Many litigators have a bias against settlement. It’s understandable. There’s no glamor in settling cases. No one is ever going to make a TV show called “The Settler,” about a young but scrappy underdog lawyer who fiercely negotiates tough-but-fair settlement agreements and always remembers to allow a 21-day waiting period if the plaintiff is 40 or over. (On second thought … better call my agent.)

Forget TV and movies. No lawyer has ever come home with the exciting news about settling a lawsuit (at least, no defense lawyer). “Honey, I settled the Devens case!” “That’s great, dear. Now go mow the lawn.”

In the midnineties, I was a junior associate working on a contentious sexual-harassment case. While we were able to win partial summary judgment, the main claims headed to trial in federal court. During the negotiations before the trial, the partner from my firm had a conversation with the plaintiff’s lawyer, who was that sort of rough-around-the-edges attorney who prided himself on spending a lot of time in the courthouse.

Looking to put my boss in place, the guy took a shot at our firm’s litigation style. Here’s what he said …

With a contemptuous smirk, he said, “I know what your firm’s deal is. I looked you up. You try to win summary judgment, and when you don’t, you settle. You don’t try cases. You guys aren’t real lawyers.”

My boss David was pretty confident, and he didn’t take the bait. Instead, he out-tried the guy in court and defeated the main claims. (The jury threw the plaintiff a small consolation prize on a subsidiary claim, awarding him far less than we had offered long before trial.)

But think about what this guy was saying. That we weren’t real lawyers because we tried to win cases on legal grounds, and because we tried to resolve cases through settlement. Shouldn’t we have hung our heads in shame?

There is a machismo (irrespective of gender) that goes along with trying cases. And it’s ridiculous. Let’s look at the facts.

In Massachusetts, where I practiced, there are an average of 35,000 civil cases filed each year in the superior court. By contrast, there are only about 500 superior-court jury trials conducted each year. Now I’m no math whiz, but that works out to less than 1.5 percent of civil cases going to the jury. Some of the cases filed get resolved by motion practice, and the vast majority of them get settled.

In employment law, where I exclusively practiced, the trial numbers are even smaller. Since most employment cases have some form of one-way fee shifting (that is, the losing employer has to pay the winning plaintiff’s attorney’s fees), there’s even less reason to gamble on a jury verdict.

Now your jurisdiction might have different numbers, but probably not by much.

Bottom line: most cases settle.

Now I can already hear that cadre of soi-disant “real lawyers” beating their collective chests like they’re extras in Rise of the Planet of the Apes (in the making of which no monkeys were hurt apparently) about the value of being a true trial lawyer. I once was at a CLE seminar where one of the deans of our local employment bar said that if you ever have the opportunity to try a case, you should leap at it — they’re a lot of fun.

Fun? Yes, actually they are. But I’m pretty sure that my fun was not one of the guiding factors in my clients’ decision to hire me.

The truth of the matter is that your job as a civil litigator is not to win at all costs. Instead, it is to make your client’s problem go away. And making your client’s problem go away often involves settlement. The deal is to get a good deal.

This doesn’t mean you need to be weak about it. You’re better off negotiating from a position of strength. Let me give you another example:

About eight years ago, I represented a startup company whose founders had signed noncompetes at their previous company. The former employer hired the 14th-biggest law firm in the country to send them nasty letters telling them that they had to shut down; they hired me to keep that from happening. After reviewing the facts, I felt that I had a pretty good argument why their noncompetes weren’t enforceable under Massachusetts law. So I set about trying to negotiate a workable deal with my Biglaw counterparts.

My client had no interest in taking away customers from the other company, and the founders hadn’t taken any trade secrets away with them. Certainly we could work out an understanding where they could keep their doors open while assuring the former employer that they wouldn’t harm it. I worked the phones for several weeks trying to make a deal.

Then on the day before New Year’s Eve, I got a call directly from the lead partner representing the former employer. This guy had been practicing since before I was born, and he recently had been president of one of the major bar associations in town. He was a big deal, and he made sure everyone knew it.

He said that they were done negotiating and that they were going to file their lawsuit and motion for an injunction the next day (right before the holiday weekend). I said, “WTF?” (OK, this was before there was a “WTF,” but I’m sure I conveyed the same meaning.) He said that his client was done fooling around and that they no longer had interest in settling. They were going to file and serve their complaint the next day. I was disappointed, and said so. And then I said this:

“Write this number down: 93-5432.” (I just made up that number now, but I used the right one then.)

He said, “What’s that?”

I said, “That’s the docket number of the declaratory action I filed three weeks ago. I’m serving you within the hour. You might want to turn your complaint into an answer.” And I hung up.

I’d have given anything to listen in on the guy’s conversation with his client, explaining that we had ambushed them and beaten him to court. In the end, we won the case in court and defeated their request for an injunction. My client’s company is still in business today.

My point is this: you can have a position of strength and still try to resolve the case without going to trial. Just because you’re trying to settle your client’s matter doesn’t mean you’re weak. And it certainly doesn’t mean you’re not a real lawyer.

Real real lawyers worry about solving their clients’ problems, not whether a trial is going to be “fun.”


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 [email protected].


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