Associate Advice, Job Searches, Small Law Firms

Small Firms, Big Lawyers: Thinking of Quitting? Read This First

I tried to be a good boss over the years I ran my law firm. Some of my lawyers might tell you that I succeeded; others might be less charitable in describing my managerial skills. But I always made an effort to have my employees feel valued and respected. I gave them autonomy in their work, and I let them push back if they disagreed with the course of action I had chosen. When there was a problem with someone’s work or attitude, I dealt with it discreetly and sensitively; I never called anyone out in front of a coworker. And when someone had a good day, I made a big deal of it and made sure that everyone else knew about it.

I made sure that we celebrated every employee’s birthday, and we always recognized big events in people’s personal lives. And for a while, I gave a shout out to people for celebrating an anniversary with the firm.

Until one day, when I suggested going out to lunch to celebrate a junior associate’s second anniversary.

And she started crying.…

These weren’t happy tears over the prospect of a free meal. (Which wasn’t unheard of; we were big on lunch.) Instead, she felt bad about celebrating her anniversary at the firm.

Since she was quitting.

Needless to say, we didn’t end up doing the anniversary lunch. Instead, she explained that after a couple of years, it was time for her to move on. To be sure, I wasn’t paying her a heck of a lot (this was very early in the firm’s history) and she was ambitious. So once I got over my emotional reaction, I could understand her reasons for leaving. And to her credit, while she was excited about her new gig, she felt sad about leaving.

When a small employer loses a member of the team, it’s a big deal. Assuming the boss actually liked and valued the employee (I did), he or she is apt to feel hurt, surprised, spurned, and even betrayed. In many ways, it’s the surprise that really gets you, because you were planning a future that included that person, while he or she was planning something altogether different.


But the problem is, there really has to be some surprise involved. The prudent thing to do before quitting your job is to have another job already lined up. You’re stupid not to. And you really can’t walk into your boss’s office and say, “Hey, boss. Don’t take this the wrong way, but I’m sick of working at this dump and am going to start interviewing at other places.” As a former legal employer, I can tell you that that method rarely works. The natural response would be for the boss to say, “I quite understand. Let me help you by giving you even more time to pursue your job search. We’ll mail you your stuff.”

What is more, since most businesses only operate during, you know, business hours, it’s difficult to interview during the day when your current law firm is also operating. So you end up with basically two choices: (1) Try to schedule all your interviews outside of work hours (before or after your normal shift, or at lunch), or (2) lie. The problem with (1) is that prospective employers might not be as accommodating as you’d like, especially if they don’t really know you yet. And as you get deeper into the process, you may have a series of callbacks where you meet with several people in a row. This makes it almost impossible to schedule during lunch or early-morning hours.

So that leaves you with Door Number Two: the lying option. In retrospect, I learned that my lawyers who had left had placed various appointments on the calendar that were, quite frankly, fake. Doctors’ appointments are the most common, because an employer probably won’t ask you about it (and shouldn’t). Dental visits and hair appointments are also popular. (“Hmmm… her hair doesn’t really look that different. But her teeth sure are sparkly.”) Random visits with out-of-town family members was another category.

I’m not going to advocate that you lie to your employer, because of the lying part. But people do it, and I did it, too. (I think it was on a “dentist’s appointment” that I signed my first lease for my nascent law firm while I still worked at my old one.) The danger of the dishonest method — aside from the moral issues — is that there’s a serious risk of getting caught. You do not want your boss or colleagues to see you coming out of a law firm’s building when you were supposed to be in the chair at Hair Apparent. (Sidenote: Why do hair salons insist on having puns for names? There’s even a Flickr group devoted to this phenomenon. I think “Shear-n-dipity” is pushing it. And what if law firms did this? Discuss.)

From my own experience as an employer, I can tell you that sometimes these devices worked, and sometimes they didn’t. I knew that some of my employees were job hunting, although I never said anything. Others took me by surprise. Not sure which was worse.

The important thing to remember is that you’re probably going to need to deal with your soon-to-be-former employer again in the future. If you stay in the same town, you’re likely to bump into them at bar functions, in court, or even on cases. After the transition to your new place, you might need to call up and ask about a case or a document that you worked on. Whatever the situation, you’ll be much better off if you go out of your way not to burn your bridges. Shooting your way out of Dodge might feel briefly satisfying, but it will come back and haunt you down the road.

Instead, sit your boss down (probably best at the end of the day), and break the news gently. Say positive things (if you can think of any) about your experiences there, and then say that it’s time for you to try something new. If you’re leaving because you’re unhappy, the less said about that the better. You’re not looking to get into a debate about the merits of working there; you’re simply announcing your departure. Feel free to go with a variant of the “it’s not you; it’s me” speech. (You’ve given that before, right? Or received it?)

Offer to stay on a reasonable amount of time to help with the transition, but don’t be surprised if they don’t want you to stay that long (or at all). Above all, try to leave your boss in a place where he or she will feel good about you after the initial surprise has faded.

Lawyers no longer stay at firms forever; that’s a fact of life now. But people can hold grudges forever, and you really don’t want to start one. People will remember how you leave a place almost as much as they’ll remember how you worked there.

So quit carefully.

Jay runs Prefix, LLC, a firm that helps lawyers learn how to value and price legal services. Jay Shepherd also spent 13 years running the Boston management-side employment-law boutique Shepherd Law Group. He writes the ABA Blawg 100 honoree The Client Revolution, which focuses on reinventing the business of law, and Gruntled Employees, a workplace blog. Follow Jay on Twitter at @jayshep, or email him at

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