Two-way communications

Jeremy had an interesting post about the difference between writing and explaining, which he sees as two sometimes separate topics. I’ve had the same experience he describes: it’s usually easier to explain something in a conversational way (even if it’s via email or IM) than it is to sit down and write an explanation from scratch. When you’re writing, you don’t have the same information about your audience’s assumptions and knowledge that you do when you’re standing next to someone at the whiteboard.
My solution has been twofold. First, I tend to write like I talk; one consistent comment I’ve gotten from readers of my books and columns is that they like my conversational style (although I do have to write less conversationally for more formal audiences). The other is to treat my writing like a conversation; at least for books, I actively try to find volunteer reviewers with a wide range of experience levels, then I push them to give me good feedback. This helps a great deal, especially if you can find people to bounce ideas off as you go. It helps if you’re really familiar with your audience and the things they want to know, which is why I spend so much time talking to Exchange and Windows administrators in the larger community.
Of course, neither of these approaches actually helps you get the stupid writing done in the first place. For that, I recommend Heinlein’s Five Rules, as amended by Robert Sawyer.