Having a Point
There are some skills that people self-identify they need. And there are others that they don't.
Many people who have a problem getting to the point don't realize it. But when you talk with them, you see their problem reflected in your own frustration. They say something, you try to clarify. They neither agree nor disagree, but sheer off onto another topic. You ask them a question. The answer doesn't address the question. The conversation rambles and digresses and circles around, and you can't pin them down.
Now, sometimes this is deliberate evasiveness, but that is not usually the case. Usually the problem is that they don't know how to get to the point.
This is a skill that I had to learn consciously, so I am aware, both of how surprising it is to realize you are not, in fact, communicating well, and what is needed to communicate better. There are a number of best practices, but the crucial prerequisite is to have a point.
All three words are crucial.
First, you need to have a point. Many times people come into conversation without a clear purpose. They do not know what they want to say, or even why they are having the conversation. It is impossible to get to the point if you don't know what it is--you can't aim for a destination until it's been identified.
This is why you need to spend at least a moment figuring out why you are having a conversation. If your purpose is to convince the other person of something, you need to know what you are trying to convince them of--you need to identify the point.
On the other hand, if your purpose is to pass the time, or to explore issues, there may not be a point to communicate--and then you need to make sure you don't give them reason to believe there is. If you are just exploring and playing devil's advocate, but you're acting as if you are trying to convince them of something, they may both confused and frustrated.
Second, in order to get to the point, you need to have one point. One point. If you have multiple points, you need to make them one at a time--and wait until you've gotten one across before going on to the next. If you try to make several points at once, the other person will likely not be able to follow you.
Third, the point needs to be a point. A point is a single thought--one complete sentence--which is the conclusion you are trying to get them to reach. You may give examples to concretize the point, you may make an argument to prove the point, you may give contrasting cases to differentiate the point. But whatever you do, whatever you say, it needs to be logically connected to validating the point. You may address their concerns by clarifying the points. You may say a lot of things, but if you want to get to the point, everything you say needs to add up logically to the one point--the conclusion that you are trying to get across.
When everything adds up, a pyramid becomes a great metaphor for the conversation. You build a layers of evidence on a base, narrowing to the point.
But if you include the kitchen sink and anything else that occurs to you along with logical material, you get a pile, not a point.