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September 01, 2015

Learning Good Judgment

Here are some guidelines to developing this skill that is crucial to success as a litigator.

Robert E. Shapiro

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Litigation is a curious business, isn’t it?—a strange combination of past, present, and future. The immediate focus is on something that already happened. It will be adjudicated by current legal standards. But it depends decisively on predicting and controlling the future. A litigator must look ahead, and foretell and manage the ups and downs, the ins and outs, of the dispute—from the very first day the matter arises to the day when, one way or another, it is resolved, with a stake through its heart.

The habits necessary for navigating the yesterdays and todays of litigation are learned early on. Every young litigator coming out of law school should already know the law, or at least how to find it. So too, she should become comfortable very soon with managing the day-to-day docket of court deadlines and routine hearings. It takes a little longer perhaps to learn how to build a sound factual record. But this kind of sleuthing can be fun and has now become far easier, if perhaps more tedious, given how email provides a nearly verbatim account of what took place. So, before long, most young litigators will have the necessary tasks of the first two elements of litigation well in hand.

This is not to say there are no real skills to master here. Courtrooms, not to mention docket clerks, follow their own special etiquette. You learn fairly soon that there is every reason to treat court personnel and court reporters with special courtesy, given how useful it can be to have them as allies. As for record building, you must forget the received wisdom of the rest of the world. A good record builder knows hindsight is never 20/20 but rather equal parts poor remembrance, prejudice, and wishful thinking. And when it comes to your client, you must trust but verify. In two or three years’ time, though, most young lawyers are aware of the booby traps and adequate to the task of building a fair summary of the critical facts.

It is the final piece of the puzzle—managing the future—that is wanting most of the time. It is not enough to know the law and the factual record. A good lawyer needs to know what to do with these bits of understanding as the case moves forward. This kind of special foresight we call good judgment, and it is always in demand.

A lawyer without good judgment, no matter how well he can build a record or knows the law, is of no more use than a racecar with a tipsy driver, whereas those who have it in abundance can sometimes turn a jalopy into a winner. But what is good judgment exactly? And where does one get it? Both questions are important, but neither can be answered simply.

In fact, they present a troublesome problem. False images of good judgment abound, and many young lawyers have the suspicion, even the worry, that they will never get it, no matter how hard they try. In the most basic terms, good judgment seems to be, or to be about, making good strategic decisions about a case or dispute as it progresses. How might you learn to do that? An excellent first step would seem to be to find a good mentor who can teach you by rule or example. But how does one distinguish the experts from the charlatans? Success might be one criterion, but it is a flawed one, as we all know lawyers who seem frequently to succeed through pure dumb luck. The facts, too, have a lot to say about who succeeds and who doesn’t. And even with a capable mentor, how do you know you’ve got what he has? And what is it he’s got? Don’t say you know it when you see it, because maybe you don’t.

Can Judgment Be Taught?

Can judgment even be taught? It thrives on its own flexibility and resourcefulness in the face of ever-changing circumstances. It therefore cannot be a matter of hard-and-fast rules. What is there to teach? But neither does experience seem enough. Many seasoned litigators seem rather clueless. They never learn to make good judgments. There is the old joke about the lawyer who tells a client she should hire him because of his good judgment, and when the client asks the source of his good judgment, he responds: “years of experience making bad judgments.”

So does one have to be born with it—a talent for practical decision making? Some lawyers, no matter how intelligent, seem never to make progress or even to retrogress. But if it is not teachable, or learned by experience, or simply a matter of native ability, where does it come from? And how do you know when you have it?

The matter is not hopeless. The truth is, of course, that judgment requires all three at once: talent, experience, and natural gifts. And if it cannot be taught, it still seems something that can be learned. It develops slowly, with constant thinking and experimentation. It is the right kind of perspective, not a set of principles but an attitude. It is what the great philosopher Aristotle called a hexis, not so much a habit (as it is often translated) but a “way of doing.” It is a way of conducting one’s business, as much style as substance, but then substance too. It surrounds and infiltrates a litigator’s whole being. Part of learning judgment is learning that there is no formula and no principles that govern it. A good litigator’s habits must be acquired but never become entrenched, always being open to question, to being re-learned and reconsidered. Part of good judgment is the constant recognition that no one’s judgment is ever good enough. There are always mistakes, and it can always be improved.

