Don’t Hate. Annotate.

June 6, 2024


“When we mean to build, We first survey the plot, then draw the model.”

          • William Shakespeare, Henry IV act 1, sc. 3

            Once you have identified the pertinent facts, applicable law, and best legal issues, you are ready to develop an annotated outline of your brief. This can be the most challenging part of writing. It is well worth the struggle. Writing from an outline is a reliable tonic for writer’s block.

            Understanding this concept was a big breakthrough for me as a legal writer. I found myself in agony working on a number of briefs and other writing projects at the same time. The idea of breaking down the writing process into logical steps seemed like the antithesis of creativity. It turned out to be just the opposite. Building an annotated outline allowed me to focus on one part of the process at a time, while skipping around to different parts of the process in other cases in an organized way.

            Painters often use a grid to organize their work on a large painting. An appellate lawyer must have their own grid to organize the art of their brief. The annotated outline serves as just such a grid.

            Try this approach:

    1. Organize your research under topics;
    2. Note holes in the rules of law and continue to research;
    3. Draft small portions of your brief based on the rules of law you are sure to apply;
    4. Continue to research, revising your plan based upon your findings;
    5. Finish and update your research;
    6. Outline your argument. Generally, the structure of the controlling rule of law will determine the outline structure. A multi-factor balancing test will be structured differently from a test that has a threshold issue. Deal with threshold issues first. For example, when appealing summary judgment in a negligence case on the ground that a material issue of fact existed on breach of duty and causation, your argument will have two parts, each related to the material issue of fact you must establish on both elements of your case. Let the structure of the rule control the structure of your argument, wherever appropriate;
    7. As you find your analytical flow, add your cases to the outline. Match cases to the points you want to make. Choose the best cases, winnowing them down as you go.

            Completing an annotated outline of your brief requires commitment to process. But you will have a lousy product if you cut corners here. Like the prep work that occurs before painting a mural, a detailed outline enables you to start writing from any point. You can only write one section at a time anyway. Annotating an outline facilitates a smoother transition from research to writing.