One of the best (and easiest) ways to become a more effective legal writer is to compose a brief as if you are having a face-to-face conversation with the reader. There are many ways to accomplish a conversational tone. Here are a few:
Avoid big words, if possible. Faulkner once said of Hemingway: “[Hemingway] has never been known to use a word that might send a reader to the dictionary.” Hemingway’s response: “Poor Faulkner. Does he really think big emotions come from big words?” This is not to say that you should dumb-down your vocabulary or your writing; it simply means that you should choose your words carefully, and use the most plain-spoken language possible.
Avoid legalese. Avoiding legalese is hard for attorneys because many seem to think that if they don’t use legalese they won’t “sound” like a lawyer. Nothing could be further from the truth. As Garner says, correctly, “unnecessarily complex legal jargon . . . doesn’t communicate efficiently, even to other lawyers, despite occasional claims to the contrary.” Modern American Usage pp. 489.
Use contractions sparingly. I’ve previously recommended using contractions sparingly to achieve a conversation tone. Think about it, do it, but don’t overdo it.
Keep sentences short, and to the point. This should be a no-brainer, but it’s common to read sentences in briefs that could be broken-up into more digestible parts. Nothing says “bad writing” more than a run-on sentence.
Practice these principles in other areas. These same principles can be applied in other contexts, such as oral argument. Former Solicitor General Paul Clement’s argument in the Obamacare case is a great example. Clement’s presentation was plain-spoken, to the point, and conversational, and thus was widely considered to be effective. You can hear his oral arguments on the Supreme Court’s website, especially Day 2, where the parties argued about the substantive constitutionality of the individual mandate.