Biglaw, Boutique Law Firms, Job Searches, Secretaries / Administrative Assistants, Small Law Firms

From Biglaw to Boutique: Bad Hires

Tom Wallerstein

It was our new receptionist’s first day at our office. I was in our kitchen, and I found a potato wrapped in a paper towel. Because it was a raw potato far in the back of one of our unused kitchen drawers, I had no idea how long it had been there. Months, maybe. So I asked Cassidy, the new employee, “Is this your potato?”

Cassidy was slouched nearly horizontal in her chair. She looked at me with an expression of vague annoyance, and reached up to remove her iPod earbuds. She mumbled a response but didn’t really answer me. So I asked again, “Cassidy, I was just curious, is this your potato?”


I repeated my question for the third time and finally she replied, “I don’t know. Maybe.”

I tried a different approach. “Let me put it this way. Have you brought a potato into the office in the six hours you have been working here?”

“Um… Yes.”

Progress! “Well, then I think it’s safe to say that this is your potato. Mystery solved.”

The earbuds went back in and we let Cassidy go the next day. She called our office about a week later, asking to retrieve a pair of scissors and… you guessed it, her potato….

A firm is only as good as its people, and hiring the right people is both important and difficult. A bad hire drains a small firm financially and emotionally, and impedes its growth.

My firm’s very first employee was, in retrospect, a bad hire. After founding our firm, my partner and I quickly realized we would benefit by paying for administrative help, and we resolved to hire someone. But we got greedy. Given the opportunity, why not take advantage of the luxury of hiring an admin who also had a J.D.? By doing so, we figured that we could have an attorney who could perform billable work but also fill our need for admin help.

We placed an ad and were delighted to get a response from Charlie. Charlie was a Yale Law grad who had an appellate clerkship before working for a mid-size firm that was well known to me. I could not believe our good fortune in receiving such a stellar résumé and looked forward to our interview. When I interviewed Charlie, I was blown away. He was eloquent and charismatic. His personal story was compelling. It was impossible not to like him.

I called his reference — someone I already knew — and left a message. Charlie assured me that he would receive a glowing review. The reference never called me back, and I assumed she was just too busy with the press of work. We hired Charlie.

Charlie didn’t work out because he was vastly overqualified for the menial administrative tasks we most needed done at the time. We learned a valuable lesson that being overqualified is potentially as problematic as being underqualified. We needed an admin and we should have hired an admin, not a Yale Law grad.

Our false start with Charlie also taught me the lesson not to rely too much on charisma and personality. Having the appropriate technical skills for the task at hand is critically important, no matter how much you might personally like the candidate. (On the other hand, of course, having all the requisite background and experience won’t matter if the employee is not a good “fit,” especially in a small firm.)

I also realized, in retrospect, that there might have been a reason Charlie’s reference never called me back. That was a red flag that I ignored in my excitement to hire someone who appeared to be such a superstar, at least on paper. References are critical when hiring and should never be ignored.

Ignoring red flags that arise during the interview process is almost always a mistake. You have to trust your gut, and if you get an uneasy feeling during the interview, you can pretty much bet that the candidate is not going to work out.

Fast forward two years. Our firm had continued to grow, adding attorneys and other staff, and we were now hiring another admin. We interviewed Bobby, a candidate who was good on paper and presented well. We were ready to extend an offer, and all that remained was the reference check.

I try not to make the same mistake twice, so this time I made sure I had feedback from the reference. She told me that she would definitely not hire Bobby again, especially since he had been suspected of selling OxyContin as a side job. Another tragedy narrowly averted.

One way to minimize the likelihood or effects of a bad hire is to avoid hiring out of desperation. All of my false starts were the result of us being in dire need of help. Our desperation led us to make rash decisions that we might have avoided had we felt less pressure to fill the role. If you have an immediate, urgent need for help, then the better course is to hire a temporary worker. That resolves your immediate need and buys you time to find the perfect long-term candidate.

Try to settle on two or three candidates, any one of whom seems acceptable in terms of objective qualifications, personality and fit, etc. If your interview process results in one and only one acceptable candidate, then you are going to feel undue pressure to hire that person. Especially when the need is urgent, you may become so relieved to know that there is help on the way that you overlook red flags or settle for a less-than-ideal candidate. So keep looking until you have several candidates from which to choose.

Some false starts are probably inevitable when hiring, even in a bad economy with an abundance of candidates. As I’ve written before, “the smaller the firm, the greater the relative importance of each associate.” A Biglaw firm will not be crippled by hiring a single ineffective secretary or associate. A firm of three or four attorneys, however, could be. For this reason, minimizing false starts and avoiding bad hires is critically important to small firms.

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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