I repeat: every lawyer should use outlining software.

Yet I can’t find anyone who does.

Back in the mid-90’s, I attended a Bryan Garner CLE on improving legal writing. Twenty years later, the three big takeaways I still remember are:

  1. outline before you write;
  2. shorter is better; and
  3. ditch the legalese (hereby, wherefore, hereto, etc.)

Here’s an article that says John Grisham spends more time on the outline than the book:

Ask John Grisham, and he’ll tell you he can’t write a novel without doing an outline first. He does a 50-page outline with a paragraph or two about each chapter, setting out the major events and plot points. He spends more time on the outline than on the writing. Robert Ludlum once told me the same thing — his outlines were often as long as 100 or 150 pages!

Sometimes I’ll write something without an outline because I think it will be so short I don’t need one. Usually, it’s a mistake. However great you think you do without outlines, you would be better with outlines.

I don’t outline blog posts because of time factors. If I did, the posts would be better organized and read better. Take this post for instance. The organization is not great.

For outlining, I’ve used the software NoteMap for years. It works well. I can’t practice without it (or something comparable). I use it for every deposition and witness outline and every brief.

I recommend using dedicated outlining software rather than outlining functions in Microsoft software like Word and OneNote. The key benefit of outlining software is that it makes it easier and faster to re-organize. With the click of a mouse, you can move questions or topics around, create new topics or sub-topics or delete topics or questions.

Drafting questions with outline software also makes it easier to recognize needed follow-up questions.

Organization of questions makes a huge difference in the clarity of witness outlines.

If I still worked at a big firm, I would train associates on outlining and force them to use outlining software for briefs and witness outlines. It would improve their work product and their analysis.