Boutique Law Firms, English Grammar and Usage, Small Law Firms

From Biglaw to Boutique: Grammar Police

Tom Wallerstein

I was shocked to discover that “[a]ccording to the Lawyer Statistical Report, only 14% of attorneys are employed in large law firms of more than 100 lawyers. The large majority of attorneys (63%) and law firm employees work in small offices of ten attorneys or less.”

I have no idea if those numbers are accurate. But the reason I was shocked is because the report should have said, “ten attorneys or fewer.” “Fewer” is proper when referring to countable items other than time, money or distance. “Less” is proper when referring to things that generally are not counted.

OK, maybe “shocked” is too strong a word, but I do cringe every time I’m in the grocery store confronting the grammatically incorrect express lane of “10 items or less” instead of the proper “ten items or fewer.” Conversely, I always enjoy reading ATL’s “Grammer Pole of the Weak” column that explores some technical grammar debate. I usually have an opinion no matter how arcane the question.

I can trace my own fascination with words to the first time I read George Orwell’s novel 1984 [affiliate link]. Before it became an Apple commercial, the book was a moving exploration of the vast power of language and the relationship between words and ideas. The hero of the novel was employed to edit books and newspapers and remove words that had been banned. The political and social role of “Newspeak,” the state-imposed language, was a central theme.

My fascination with words continued in college where I studied speech. With oration, at its best, your words could glow with the gold of sunshine. At its worst, your tongue is twisted with words half spoken. But I majored in philosophy, and especially the philosophy of language. Law, with its supposed emphasis on logic, language and speech, seemed a natural fit for me.

After all, as lawyers, words are our stock and trade. What is an argument but a collection of ideas, expressed in words, intended to persuade?

Contract disputes, patent litigation and many other legal issues revolve around disputes over the meaning of words. It is hardly surprising that lawyers should obsess over using words precisely, and bicker over grammar and punctuation. I welcomed that.

But then came the Blue Book, and I was appalled. Too many of the rules seemed arbitrary and cumbersome. I remember chuckling over a law review article by Judge Posner castigating the Blue Book, and over the years Judge Posner has kept up his scathing criticism, eloquently explaining what so many of us believed; namely, that the Blue Book was a scam!

At Penn Law, like many law schools, getting a spot on one of the prestigious journals required a tortuous, multi-day long Blue Book competition. Enduring the competition was, for me, worse than the first year curriculum itself. To many of us, the process was little more than formalized hazing. I understand that the process at Penn has improved since then, but I also know that Blue-Book hazing remains an unfortunate reality for many 1Ls.

Still, once I had finished the competition, and done well, I became an apologist for the Blue Book. I reasoned that attention to detail and mastering a set of arbitrary rules were both, after all, essential lawyerly traits. When I began my judicial clerkship, I found that my judge was just as meticulous as I in striving for perfect punctuation, grammar, and adherence to the Blue Book.

I remember well my first interview with my judge. He asked me what I was reading, and I showed him my copy of “The Footnote: A Curious History” [affiliate link] I think that was the moment he decided to hire me. I never did confess to Justice Verniero that I could not make it past the midway point of the dense book. Hopefully I showed more perseverance in the work I did for him.

After I entered private practice, I continued to pride myself on my mastery of the Blue Book and striving for linguistic perfection, however unobtainable. The lawyers I worked for encouraged my devotion. Even when I moved to California and switched firms, the partners encouraged us to strive for perfection in the written word. Because the stakes of our cases were so high, the time we spent making yet one more read-through always seemed justified. As our clients demanded, we left no stone unturned, nor any semicolon misplaced.

To some extent, my obsession with staying typo-free and striving for perfect grammar only increased when I left Biglaw. Now our adversaries were generally bigger and employed superior resources. We deemed it critical that our work product show them, and their clients, that we would provide the same quality of work as when we were in Biglaw. I’ve written before that “[w]hen litigating against big firms, it can be helpful to demonstrate early on that your team is capable of producing work product at or beyond the level of your opponent.”

Conventional wisdom also holds that better writing will win the respect of judges and therefore will, presumably, be more persuasive. That makes some sense, but surely there is a limit. Will prevailing on your motion for summary judgment really depend on whether you correctly choose a semicolon over a comma?

My father, who was born and raised in Cuba, never did quite master English. He lived in the United States for over forty years, but he always sounded like Ricky Ricardo and he never did quite get his prepositions right. He would promise to drop us “on” the mall, instead of dropping us off. He would say that he would return to pick us “in” instead of picking us up. He called me, “Tommy,” but with his accent it sounded like “Domey,” which is what my high school friends call me to this day.

My friends’ teasing of my dad’s accent was all in fun. But sometimes lawyers’ hypersensitivity to language reveals a deeper conflict between Biglaw and small. Like the ATL commentariat scouring one of Elie’s early posts, some Biglaw attorneys love to scoff at the typos they uncover in the work of their small law adversaries. They fancy that their own typo-free work is the natural product of their superior legal minds.

I’m sure that there are more sub-par small firm lawyers than there are sub-par Biglaw lawyers simply because more lawyers practice in small firms than large ones. But economics, rather than intelligence or training, also explains why small firm lawyers might tolerate more typos. Smaller firms tend to handle smaller matters. Every minute a lawyer spends doing anything has a potential benefit, and a cost. With a relatively smaller amount at stake, and a resulting smaller budget, it sometimes becomes bad business — or a bad investment for the client — for a lawyer to spend the extra necessary time to make his written work perfect.

Sadly, my dad died unexpectedly when I was in college so he didn’t live to see me go to law school. I’ll never know how he would view my fascination with words and language, or if he would feel I was striking the right balance between appropriate diligence and unhealthy obsession. All I can do is try to do the best I can, and remember the last words he said to me: “No matter what you do, I will always be proud at you.”

Tom Wallerstein lives in San Francisco and is a partner with Colt Wallerstein LLP, a Silicon Valley litigation boutique. The firm’s practice focuses on high tech trade secret, employment, and general complex-commercial litigation. He can be reached at

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