Is there any more to say? Without a certain trope to follow, must a young lawyer merely launch herself into the world, eyes wide open, but always uncertain and without resource, hoping for the best? Well, there are some guidelines that can help, some general themes to consider. Again, not rules. Judgment defies rules. Indeed, it can be ruined by them. There are characteristics, attitudes, of good judgment—ways of thinking and doing that can put you in a good position to succeed, or at least not completely fail. None always applies. Some things that work in one case may even be contrary to what is good judgment in another. Any list of characteristics is bound to miss or ignore matters of importance. But here are a few guidelines to consider in learning good judgment.

1. The “vision thing.” Look broadly. Most first-year litigators get asked to handle individual projects: research memos, document collection and review, maybe some letter writing or simple motion drafting. All good skills to learn. But their focus necessarily is too narrow. Litigation is not about projects, or really even about cases. Sure, there is probably a lawsuit lurking somewhere in the matter, whether filed or threatened or being considered. But even if, as you progress, you begin to be involved in the case more generally, you are still not there. You may strategize some, or do some of the planning. But none of this is the heart or the basis for learning judgment.

Judgment asks this question: What problem are you trying to solve? What is the underlying difficulty that is being channeled through the lawsuit? And how might that problem be resolved? Lawyers who cannot see that forest for the trees, or perhaps do not know the forest is even there, cannot make good judgments about what to do or when to do it or whether to do anything at all. To be successful, you need to know what really is at stake, in the broadest terms, as you manage the issues. Seeing the big picture helps you find the smaller nubs that get to the heart of the dispute, leading more easily to a strategy for its resolution.

Seeing the matter as a problem, rather than a project or a case, allows you to see the matter in clear perspective. Trade-offs, cost/benefit thinking, compromises, all of which permit the good not to be swallowed by the unachievable best, become second nature. Nonsense rhetoric reveals itself. You learn to be skeptical of stock phrases or excuses like “a sign of weakness” or “always be aggressive,” or reflexive action such as the temptation to do it because the other side is doing it. Be smart. Figure out what will best move you forward to a resolution of the problem.

This includes thinking about what a solution might look like. Litigation is not played on a football field where the goal line can be seen in the distance 100 yards or fewer away. You cannot always succeed by simply plowing forward or even launching a long bomb, let alone a “Hail Mary.” There are lots of ways of succeeding. Does it only take the form of a trial victory? Summary judgment? Settlement? If the last, a settlement providing what? You will need to adjust your tactics, and maybe even your (and your client’s) expectations, as you go along.

2. Name that tune. Melodies stick. There’s nothing like a tune to be impossible to get out of your head. Your case needs a memorable theme song. A case without a theme is like a story without a moral, or a point. It’s bland, it’s boring, it’s forgettable. You need a compelling, persuasive, and brief account of your case and why you should win it.

All of your activities should hover around or be variations on that theme. Every letter to the court or opposing counsel, every brief, every in-court statement should sound it. Be careful not to be procrustean. The theme must both be broad enough to permit some alteration or modulation and cohere with a reasonable interpretation of the facts. Flexibility is key. New events, previously undisclosed documents, unexpected witness testimony may require you to adjust. But everything must be synthesized into a continuing theme that persuasively argues your side of the matter.

3. Manage the future by looking backward. This guideline does not refer to the facts, which you must know like the back of your hand, but to your tactics as you proceed. Know your vision and practical objectives, and how the problem can best be resolved. Look backward from that vantage point to today. How does what you are doing today advance the litigation toward that objective? If it isn’t doing so, can it? There should be no wasted effort. Always ask yourself “what’s the point?” Why take this deposition or pursue this motion or another? What will this deposition do for my case? If you cannot articulate it beyond “I think it will help,” it probably won’t.

As you prepare to take that deposition, make yourself identify the five or 10 specific bits of testimony you hope you can elicit. Then build a pathway toward them. Sometimes they may consist of key admissions. More frequently, you should be securing the means of controlling the witness and the testimony in later proceedings so that the facts will appear in the best light. “Killer” documents or “smoking guns” seldom have any business showing up in a deposition, unless they need to be authenticated. The trick is to be able to use the most powerful documents to maximum advantage later by closing off routes of escape.

