Trading Big Law challenges for entrepreneurial ones

This post first appeared in Hire an Esquire magazine.

A year or so ago, I wrote a post for Hire an Esquire about leaving Big Law after having my first child. I observed that the billable-hour model is unworkable for many parents, and I resolved to redesign the Big Law business model in my new role as a legal designer.

What I’ve come to realize, however, is that the challenges I spoke of are more widespread than Big Law, and have many different causes—not just the billable hour. Solo and small-firm attorneys often struggle financially because they were never taught the business side of running a practice in law school. And many attorneys at mid- and large-size firms want to start their own practice—not to escape the billable hour, but to have a sense of purpose and autonomy—yet they have no idea how to leave.

I’ve also discovered that the challenges I faced in Big Law did not all magically disappear when I went into business for myself. Even though it’s “only me” and I theoretically have complete control over my day, I still struggle to prioritize tasks, avoid digital distractions, and be present with my family. On top of that, I had my second child earlier this year, which has added more balls to the juggling act. As evidence, I submit this photo of me scheduling a meeting from my phone in the hospital after giving birth to my son this spring:

What I’ve come to realize is that designing a purpose-driven yet sustainable career requires a lot of self-awareness and self-assessment—whether you’re a solo or a Big Law associate. But most of us were never given the tools to develop that mindfulness and self-knowledge. On top of that, we were not taught how to manage knowledge work properly to deliver high-quality services to our clients while avoiding overwhelm and burnout.

After spending time expanding my own toolbox to include meditation and Kanban (a way of visualizing my workflow), I realized that other attorneys could benefit from these tools as well. That realization led me to join forces with my new cofounders to create Start Here HQ, which helps lawyers get unstuck, find joy, and create meaning through their work.

What’s amazing is that we formed this new collective in my house with a newborn in my arms. My co-founders gladly embraced the rhythm of life with a newborn and offered tons of assistance in terms of bouncing the baby and being at the ready with a burp cloth.

Creating a work life that aligns with my strengths and values without overshadowing my role as a parent has been an incredibly exciting and empowering journey. I hope that more of us will embrace these 21st-century ways of working and come to realize that we all deserve—and can have—a purposeful and joyful career.

Legal design in the news (for the wrong reasons)

Last month a federal judge fined a law firm $1,048.09 for filing a document with the wrong line spacing. The story made the legal-news circuit, but was not covered widely. I imagine that if people on the street were told about it, their reactions might range from What on earth? to Lawyers will be lawyers .... 

Stories like this disappoint me because everyone takes away the wrong message. In this case, the rule that the law firm broke is outdated and silly. And the law firm’s skirting of the rule was inappropriate and foolish. But what worries me most is that other lawyers who hear this story will be afraid to experiment with the formatting of their own briefs for fear of a similar rebuke. And if lawyers aren’t willing to push back on these silly formatting rules (in a principled way, unlike the firm in this story), then it will be even harder to improve the typography and readability of court documents, which I believe is crucial for our society.

Here’s what happened

Like several other judges in the Southern District of New York, Judge Marrero’s individual practices include a rule that certain types of briefs must be “limited to 25 pages .... double-spaced and in 12-point font with 1-inch margins.” (This is a terrible way to format documents, but that’s another post.)

In CaféX Communications, Inc. v. Amazon Web Services, Inc., the law firm representing Amazon, Susman Godfrey, filed a 25-page brief using 12-point font, one-inch margins and 24-point line spacing. 

What’s the difference between double spacing and 24-point spacing? Let me use Microsoft Word to illustrate. If you click the line-spacing dropdown menu, you get a list of choices: 1.0, 1.15, 2.0, etc. The term 1.0 is known as single spacing and 2.0 is known as double spacing.

If you click “Line Spacing Options...” you get even more choices. You could choose, for example, to set the line spacing to “exactly” 24 points, which is what Susman Godfrey did for its brief.

