Awkward writing makes the reader uncomfortable. It is ungrammatical, unclear, choppy, or just too difficult to follow. One cause of awkward writing is not using your own words. Instead, you rely on the phrases and constructions of the author you are discussing. The resulting mixture of your author's style and your own is almost always awkward. Even if you are describing someone else's views, use your own words. The most general and important cause of awkwardness, however, is simply the failure to revise. Most writers produce awkward sentences the first time around; good writers take the time to review their writing and know how to spot awkwardness and how to eliminate it. You should assume that the first draft of each sentence will have to be fixed up. Writing on a word processor may make this revision easier and less time-consuming. The best way to test for awkwardness is to read your draft out loud. Most people have a better ear than eye, and if it sounds good it will usually read well.
Once you understand something, it is difficult to remember what it was like not to understand it; but you have to do this to get your point across. To write effectively you must put yourself in the reader's shoes. (Pretend that your reader is a friend not in the class rather than the teacher.) The reader cannot read your mind and she hasn't just spent five hours thinking about your topic. So she needs plenty of help. Don't just make your point, explain it. Give an example. Approach it from several angles. Above all, keep your writing concrete, even in as abstract a subject as philosophy, because abstract writing loses the reader. In addition to keeping your reader on board, empathy helps you to figure out what it will take to convince her that what you write is true. You already believe yourself, but your reader needs an argument. Think of yourself as selling your point of view, or as defending yourself in front of a jury.
An essay is not a list of sentences: it has structure. The structure should be obvious to the reader. Write informative introductions and conclusions. The introduction should not only introduce the topic, it should introduce your argument. That means that you should tell the reader what you are going to prove and how you are going to prove it. Unless the introduction gives the reader a clear map of the essay, she is likely to get lost. Be direct and specific. Replace sentences like "Throughout the centuries, the greatest minds have pondered the intractable problem of free will" with "In this essay, I will show that free will is impossible". The conclusion of the essay should tell the reader what has been accomplished and why the struggle was worthwhile. It should remind the reader how the different moves in the body of the essay fit together to form a coherent argument.
Think of your essay as composed of a series of descriptive and argumentative moves. Each major move deserves a paragraph. Generally speaking, a paragraph should start with a transition sentence or a topic sentence. A transition sentence indicates how the paragraph follows from the previous one; a topic sentence says what the paragraph is about. Both types of sentence are really miniature maps. In the middle of a paragraph you may want to give another map, explaining how the move you are making here is connected to others you have made or will make. The order of your paragraphs is crucial. The reader should have a clear sense of development and progress as she reads. Later paragraphs should build on what has come before, and the reader should have a feeling of steady forward motion. To achieve this effect, you must make sure that your sentences hang together. Think about glue. You can get glue from maps, from transition sentences and words, and especially from the logic of your argument.
There is room for originality even when you are out to give an accurate description of someone else's position. You can be original by using your own words, your own explanations, and your own examples. Of course in a critical essay there is much more scope for original work: most of the arguments should be your own. This worries some beginning philosophy students, who think they don't know how to come up with their own arguments. Do not deceive yourself: Plato did not use up all the good and easy moves, nor do you have to be a Plato to come up with original philosophy.
It is difficult to teach creativity, but here are three techniques that may help.