high-ranking executives. Heck, even mid-ranking executives would respond very poorly to the kinds of actions advised in this thread.
Here's the situation: a high-ranking person in the company is so powerful that she can disobey IT policy by refusing to update her computer. This person is also powerful enough to demand that changes be made to a corporate website to make it compatible with her older computer. This is a problem for the head of IT, and the head of IT either lost that battle or decided it was not worth fighting.
This is not the right place for a more junior IT person or developer to stick their nose in by going directly to that executive with some bogus "liability waiver" or appeals to wasted money or whatever else. It won't go well, and it's wrong to do it in the first place because it bypasses layers of management and the historical and political context that led to this outcome. If the head of IT couldn't solve this problem, a stunt like what you are suggesting won't solve it either.
I get what you're saying, and I think that most corporate IT departments run themselves as little fiefdoms with false pretensions of importance and power. But if someone is insisting upon running systems that don't conform to reasonable standards of the company, then something needs to be done. I would consider requiring that device to be isolated from the network with a small firewall.
But the waiver is a good idea—though unlike your assumption that it would be handled by an junior, such matters ought to be sent up the chain to the CIO or equivalent, and it should be the responsibility of the CIO to get the signature or take personal responsibility themselves.
Either you make progress or get... encouragement to go find a better job. Sounds like a win-win to me.
This assumes one has a job where you can easily replace it with an equivalent. Even in IT, this is not the norm outside of a few limited areas and fields. Most people have to worry about keeping jobs that arent perfect.
Frankly, this is the kind of "if it were me Id just be an asshole because being right is the only thing that matters, just don't look at my actual life actions" advice I got from my grandfather growing up and just sounds very unaware and privileged today.
Does it suck? Yes. Is there some act this person can do to change things? Maybe. Are there a lot of actions that can feel morally justified but arent, and are also really bad ideas to attempt? Oh my yes.
Do I think you are offering this terrible advice? Cant say...there's a lot of context we can be assuming differently. I can say that I dont see the take away from many of the messages on this thread being terribly helpful.
Sometimes you need to break the chain of command (either from below or from above) to get things fixed, otherwise some problematic people never called on their shit and the whole organization suffers.