I am finding that the difficulty I have expressing my ideas is making it more difficult than it should be to work with other people, even other developers. How can I learn to express my thoughts and ideas clearly and concisely?
I think one thing to try would be to not ask on SO.
Having said that, if the problem has persisited since childhood, you should consider seeing a doctor about it. It could be related to sleep disorders, depression, or even a speech disorder.
Be sure not to assume that these are the causes: let the doctor determine whether or not they are.
However, contrary to much popular opinion, many things that we have historically considered to be "personality traits" actually do, in some cases, have a physiological basis. These should be thought of in the same way we think of any purely "physical" issue, with the same standards of proof, and of treatment.
Take a technical writing course, or any writing course, if you can't find one on technical writing. You can find some links to tips for technical writing here. I think you'll find that if you improve your writing, you'll also improve your other communication skills.
These solutions won't work for everyone, and you won't need them forever, but they're a start.
- Always write it out first
This may seem a little pointless when you've just got a quick one off question, but sometimes it will answer your own question for you. Even if it doesn't, once it has been written down, you can check it yourself and try to look for areas that might be unclear or a little vague to you. If a section is even a little foggy to you (the person who wrote it) then it's almost guaranteed to be absolute gibberish to someone else.
- Try Using Diagrams
Obviously this depends on the type of concept that you are trying to articulate, but many people respond very strongly to a visual representation of what they are trying to learn. You might also find it easier yourself to articulate your thoughts in relation to a visual diagram of them. Things that seem very obscure when discussed orally become very clear when you relate them to an interconnected diagram. This works well when you are discussing the architecture of a multi-layered enterprize system. There are usually too many parts to do anything WITHOUT diagrams.
- Use Examples (or analogies)
The more examples you use, the more chances your target has of understanding you. To use an analogy, if your goal is to climb onto a roof with a ladder, it doesn't matter if they land on every rung of the ladder, but they have to hit enough of them to get to the top. So, even if the person might not understand what you mean initially, if they understand your example then your earlier comments will make more sense. Even if they get lost, the example gives them an opportunity to get back onboard with what you are talking about.
- Practice
Start writing more often if possible. Instead of talking to someone over and over until they understand, or repeatedly going to the one person who understands, try writing it out in an email to them instead. Another option would be if you have a company newsletter, try to write some pieces for that. You'll find that after reading what you wrote, (a couple of months later) there are certain things you do in your writing that really anger you. I myself use a lot of commas, and it really bothers me when I read it later.
Ultimately, practice is probably the most important one. If you are only trying to articulate yourself in the 5-10 minutes a day when you NEED to, then you'll find that you aren't really getting any better. But if you focusing on articulating every technical problem you come across as if you had to describe it to someone else on your team, then I think you'll see some improvement almost immediately.
I have a few more, but I need to think about them first =)
You need direct, immediate, well-qualified feedback. Do either or both of:
Engage someone who is in some way a professional as regards the English language: an English teacher, a professional speaker, a writing instructor -- keeping in mind that the written and spoken mediums are very different, and many who are very good with one are terrible with the other.
Take a class or join an organization or club that makes excellent speaking or writing part of what it does. I've heard great things about Toastmasters International, but don't know much about it. If you take a class, make sure that it is interactive, not just lecture and assignment.
More postings on boards like these will not help you. You need live critics. Find a pro or a group and get immersed.
Writing for Wikipedia helped me a lot in refining my style. Nowadays, in the professional emails I send, I try to make the first sentence a summary of my main point, just like the first sentence of an article has to summarize the rest of the text.
I which more people who do that, I'm plagued by email asking me to fix something, which require me to read two paragraph to discover the point.
The page http://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style is a good starting point.