Jay Shepherd

Posts by Jay Shepherd

Have you ever messed something up for a client? Ever make a mistake that was yours and yours alone, that caused your client a problem and you and your firm some embarrassment?

If you haven’t, then you haven’t been practicing very long. Because you can’t practice for a long time without making some mistakes. It’s human nature, and anyone who tells you otherwise is lying or self-deluding.

In 17 years of practicing as a small-firm lawyer, I made my share of mistakes. More than some lawyers, perhaps; fewer than others. Not so many that it prevented me from getting a reputation among clients and peers as a decent lawyer. But more than I wanted to make.

Obviously, we should strive to minimize the number of mistakes we make as lawyers, and to minimize their severity. But one of the most important things to learn as a lawyer is how to handle it when you’ve made a mistake.

Here are eight tips to help you fix your mistakes and make your clients love you.…

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I hope you had a good Memorial Day weekend. I hope you were able to leave work behind for the long weekend and spend time with your friends and family. I hope you enjoyed good weather, maybe threw a ball around, grilled some steaks, and so forth. It was, after all, the Unofficial Beginning of Summer.

My long weekend was nothing like that. I spent it entirely inside, packing up the offices of Shepherd Law Group, preparing files for a storage facility, and boxing up the rest of the equipment and random stuff for my basement. For me it was, after all, the Unofficial Beginning of the Rest of My Life.

Let me explain: As you may have heard, I started a consulting firm called Prefix, LLC, to teach lawyers and other professionals how to price their knowledge. As a result, I made the decision to close my Boston employment-law firm after 13 years in business.

As I tape up my last box and peel away the sign from the office entrance, I thought I’d share with you some of the things I’ve learned running a small law firm. These are 13 things I wish I had known when I started.…

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It’s very difficult to get a job as an associate in a small law firm. First of all, there is a lot of competition. Many of you are between jobs. Many are at Biglaw jobs looking to get out. Many of you are finishing up law school and are still looking.

Don’t get me wrong: it’s also hard to get a job at a big firm. I know. But the path there is at least more straightforward: Go to a Top 30 (or so) school. Work hard. Finish in the top 20% or so in your class (the lower your school ranks, the higher grade ranking you need). Wear matching shoes to your on-campus interview at the start of your 2L year. Don’t get slizzard at your summer-associate firm functions. Pass the bar. Sell your soul. Collect your buck sixty.

Yes, yes, I know. It’s not that simple, and the large firms do look for other qualities, too. But no one in my class who met that top 20% threshold failed to get a Biglaw summer-associate job.

The path to small-firmdom is more circuitous. And by “circuitous,” I mean “there is no path.” It’s certainly not about being smart, working hard, and getting good grades and a good education. Those are table stakes.

But I’ve identified the ten traits that make the best candidates for a small-firm-associate gig. See what they are after the jump.…

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I’m a huge Red Sox fan. (That noise you just heard were all the Yankees fans skipping ahead to the comment section. Don’t wait, guys. I’ll be right there.) This season began with the highest expectations, after the Sox won the offseason by acquiring superstars Adrian Gonzalez and Carl Crawford and by rebuilding their bullpen. Experts and fans alike were predicting a 100-win season (their first since 1946) and a nonstop flight to the World Series. Instead, the team got off to a horrific start, going 0–6 and 2–10. Since then, they’ve begun to turn it around, finally reaching .500 on May 15. Now they’re just half a game out of first place in the tight AL East.

Part of the reason for this turnaround has been excellent pitching. Jon Lester, the young lefthanded cancer survivor, sits atop the American League leaderboard with a 6–1 record; no AL pitcher has more wins. Josh Beckett, the veteran star rebounding off a couple down years, is 3–1.

Now just looking at wins, you’d think that Lester is outperforming Beckett. But you’d be wrong, because win totals tell you very little about how a pitcher is performing. Just as looking at hours-billed totals tell you very little about how a small-firm lawyer is performing.

Better ways to measure performance (for pitchers and lawyers), after the jump.…

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Every so often a lawyer with a small firm will ask me what to do about providing employees with paid sick days. The practice is much more common in large firms, but many lawyers have come to expect it as a perk no matter how big their firms are. (To be clear, I’m talking about paid-time-off policies, not legally required unpaid leave like the Family and Medical Leave Act.) Many larger firms allow their employees to accumulate and bank their leave, saving it up for a rainy day, as it were. Some have the days expire after a certain time, while others allow the days to survive until the end of an employee’s tenure.

