Biglaw, Boutique Law Firms, Small Law Firms

From Biglaw to Boutique: Never Satisfied

Tom Wallerstein

My six-year-old is never satisfied. If I offer him a piece of candy, he asks if he can have two pieces. If I tell him he can watch a 30-minute TV show, he asks if he can watch a 90-minute movie.

As annoying as that can be, I have a grudging respect for his persistence. In my opinion, his attitude exemplifies the kind of approach I think makes for a successful lawyer, not to mention running a successful business.

Refusing to be satisfied pays dividends in terms of your professional development. At the same time, the instincts of a six-year-old may be counterproductive. For example, when a case resolves unfavorably, our knee-jerk reaction is to blame forces beyond our control. You lost because the jury got it wrong, or the judge didn’t understand something, or the client didn’t tell you something. The words come out like an angry stream. There are a dozen rationalizations for why it was anyone’s fault but your own. Hopefully, when the heat cools down, and you find your mind, you will ask yourself what you could have done differently.

But I think what is less common, yet equally valuable, is going through this exercise even when a case resolves favorably. There is always room for improvement, and a post-mortem debriefing always makes sense. Rather than being satisfied with reaching a great settlement, or a great victory at trial, it behooves you to consider not only what you did right, but what you might have done differently….

The same concept applies to business development. I have written before about how important it is to stay hungry, but not desperate, for new business. And as others have noted, you should frequently assess what you are doing that has not been working, and refocus your efforts elsewhere. Just as importantly, you should always assess exactly where your business is coming from, and try to expand on initiatives that have been successful. And, to my point, you should never be satisfied with what is working well; rather, you should seek to expand and improve on it.

When pursuing relatively few, high-stakes, or complex matters, you can spend a lot of time evaluating cases and making pitches to potential clients. When those prospects turn you down, it’s easy to write them off in anger and turn your attention elsewhere. After all, you might think, you have to spend time kissing frogs to find your prince. But be careful of falling back on a “sour grapes” mentality and convincing yourself you didn’t really want that client or are better off for not having been retained. Far more productive is to ask yourself what you might have done differently, and to take steps to improve your next pitch based on what you learned.

If I was turned down by a prospect, I would be inclined to say something like, “Even though I’m disappointed we couldn’t win your business, I appreciate the opportunity to meet with you. Might I ask who you retained? More importantly, can you share any advice on what we might have done differently or how we can improve our chances in the future?”

I don’t know if this approach is the right one or not, but for better or worse it’s how I would be inclined to respond to rejection; namely, try to gain value and improve for next time.

Some of the best advice I received with regard to networking is to mine your contacts for further contacts. Again, this requires an insatiable appetite for new business; a refusal to be satisfied. When I make a great new contact, my instinct is to lay low and not risk offense. But I try to overcome that instinct and, instead, politely inquire whether the new contact can introduce me to anyone else who might value my firm’s services. In my experience, if you do that, you are sometimes pleasantly surprised by the good results, and you never regret it. I’ve never had anyone react negatively to my request for further contacts; if anything, people have responded with encouragement.

I know some people who read this will think that refusing to be satisfied is a character flaw; a sign of a broken psyche. Perhaps it is. But refusing to be satisfied isn’t really about self-entitlement and ego; rather, it is an attitude that can directly benefit clients.

For example, in settlement negotiations, it sometimes pays to refuse to be satisfied. When I was a junior associate, I remember attending a mediation with an attorney named John Summers. He was the most tenacious negotiator I had (and have) ever seen. He demanded a dozen concessions, and when the other side capitulated on 11 of the 12, he doggedly advocated for the last one. It was nearly 7:00 p.m. on a Friday, everyone was exhausted, but John was unrelenting. I swear the other side gave in just so they could leave the building to get something to eat. To this day, I cannot believe the terms that John managed to obtain for our client; terms I never would have thought possible and terms that I imagine many lawyers would have been reluctant — dare I say embarrassed? — to insist upon.

That refusal to be satisfied has stayed with me, and its importance has become more apparent to me through the years. I remember working with a junior associate several years ago who was responsible for preparing the first draft of a motion. When I asked for her assessment, she told me she thought the brief was “good enough.” That comment has always bothered me. We don’t bill hundreds of dollars an hour to produce work that is “good enough,” and I frankly think we owe it to our clients to produce work that is perfect. We cannot ever reach that goal, of course, but that is why we continually strive to do better. We’re never satisfied.

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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