Why would you? He’s literally the only person ostensibly in charge of the direction of the company. Destroying the company through a security exemption or a bad business deal - both are the leader making a poor decision due directly to his seat of power.

Give sound advice of course, but ultimately it’s the exec’s decision make.

I have never worked in a company where an obviously incorrect CEO-demanded security exemption (like this one) would have been allowed to pass. Professionalism, boards (with a mandatory employee member/representative, after some size) and ethics exist.

30 years in about 8 software companies, Northern Europe. Often startups. Between 4 to 600 people. When they grow large the work often turns boring, so it's time to find something smaller again.

Been there. The CEO of an internet security company was the one who clicked on the wrong email attachment and turned a virus loose.

I mean, I don't know if he had a security exemption, or if anyone who clicked on it would have infected us. But he was the weak link, at least in that instance.