Thinking like a CIO/CEO/or manager should change your job. Think about their point of view, their needs, etc. and it will help you. You don't have to agree with them, but understand them.

I think you ought to support your boss, while politely disagreeing, or being able to argue with them. But when the decision is made, support them. I think it's the same with government. You can disagree, you can protest, but you have to support them as our leaders.