Jay Shepherd

Posts by Jay Shepherd

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

Seriously. Why? I don’t mean in a “because I couldn’t get a BigLaw job” way. I mean, “Why are you practicing law in a small firm?” And if you’re looking for work in a small firm, why? In fact, I really want to know why you’re a lawyer in the first place.

More importantly, your clients want to know. They might not realize it, and they probably will never ask you, but deep down, they want to know why. Why do they want to know? Because why you do what you do is what attracts clients; it’s what makes them want to work with you.

I can already hear you scoffing: “My clients work with me because I’m a good lawyer, or because they like me, or because they have a history with my firm, or because I’m so freakin’ good-looking.” Maybe so. Maybe that’s why they started working with you. But that’s not why they’ll stay with you. They’ll stay with you because of why you do what you do. So you need to figure out your why.

But how do you find your why? This guy can help you….

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Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

As the owner of a small law firm, I’m always surprised at how many blind résumés I receive in the mail. First of all, who even uses mail anymore? Does anyone seriously think that I’m going take them more seriously because they used cream-colored, 100% cloth, 24-pound bond paper? I’m not.

But forget the résumés for a minute; for me, it’s the cover letter that tells me whether I want to interview this person. Over the years, I’ve received thousands of cover letters from lawyers and law students. I’ve gotten to the point where I really don’t need to read the résumé before I’ve made my decision.

So with that in mind, here are 11 tips for writing cover letters to potential employers.

1. Spell my frikkin’ name right. You’d be astounded at how many times candidates blow this one.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: Enclosed Please Find … No Reason to Hire Me”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

There’s this great little Chilean sandwich shop near my office in Boston. Now I don’t know the first thing about Chilean cuisine, but it says “Chilean” on the sign, so that’s good enough for me. They serve sandwiches on these freshly baked flat loaves about the size of a pita but maybe five times as thick. They put chicken or steak on the bread, then steamed green beans — apparently that’s the authentic Chilean touch — plus Muenster, tomatoes, avocado spread, a creamy hot sauce (that’s very hot), and salt and pepper.

The shop, called “Chacarero” (which apparently means “chacarero”) started with a pushcart, then a lunch counter (in the old Filene’s building, which is now just an empty hole in the ground), then two full-blown restaurants.

But apparently things aren’t going well anymore, because they abruptly closed one of the two restaurants, and the other one seems less busy. And if you ask me, it’s because they’re making a mistake that many small law firms make.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: Green Beans and Credit Cards”


Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

Most small law firms are staying away from social media when it comes to marketing, according to a new report from Chicago-based Total Attorneys. The report, which you can see here (a short 6-page PDF), had a section about which marketing methods solos and small firms found most effective. The leading methods were:

  • online directories (17.7%);
  • word of mouth — which isn’t really a method, but more of a thing that happens (15.5%);
  • group-advertising ventures (whatever the hell that is) (13.3%); and
  • Yellow Pages (8.9%).

The takeaway for me from that list is that small-firm lawyers don’t know what they’re doing when it comes to marketing. “Word of mouth” means sit back and hope someone tells someone else to hire me, “group-advertising ventures” sounds like some sort of mail-order scam, and I didn’t know they still printed Yellow Pages. When my daughter asked me what Yellow Pages were, I told her that they were what little kids used to sit on to reach the table. (Sorry, Yellow Pages advertisers. Oh, wait. You’re not reading this because you’re offline.)

But the more-interesting fact to come out of this report is that two-thirds of respondents don’t do social-media marketing at all.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: 7 Reasons to Avoid Social Media”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

Let me tell you about a couple of cases I lost. Now, wait: before the Commentariat sharpens its knives (“This guy couldn’t get a big-firm job, then loses all his cases. No wonder he’s writing for ATL. Heh.” — Guest), let me point out a few things. In 17 years as an employment litigator, I’ve won plenty more cases than I’ve lost. But I didn’t learn as much from the cases I won; I learned much more from the ones I lost.

So this post covers the single most important lesson I’ve learned in litigation, and now I’m sharing it with you. You didn’t learn it in law school, and you’re not likely to find a CLE on it. But the lesson these two cases illustrate can prevent you from making the most common mistake lawyers make.

And learning that lesson will help you win more cases.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: It’s Not About the Law”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

Let’s get one thing straight here. It’s a universal law: You can’t give yourself a nickname. Only someone else can give you a nickname, and it has to happen pretty much organically. There’s nothing more pathetic than someone trying to force their own nickname on you.

I once had a prospective client whose name was “Tony Calabrese” (only it wasn’t; this is another pseudonym), but who told me to call him “T.C.” In fact he told me several times, mainly because I ignored him. Did he think I was going to have trouble saying his name? Neither his first name nor his last name was difficult to pronounce. You know the saying “the client is always right”? Well, you can forget about it when the client tells you to use a silly nickname. I didn’t take the case, because I couldn’t take him seriously.