That’s fine at large, wealthy firms, who can well afford to pay people not to work. But what about small firms, where a person’s absence is more likely to have an impact? How many days of paid sick leave should a small law firm’s policy permit?

My answer might surprise you. Not ten days a year. Not five. Not even three.

Zero. Small law firms shouldn’t have a policy of any days of paid sick leave a year.

But before you set your comment phasers to “kill,” give me a chance to explain.…

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Have you ever noticed that some lawyers become different people when they get in front of a keyboard?

It’s like a Jekyll-and-Hyde kind of thing. They might be perfectly pleasant individuals in real life, capable of warmth or at least civility to their fellow human beings. But get them in front of a computer with a law-firm template on the screen, and they turn into some sort of lawyerly unmanned drone.

Most lawyers, especially junior lawyers, have an idea about what a lawyer letter is supposed to look like. It generally has fancy lawyerly words like “pursuant to,” and it usually includes lawyerly weirdnesses like parenthetically writing numbers in figures after having just spelled out the numbers in words (“If we do not receive a response for you and/or your counsel in five (5) days …”), and it almost always contains threats about Very Bad Things happening. And they tend to be uniformly douchey.

But here are four (4) reasons why lawyer letters are less effective than phone calls.…

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You always hear this business axiom: “The customer is always right.” Whether true or not, you’re supposed to at least let the customer believe that he or she is correct. But in my experience, that doesn’t always work.

Before I went to law school, I was a banker. (That sentence makes me sound old, since I started law school 20 years ago this fall. Whatever.) Anywho, in my years as a banker, I frequently had to explain to customers the vagaries of the American banking system. “What do you mean my money’s not in my account? I just deposited the check. Of course it’s there!” No, sir, I’d have to say. Your money’s not there. Your check hasn’t cleared. The customer was very often just not right.

Turns out, practicing law isn’t much different. Your clients are often wrong. And your job as their lawyer is often to tell them that they’re wrong.

Even if it gets you fired.…

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Did you watch Lost? I was a big fan of the show, which ran on ABC from 2004 to 2010. The series required quite a commitment from its viewers, since it had a large ensemble cast and was a true serial — you really couldn’t miss any episodes. After the third season, the producers made the unusual announcement that the series would definitely conclude at the end of the sixth season. Since so many elements of the show remained a mystery until the very end, it became a guessing game as to whether the writers would be able to tie everything together into a satisfying ending.

Toward the end of the final season, the show revealed a location that we’d never seen before that was crucial to explaining the Island’s secrets. (I’m not giving anything away here if you haven’t seen it.) But the location, a glowing cave, was rendered with cheesy special effects that looked like they’d been borrowed from the original 1960s “Star Trek” series. The bad effects were so jarring that they took the viewer out of the story, causing you to say, “What’s with the cheeseball special effects?”

What the heck does this have to do with improving your legal writing? Find out after the jump.…

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There comes a time in the career of every law-firm lawyer when she realizes that her bosses are acting like idiots, that “they’re doing it wrong,” and that she could do a better job if she were running her own law firm. Most of the time, that idea goes no further: the lawyer rattles off a few choice curse words, ignores the partners’ shortcomings, gets the work done the way they want it, and lives to fight another day.

But for a small minority, this outburst becomes an epiphany, and then turns into a dream (kind of like Inception, but in reverse), then an obsession, then finally a reality. Others, like me, always knew that they they were going to start their own law firms, and it didn’t take frustration with partners for that idea to form.

So when’s the perfect time to start your own firm? The answer is the same as for the question of when’s the perfect time to start having kids:

Never.

But forget the “perfect” time. When’s the best time to start your own firm?

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I have a temper.

That might surprise people who know me casually, like my professional acquaintances. I work hard to keep it in check. Over the past 17 years as an employment litigator (representing companies), I’ve gotten better at controlling my anger. But it hasn’t always been easy.

Because lawyers can be pretty adept at pissing people off.

In fact, I know many people who left litigation — even left practicing law altogether — primarily because they were sick of dealing with obnoxious opposing lawyers. And I’m not talking about thin-skinned, confrontation-avoiding types. I’m talking about solid, talented litigators who just stopped finding it fun to fight with douchebags all the time.

And this is more of an issue for newer small-firm lawyers, who are much more likely to deal with opposing counsel early in their careers than their Biglaw counterparts. (Maybe someone else here can write a post on dealing with obnoxious document reviews.)

So to help you deal with the toolbags that all litigators face from time to time, here are five tips that I’ve picked up along the way….

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