Resources for Learning to Get to the Point
“Getting to the Point” in communication is an art. I don’t know any book or course that truly explains it. I think there are three parts to developing the skill.
First, you need to know your purpose in the conversation. This involves knowing what you want to get out of it, and also what the other person wants to get out of it. The best book I know for clarifying this issue is, Getting Through to People by Jesse Nirenberg. It has great ideas but it is out of print. (Women--you'll need to overlook the fact he writes to men, not women. It's one of only two books I've ever read that seemed to do that.)
Second, you need to know how to condense a complex thought into its essence. At some level, you can do this if you ask yourself to put the thought in one sentence. But if your sentence is still long and complicated, you need more practice formulating clear sentences. This is something you can learn by practice.
The best book I've found to practice this is Joseph Williams Style: Ten Lessons in Clarity and Grace, which includes exercises. (He also has a version without exercises, called Style: Toward Clarity and Grace.) Although this book is on writing in general, a lot of space is devoted to making individual sentences clear and direct. His biggest tip: make the grammar match the action. So, put the agent as the subject of the sentence, and put the action as the verb.
(If that amount of grammar is too complicated for you, I recommend doing the exercises in Rex Barks: Diagramming Sentences made Easy by Phyllis Davenport.)
I teach this skill in my self-study course “Condensation.” This is a skill for extracting the main points and theme from a piece of writing. It is available for members of the Thinking Lab.
Third and finally, you need to notice during the conversation that it's time to get to the point--and then "one-sentence" your thought or use the "pyramid" technique. This may require you change long habits of speech!
The best way to practice this is to join a Toastmasters club. (http://www.toastmasters.org) These clubs are all over, and each meeting has a section called "Table Topics" in which you are asked a question and give an extemporaneous 1-2 minute answer. Every time you do this, you get a chance to practice "getting to the point" at that moment.
I hope this doesn't make "Getting to the Point" sound ridiculously complicated. Like most skills, the best way to get better is by trying to do your best and learning from experience. Books help-- but only if you have been trying on your own and can read the book in light of your firsthand experience.