So, what’s the difference? Matthew Butterick explains on his website Typography for Lawyers:

Most courts adopted their line-spac­ing stan­dards in the type­writer era. That’s why court rules usu­ally call for dou­ble-spaced lines. On a type­writer, each line is the height of the font, thus dou­ble spac­ing means twice the font size. So if you’re required to use a 12-point font, dou­ble line spac­ing means 24 points.
Curi­ously, the so-called “dou­ble” line-spac­ing option in your word proces­sor doesn’t pro­duce true dou­ble line spac­ing. Microsoft Word’s “dou­ble” spac­ing, for instance, is about 15% looser, and it varies depend­ing on the font. To get accu­rate spac­ing, you should always set it your­self, exactly.

In other words, you might think that 24-point spacing would be considered double spacing when using a 12-point font, but because Microsoft chose to define “double spacing” as something more than twice the font’s point size, that is not true if you’re typing in Word.

Because 24-point spacing is tighter than “double spacing,” you can fit more lines of text on each page. By using 24-point spacing, Susman Godfrey was able to submit a brief that appeared to comply with the 25-page page limit, but was in fact “substantially longer.” (Although I was not able to obtain the original brief from the case, I ran my own experiment in Word and it looks like Susman Godfrey may have gained an extra 4.3 pages by doing this.)

According to Judge Marrero, Susman Godfrey deliberately flouted this rule in an attempt to gain some slight advantage in litigation. Because Susman Godfrey acted deliberately, the judge ordered it to submit a revised, compliant brief and to tell the court how much it cost to do so. Susman Godfrey said it cost $1,048.09 to resubmit the brief, and the judge decided to impose a fine in the same amount to deter similar conduct in the future. 

Here’s why this is all so silly

This story might cause you to scratch your head for a number of reasons:

  1. Imposing a page limit (as opposed to a word-count limit) is outdated. Word processors give us much more control over the formatting of our documents than typewriters did. Two documents with the same exact word count can take up a different number of pages depending on how they are formatted. Line spacing isn’t the only variable. If the court used a word-count limit instead, no one could “game the system” by tinkering with formatting.
  2. Even if Susman Godfrey’s trick had gone unnoticed, it’s unlikely that the extra four pages would have given it an advantage. Judges generally prefer shorter briefs that get to the point. Lawyers’ tendency to write right up to the page limit annoys a lot of judges.
  3. If an attorney really felt that she needed more than 25 pages to make her argument, Judge Marrero’s rules allow her to ask for an extension of the page limit. (Though, to be fair, he says that he will “entertain” such requests “only in rare cases where the facts and issues are particularly complex.”)

If this choice by Amazon’s attorneys really was a deliberate attempt to get around the page limit without having to ask for an extension (which most likely would have been denied), then it’s a prime example of why people can't stand lawyers. This is crummy behavior on a number of levels. 

On the other hand, I think there’s a possibility that the lawyers didn’t think they were “breaking” the rule. They may have thought that 24-point spacing of 12-point text would count as “double spacing” and thus technically comply with the judge’s rule. In their eyes they were simply picking their preferred interpretation of “double spacing.” (Or, possibly, they didn’t even think about this distinction at all and didn’t realize they were getting an extra four pages.)

Given the origin of the term double spacing, I don’t think this is a totally unreasonable argument. Moreover, other courts explicitly allow even greater variations. In California, for example, the court rules impose page limits on briefs but allow them to be either “one and one-half spaced or double-spaced.” Using 1.5 line spacing instead of double spacing allows for approximately 9.5 extra pages if you’re working with a 25-page page limit! 

Curiously, I have never seen a brief filed in California state court that was not double spaced (or at least 24-point spaced). Perhaps California lawyers are simply unaware that they have this choice, or perhaps they assume that all California judges have a strong preference for double spacing—as Judge Marrero apparently does!

I worry that this story will discourage lawyers from learning about typography and will cause them to interpret court formatting rules as conservatively as possible. Instead of using formatting tricks to flout the rules and gain a perceived advantage over one’s opponent, I wish more lawyers would learn how to use typography to improve the readability of their briefs. If more judges saw how typography could be used to make their jobs easier, perhaps we could persuade them to change the outdated court rules that perpetuate bad typography.

