It’s not wise to be against the direction of an executive. You will be labeled combative, misaligned, or even uncooperative. It’s not worth it. Unless you have a strong political ally, it can be career suicide in your company.
It also really depends on whether you pick your battles or not. If an engineer complains every detail of a system then you get a "boy who cried wolf" effect at some point.
Well, this is one of the major sources of the problem, isn't it? Executives who can't accept someone disagreeing with their Glorious Vision, like they're prophets or geniuses whose thoughts we mere mortals could never possibly understand or equal?
We've accepted the idea that being at the top of the org chart means you're treated as a petty king for far too long. Not only is it terrible for the people under them, it's also straight-up bad leadership: it's guaranteed to lead to worse results than being able to graciously accept feedback, even if you don't actually change anything because of it 95% of the time.
You need to know how the person behaves and how to approach them. Some people will take very badly to be 'challenged' by a subordinate in public but may have no issue if you make a 'suggestion' in private.