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I was a COA clerk and do a mix of complex litigation and appellate so I run into this issue with court imposed page limits often. Brevity is probably the hardest part of legal writing and even the best practitioners struggle with it. I start off by writing the brief exactly as I would if there was no page limit, run all of the arguments to ground. Then I go through and tighten up the language. This is free argument space you can gain by using pithier words. I then read through it, see if there’s anything I can cut substantively, as well as anything that would be better addressed as a footnote. At this point, I circulate it to another lawyer to review as you’re probably too close to it by this point and think all of your arguments are necessary. Another attorney will be able to cut though that.
I was also a COA clerk. +1 to this.
My judge would often send drafts back to me with a comment of "this is great analysis but it's too long" and ask me to cut 40% of the length. This felt brutal but proved to be valuable training.
Also a court of appeals clerk. I learned to consider the most direct way from point A to Z. On the appeals level, it’s important not to make unnecessary law. Similarly, while you may need to brief many issues to preserve them for appeal, you will want to invest most of your words in arguments that are dispositive of the case.
F
I always remember that no one reads that sh*t
I clerked at the district and appellate level. I assure you, judges and their clerks, unfortunately, read that shit.
I do an initial round of legal research to get lay of the land on the issue, then outline the brief prior to writing anything, then begin writing and put it all on paper.
I then go back, perhaps after some further legal research, and for pretty much every sentence/paragraph, I ask “does this merit inclusion? What am I trying to convey, argue, or otherwise support with this sentence/paragraph?”
Often, I realize I can effectively address the issue in a matter of a sentence or two, even where I may have previously drafted several paragraphs/pages.
…similar to this response, where I’ve rambled on and could have simply said “every word should earn its place.”
write. read. revise. repeat.