Look at all the amazing things AI can (and can’t yet) do for lawyers

This piece originally appeared on ReadWrite on April 12, 2017.

Robot lawyers have been getting so much attention lately that AI-and-law thought leaders believe we have reached peak hype. Journalists have responded by toning down their headlines to better manage expectations. For example, last month the New York Times ran an article titled, “A.I. Is Doing Legal Work. But It Won’t Replace Lawyers, Yet,” and the ABA Journal gently warned, “The robot lawyers are coming (to help, not to take your jobs).

The Times article explains that automation generally happens task by task. So, even if AI can scan documents and predict which ones will be relevant to a legal case, other tasks such as actually advising a client or appearing in court cannot currently be performed by computers.

But for readers who are not well-versed in the law, these articles fail to answer some more foundational questions: What is legal research, anyway? And, if a computer can do the research, why would I still need a human lawyer?

To answer those questions, let’s look at a specific technology as an example. The company Casetext recently unveiled a tool called CARA to help lawyers do legal research. CARA stands for Case Analysis Research Assistant (it also means friend in Irish). This rollout coincides with Casetext’s announcement that it has secured $12 million in Series B funding, which will be used in part to further develop their AI capabilities.

How does CARA work? The user uploads a legal brief to Casetext’s website; CARA scans the brief and instantly returns a list of relevant cases that the brief failed to cite. I tested it out with a brief I wrote a few years ago when I was still practicing law. CARA’s speed and accuracy are truly astounding. It would have taken me hours of research to come up with the list of cases that CARA generated instantaneously.

But for those who have not experienced the drudgery of legal research firsthand, it’s hard to understand what this all means. Readers may be wondering, What is a “relevant case” and why is it so important to make sure you didn’t miss one?

To appreciate the impact of tools like CARA, it’s important to have an understanding of how our legal system works. (Even if this was covered in a civics class at some point, most of us could use a refresher.) When a dispute ends up in court, the judge writes a decision resolving the case. Courts publish these decisions and they are collectively referred to as “case law.”

Our legal system is based on the principle of stare decisis, a Latin term meaning that cases should be decided consistently so that similar situations will yield similar results. Accordingly, when a dispute ends up in court, the lawyers and judge involved in the case look to older case law to see if the issue has been decided before. If it has, the older case will act as a precedent and the judge will follow its reasoning in deciding the current dispute.

Or, one of the lawyers may argue that the current situation is different enough from the older case to justify a different result. Even if there is a statute or regulation that seems to directly address the subject matter of a dispute, there may still be case law interpreting the language of the statute or regulation—filling in gaps or explaining how that rule applies to specific situation. In other words, no matter what type of dispute you have, it’s important to search all of the case law to see what judges have said about similar disputes in the past.

Enormous potential time savings

Before computers, cases were published in volumes organized chronologically. Lawyers would use the index to find cases relevant to their current dispute. This took time—lots of time. Even with the advent of computer databases such as Lexis Nexis and Westlaw, researching case law was still laborious because you had to try a lot of different word combinations to make sure you weren’t missing a case where a judge used slightly different terminology. Or your search term might be very common and you’d have to read through a lot of cases to find the ones that were most similar to your dispute.

CARA makes this process exponentially faster; she “reads” your brief so she understands the context of your dispute, and then she instantly searches a database of millions of cases and tells you which ones are relevant to your dispute—but she’ll omit the cases you cited in the brief, since you clearly know about those already.

As amazing as CARA is, however, the truth is that doing the case-law research is only part of the battle. If you’re involved in a court dispute, someone still needs to write the brief and show up in court to summarize the brief orally for the judge (among other tasks). There are companies out there, such as ROSS Intelligence, that are testing AI-assisted brief writing, but we’re still a ways off from robots showing up in court and talking to the judge.

In sum, lawyers perform a variety of complicated tasks. Computers can already do some of these tasks much better than humans—but not all of the tasks. Until that happens—or until we make lawyers’ jobs less complicated (perhaps an even more challenging task given the power of inertia)—we will still need human lawyers to wield these impressive AI-powered tools.