should have known IE the person is operating in a subject/domain where they're expected to know certain things, regardless of their own experience, like deep se

should have known IE the person is operating in a subject/domain where they're expected to know certain things, regardless of their own experience, like deep sea diving based on communique both to and from the CEO, the CEO did, in fact, know, that the vessel was not certified to do what it was doing, and that there were safety risks to it