Nothing good can come of it

When I am helping a friend or colleague prepare for a confrontation with  a coworker, boss, family member or similar individual, I often ask the same question:

What is your expectation for a reasonable outcome?

For example, if you know that your supervisor has strong, seemingly unwavering feelings about a decision that he has made, but you disagree with that decision, is it reasonable to expect that you will be able to change his mind or alter the way he makes decisions in the future by...