Alan Dershowitz, Associate Advice, Rudeness, Small Law Firms

Small Firms, Big Lawyers: Five Tips for Dealing With Obnoxious Opponents

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….

1. If they get to you, they win.

This was a common scenario for me early in my career. I’d have some dust-up with a jackass of an adversary who would manage to get under my skin. Then I’d get home in the evening and find that I was still thinking about it. I’d be sitting on my couch, replaying the conversations in my head, working myself back into the same lather that I had going earlier at work. If this happened at bedtime, I’d have trouble falling asleep, obsessing over how to get back at my opponent. Not a good use of my time.

Then one day, after a particularly frustrating donnybrook, I realized that I was making a big mistake. I was sitting on my couch, shaking with rage over the injustice of my adversary’s conduct. And then I wondered what he was doing at the same time. And it occurred to me that he was probably watching the ballgame, drinking a beer, and not thinking about me or our case. By letting the other guy cause me to have this reaction, I was letting him win. And that annoyed me, because I don’t like losing. Stewing over my interaction with jerkwad opposing counsel was a form of losing. So I decided not to do that anymore.

Don’t get me wrong; it still takes some effort. I still get tweaked by the actions of my adversaries. So I often have to remind myself not to let them get to me. But by keeping that in mind, I learned to spend less time worrying about them. That single decision made litigation more fun.

2. Smile, or better yet, ignore them.

Many litigators, especially seasoned ones, try to get your goat on purpose, understanding the tactical advantage that they can garner (see point 1). You can often see the signs by looking at their website profiles, or learning about their reputations in your community. They’re usually the ones who boast about being tough and aggressive and hard nosed. Many of them learned this style from their old-school mentors, who practiced litigation as bloodsport. It’s a point of pride with them. Often, they use this tactic to show off in front of their clients, especially at depositions.

Showing them that they don’t bother you is the best way to counter that tactic. Again, I’m not saying this is easy. Over time, I’ve learned to notice when an opposing counsel is raising my blood pressure. Anger causes a physical reaction, such as a quickening of the pulse and a rush of adrenaline. Keeping track of your reaction affords you the opportunity to head it off. Then, instead of showing your pique, you smile back at your opponent, maybe with a slight degree of a knowing condescension. It’s very off-putting for someone who’s trying to rattle you. It can even be embarrasing for her, especially if she’s puffing for her client. All of a sudden, she’s the one who looks rattled.

And ignoring someone who’s posturing for attention is even more effective.

3. Always fight up. Never fight down.

This is a nice piece of advice often attributed to Ronald Reagan, although lawyer extraordinaire Alan Dershowtiz credits his father with it. Basically, it means that you should only bother to tussle with people stronger or better than you, instead of with weaker opponents. When you fight someone stronger, you really can’t lose: if you win, you’re David defeating Goliath; if you lose, well, your opponent was stronger. On the other hand, you really can’t win by fighting someone weaker.

Getting into it with opposing counsel is a tacit admisssion that he or she is worthy of your combat. Why give that up? Getting into the mud with your opponent just brings you down to that level.

4. Have compassion for them.

It might not be an intentional gambit on your opponent’s part. It’s possible that he can’t help himself. You need to allow for the possibility that there literally may be something wrong with him.

There’s one litigator I’ve dealt with who has made me angrier than any other. Everything he did pissed me off: blowing deadlines, misrepresenting my statements and actions to judges, going after people I care about, violating court and ethical rules, screaming at depositions. But after watching him close up in one case that lasted nearly two years, I came to realize that he’s a few sandwiches short of a picnic. He’s not stupid. And I’ve started to realize that he might actually not be truly sinister. Instead, he’s really more of a mess. That realization made me look at him in a different light.

Put it this way: Someone who swears at you because he’s a jerk is worthy of your contempt. But someone who swears at you because he has a serious mental disability like Tourette’s syndrome can’t help himself, and is worthy of your compassion.

Or maybe your opponent isn’t mentally unstable; maybe he just doesn’t know any better. That might not be his fault. Feeling sorry for your opponent might just be the way to go.

5. Believe in professional karma.

It’s perfectly natural to want to get back at someone who’s wronged you. Unfortunately, the opportunity often never arises. Lenient judges often give a pass to your rule-breaking opponents, instead of delivering the comeuppances they deserve. Or the case settles before you have a chance to deliver a courtroom smackdown.

Don’t worry about it. In my 17 years, I’ve learned that there’s such a thing as professional karma. What goes around does indeed eventually come around. You might not get to be the one who gets back at your SOB opponent. But down the road, if he keeps acting that way, he’ll find himself sued or disciplined or saddled with a career-handicapping reputation, and you can take pleasure in that. Patience, Grasshopper.

Litigation can be fun, if you don’t let the bastards get you down.

Updated: A reader emailed me taking issue with my characterization of Tourette’s syndrome as a “serious mental disability.” It is indeed a mental disability protected by the Americans with Disabilities Act, but it is not necessarily a “serious” one. I’ve corrected the reference. — JS

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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