Microsoft Word apparently has a feature where you can check for grammar and be assigned a Flesch Kincaid Readability Score. It uses a sophisticated algorithm to measure how smart your writing is, essentially. The more syllables per word you use, and the more words per sentence you use, the lower your Readability score is and the higher your Grade Level Score is. Apparently government and insurance forms have very specific requirements on what score they pull down.
That's not a very awesome way to assess that kind of thing. Hemingway would score abnormally low, for instance. I have a sneaking suspicion that somewhere in Cuba there's a man who never got his due for writing large chunks of "Old Man and the Sea" when he was in fourth grade. On the other end of the spectrum, philosophers like Sartre and Kierkegaard got incredibly dense to say some pretty basic things.
If you write a piece of fiction and have a computer tell you that it's actually written at about an eigth grade level, you tend to get a little defensive. It's natural. You know what would really show a high level of writing intelligence? Semicolons. Them things is crazy. Think about it: whenever you see someone use one and you assume it's used properly, you automatically think higher of that writer. I'm still not sure I know exactly when to use a semicolon, but I'm lacing them all over the place until someone tells me I'm wrong.