I’ve been experimenting with using ChatGPT to prep for oral argument. I always do the thinking myself first, putting together my silly lists, outlines, and tough questions. But then I’ve been using AI to backstop or refine my work. It’s pretty good!

Here’s the basic process: First, I tell the client what I’m planning to do and why, and I get their consent. Second, I create a project and upload the briefs, the key cases, and maybe parts of the record. Third, I write a pretty detailed prompt explaining what I’m trying to accomplish (e..g,, “I am counsel for the appellant, and I am preparing for oral argument …”). Generally, and this is just me, I like appellate output in the voice of Elena Kagan, John Roberts, our Paul Clement–both because they’re good, and they seem to have a sufficient corpus of work for the AI to play with. I haven’t tried Elizabeth Prelogar yet.

Then I ask it questions along the following lines (these are not the actual prompts, but the general topics; no sense spelling out the actual prompts, because the AI would love to help you optimize them):

  • Pretend that you are a judge on the Court of Appeals of Virginia. What would bother you about this case?
  • Pretend that you are a judge on the Court of Appeals of Virginia. After reading the briefs, what would want to learn about this case at oral argument?
  • What are the 150 record citations that appellant’s counsel needs to master to be ready for a 15-minute oral argument? Please give me a summary organized by topic, listing the record page number and a summary of the material included there.
  • Please prepare a table summarizing the respective positions of the appellant and the appellee on the key factual and legal issues in this case.
  • What are the three most important arguments in the brief of appellee (and any amicus) that are not addressed in the reply brief?
  • Please summarize the attached opinion in 5 paragraphs. (I’ll sometime ask it to focus on a specific issue, highlight a dissent, present the output in a certain format, etc.)
  • Please rank the three strongest arguments for each side.
  • Please prepare a list of 25 key questions the appellant should be prepared to address at oral argument.
  • Please outline the oral argument you would give if you were the appellee. (Remember, I’ve got the appellant.)
  • Please run a moot court for the appellant. Please imagine a hot bench that is focused on issue x. Please remember that judges ask follow up questions and interrupt counsel. Please present the moot court in the form of a dialogue.
  • If the appellant is asked x at oral argument, I believe that the answer is y. Can you help me optimize this answer for oral argument?
  • Pretend that you are a judge on the Court of Appeals of Virginia. Please review these materials and do any additional research necessary, then write a 2,500-word opinion deciding the case.