I’ve never been any good at figuring out when I’m done with a legal research project. This will come as absolutely no surprise to those who know my many personality flaws and obsessions.

For most questions, I can get the right answer in less than two hours, a definitive answer in less than two days, and a robust, scholarly understanding of the area of law in less than two weeks (but why stop there?). Figuring out which of those benchmarks is appropriate for a given task, however, or when I’ve reached it . . . well, that’s a little tougher. And things only get more complicated when I try to bring in an associate to help. Because, you know, control. OCD. Catholic guilt. And such.

With that in mind, here are some guidelines that I’ve developed over the years to rein in my worst impulses:

  1. What kind of appeal are we handling? Broadly speaking, there are two types of appeals: cases where you ask the court to correct an error, and cases where you ask the court to develop the law. To argue either case, you need to understand how the law works and why it works that way. But to argue a law-development case, it’s often helpful to have a broader and deeper understanding of the law. You’ll want to know, for example, how other jurisdictions have handled the issue, whether there’s a clear majority rule (and why), and if the law  is moving in a particular direction. The same information can be helpful in an error-correction case, of course, but it’s not always as necessary.
  2. Have we checked the obvious boxes? I tend to work my way through research problems methodically. I start with reliable secondary sources to get a broad understanding of the area of the law. (Big fan of context here.) Then I look at statutes and rules. Then I read the cases that showed up in my secondary sources and annotations. Then–and only when I understand what I’m looking for and how it fits into the area of law–I run some keyword searches and Shephardize my major cases for research. If I’m working with an associate–and I sometimes have to, because at my advanced age I’ve lost the luxury of spending days in the library–I’ll make sure that he or she has run through these steps. I would hate to learn that we found the answer to a civil procedure question in 20 minutes based on a word search without checking the rules or Wright and Miller. Don’t laugh. These things happen–even (and maybe especially?) at great big Am Law 200 firms.
  3. Am I bored yet? In most research projects, there’s a point where you see basically the same ideas showing up, with citations to the same authorites. When you reach this point, you’ll be able to rattle off those ideas, and you’ll have read the pertinent authorities, and you will know how they all fit into the broader legal landscape. This is where boredom sets in. I consider the boredom threshold the point where I know the answer to a legal question.* This may or may not be when I stop researching. Sometimes, I want to read every single case from a court on a certain point, so I can say things like “This Court has never held that . . . .” Other times–and especially in a law-development case–I will keep researching well past the boredom threshold because I want to see what other courts have done. If another court has gotten the wrong answer for a compelling reason, I’d like to know that before I submit my brief.
  4. Can I answer the tough questions? From an early point in the appellate process, I keep a list of “tough questions” that I should expect from the judges or justices. Sometimes these questions sound like “Have we ever ruled that . . . ” or “Do you have any authority for that proposition?” If I can’t answer these questions, then I’m not done yet.
  5. Can I explain it to Caroline? I have three kids: Caroline is 8, Jack is 5, and Cricket is 3. When I am comfortable with a case, I can explain it to Jack. When I am comfortable with an area of law, I can explain it to Caroline. And as any parent will tell you, there is no sense explaining anything to a three-year-old, so Cricket remains largely useless as a benchmark.

That, in a nutshell, is what I do. What do you think? Have I left anything big out?

*Unfortunate fact of legal practice #364: junior associates have no boredom threshold. This is why they are unable to meaningfully answer any legal research question and will instead hand you a 25-page, single-spaced memo that says “maybe.”