The T.C. wannabe obviously liked the idea of being a nickname kind of guy. He thought it made him seem cool and hip. Like “Top Cat.” But this T.C. was no Top Cat. He was a software salesman. In contrast, Top Cat was the indisputable leader of the gang. The boss. The pip. The championship. (What the hell does that even mean?) But even in Top Cat’s case, only his “intellectual close friends get to call him T.C., providing it’s with dignity.”

So bequeathing yourself a nickname makes it look like you’re trying too hard. And yet small-firm lawyers do it all the time.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: T-Bone, Esq.”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

About ten years ago, my former law partner and I were involved in a noncompete case against the fourteenth-largest firm in the country. (It’s since slipped about forty spots. As you’ll see, payback’s a bitch.) The ginormous firm hit us with an emergency motion for injunctive relief, and gave us only two days before the hearing to respond. At the time, there were just two of us in our firm, and we were busy with a couple other matters as well. So we called up the lawyer on the other side, explained our situation, and asked him to indulge us with a short extension.

He replied, “No, I’m a douche. You can’t have an extension. See you in court.” It’s possible that I’m misremembering some of the actual words, but my recollection of the meaning is spot on. So my partner and I cleared the decks of our other work, buckled down, pulled an all-nighter, and got our opposition brief done in time for the hearing. Oh, and won.

The following week, the tables turned. We filed a motion to get the case dismissed for forum non conveniens, marking the one time in my career that I actually used something I learned in law school. We filed and served our brief and got a hearing scheduled for four days later. Then our opposing counsel called and — wait for it — asked us for an extension.

What do you think my partner told him?

double red triangle arrows Continue reading “Small Firms, Big Lawyers: Don’t Be an Extension Douche”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

It’s been many years, but I still remember the steps I took to land a job at a small law firm. Even though some of the methods have changed with technology, law students and potentially on-the-move associates might find this tale instructive.

After flaming out in the on-campus-interviewing process, I went to the library and looked up law firms in the Boston area. (This was before the Internet but after libraries.) I wrote down the names of dozens of firms, then went to the Martindale-Hubbell books and looked up the different firms. (Yeah, I know: quaint.) I selected lawyers whose practice areas or backgrounds or law schools or something seemed like a match for me, and I wrote down (in actual handwriting) their names and contact information. I then went back to my apartment, fired up the Wang word processor (OK, now I’m just messing with you), and entered them into a mail-merge form letter.

I then mailed dozens of nearly identical form letters (“Dear Lawyer …”) to attorneys around Boston, enclosing completely identical copies of my résumé. The letters said basically the same thing as the résumés, except in paragraph form (I used bullet points in the résumé), and asked for an interview.

Guess how well this method worked.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: The Secret to Finding a Small-Firm Job”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

Many Above the Law readers are currently facing dismal job prospects as the law-firm economy continues to trail the national economy. Some are law students contemplating graduation without an offer in hand. Others are junior associates who fear the return of mass layoffs. Still others are recent graduates bouncing between contracting jobs and other stopgaps. And the solution that many of these readers are arriving at is to start their own firms. As someone who did that 13 years ago, I applaud the sentiment. But before you go shopping for shingles to hang, I have one — and only one — question for you:

Do you want to run a business, or do you want to practice law?

I’m not being facetious here; it’s a completely serious question. But I’m afraid it’s not a question that most budding shingle-hangers ask themselves. And the answer is crucial: your future happiness depends on it. Because unfortunately, many lawyers start their own shops for exactly the wrong reason, and they find themselves in the worst possible job they could imagine: working as an underpaid wage slave for a complete idiot of a boss. (Themselves.)

I give a lot of informational interviews to newer attorneys or to law students who (think they) are interested in starting their own practices. And I always ask them this question, and most of the time, they answer: “Both.”

And I think: Danger, Will Robinson. Because “Both” is the wrong answer.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: The Key Question for Shingle-Hangers”

Ed. note: This is the latest installment of Small Firms, Big Lawyers, one of Above the Law’s new columns for small-firm lawyers.

Nor does it create an attorney-client relationship between you and Above the Law. It may also constitute attorney advertising, depending on the state you’re in (such as boredom or apathy). Please consult the laws of your jurisdiction. If you have received this post in error, please print it and mail it to Elie. Then delete it (the post, not Elie) from your computer.

That’s right kids: I’m writing about email footers. Squee! I noticed that when Mark Herrmann wrote about email subject lines, he whipped the Commenting Class into a frenzy. Well, get out the chum buckets, Captain Quint.

Nothing says “lawyers” like a good generic email footer. They first appeared around the turn of the century, soon after law firms begrudgingly accepted that “The Email” was here to stay. (Though I’ve heard that some firms still use fax machines. Perhaps only because their telex machines are busted.)

Like most things lawyers create, standard email footers were born out of fear. Such as fear that a single email exchange would lead some moron to think that he’d entered into an attorney-client relationship. Or fear that the authorities would consider an email about lunch plans to be improper attorney advertising. Or fear that an email containing a drunk-kitty YouTube video would somehow destroy someone’s attorney-client privilege.

As if.…

double red triangle arrows Continue reading “Small Firms, Big Lawyers: Disclaimer — This Post Contains No Tax Advice”

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