One of my pet peeves is documents written for clients in bureaucratic language that even I have to read two or three times to comprehend (sometimes never comprehending at all). This is usually accompanied by complaints from the case manager that the client didn't do what was laid out in "The Plan." Infrequently do they ask, "Am I making the instructions clear for the reader?"
There are now a number of good Readability Utilities online. I use this one. Just simply cut and paste your text...it will tell you what grade level the reader must have in order to understand what you've written. It will also flag difficult sentances and $10 words so you can see how to craft a better document.
This is not asking you to 'dumb down' your writing, but to recraft your words to make it easier for the reader to understand what you're trying to say. In the mid-80s I sat in a media symposium where New York Times editor Turner Catledge was explaining his decision to reduce the paper's comprehension level from 12 grade to 9th grade. His point was that even highly educated people absorb more information when writing is basic.
So go to Online-Utility.org and paste in something you've recently written. Then post in comments to tell us what you learned.