In conversation, I used to think it was good to say what you meant. I thought doing so would help me be understood. But I learned very quickly when tutoring computer science students in college that this strategy does not work in general.
The real challenge is to say what you think will make you understood. This turns out to be hard, because you need to develop a mental model of another person’s understanding. It means looking at what you’re trying to say in a new way. This has happy side effects, though: it makes you more empathetic toward others, and gives you a better understanding of the subject.
The old joke “Those who can’t do, teach” is a stupid statement—but an awesome prescription! If you can’t do it, teach it! By explaining things you’ve learned to others, you can develop your understanding and skill. When you can explain something to anyone, it means you have a fully developed model of it in your mind, one that you can look at from anyone’s point of view.
Similarly, when we’re trying to understand others, we should not be listening to what they say but trying to understand what they mean. When someone says something offensive or upsetting, often they didn’t intend for it to sound that way, and the intent matters. Being misunderstood feels bad; think about how often you’ve probably made someone feel that way because you didn’t take a moment to think.
As listeners, we should ask for clarification and try to understand why something was said. Sometimes it’s because a person has a belief we disagree with, or a bias we think is unfair. Sometimes it’s because we were hurtful to them, and they were acting in self-defense. In these cases we can use the moment as an opportunity to learn and teach, rather than getting offended and putting everyone involved on the defensive.
The vast majority of the time, people are basically well-intentioned and just trip a little on the delivery. Giving them the benefit of the doubt is important to develop mutual understanding.