4. Patience isn’t a virtue; it’s a necessity. Litigation takes time. Problems, even without an actual lawsuit, seldom go away or get solved overnight. You cannot rush it. Sure, you can attempt to keep things moving forward with all deliberate speed. But a lawsuit, in particular, has its own time and timing, and you should endeavor to feel out what it is. A federal judge trying to settle a case once summoned the opposing parties from great distances to a mediation and then dismissed them abruptly after their brief opening presentations. “This case isn’t ripe yet,” he asserted. Let your case ripen, under your careful eye, of course.

A corollary to this is to take things in stride. Seldom will a single motion or a particular deposition or hearing amount to the be-all-and-end-all. Judgment requires patience. Clients will holler and complain about setbacks, your corporate colleagues will bemoan the long delays, your firm will be eager to get paid. But you need mostly to tune it all out. If your goal is clear and your theme well developed, time is on your side. You’ve planted the seeds, organized as you know they should be; let them grow and blossom. Need a little luck? As baseball’s Branch Rickey once said, “luck is the residue of design.”

5. Work hard and persevere. In the face of obtuse judges or unfair results, litigators sometimes wonder why they should work so hard on all their cases. What’s the point if the judge won’t read or listen? Or the facts stink? Back when the baseball season was only 154 games, it was said you were going to win 50 games no matter what you did and lose 50 games no matter what you did. It was what you did with the other 50 that really counted. But since you never knew which game was in which 50, you had to work hard in all your games all the time. Good advice for litigators too.

Never give up. Ulysses S. Grant was famous for refusing to turn his horse around once he set off in the right direction. He almost drowned once when he insisted on fording a river in the Oklahoma Territory rather than have to turn back. Remember: God put the eyes in front so you’ll look forward. You always need to be moving forward too, not allowing obstacles to stop your progress.

But determination should not be an excuse for stubbornness. Many lawyers with poor judgment simply refuse to give up on a losing argument. Don’t continue to kick the horse long after it is deceased.

6. Don’t panic, don’t gloat. Fortitude, or at least gumption, is necessary in another respect too. There are always ups and downs in litigation. You are seldom going to win everything, even in the individual case. You need to learn from your mistakes and at least as much from what went right. They all contribute to your understanding.

Why did you succeed or fail? Be honest. One of the hardest things in life is not to fool yourself. You may wish to crow about how your argument persuaded the judge, but admit, to yourself at least, when it really was dumb luck. Lawyers are experts in the game of dodging blame. But sometimes it is your fault. Be clear on this and why. Accept your mistakes. They are inevitable. A New York lawyer was overheard to say he never wanted to make a mistake. Reject such a fellow as your mentor. All lawyers make mistakes. If this lawyer didn’t, it’s because he blamed them on someone else.

A lawyer with good judgment knows how to learn from prior mistakes. Do not fret over mistakes made; just deal with any consequences. The goal is to avoid repeating the same mistakes but with full knowledge that you will likely make some new ones.

In litigation, the worm always seems to turn. Today your case is going swimmingly. But try not to get too comfortable. The next day may bring the discovery of a troublesome document or a witness who botches her deposition when you thought she would excel. You cannot control these things, except by not losing heart. Remember: There’s almost always a next time.

And if you win, don’t strut. It’s your job to win, after all. And you should know it wasn’t all you, anyway. Your colleagues were essential. The judge’s mood was important. A good document may have surfaced at just the right time. The worst thing a litigator can do is believe it was all his own doing. It wasn’t.

7. There’s more than one way to skin a cat. You will give it your best shot. But even with all the best planning in the world, you will fail frequently. Not giving up includes the resourcefulness to try something new. What works is not always just what’s obvious or even best. Consider all the possibilities. When you begin writing a brief, don’t accept your first approach as necessarily the right one. Write your introduction first and try it every which way. And if you think you’ve written something perfect, follow Mark Twain’s advice and tear it up.

8. Pay attention. Judgment is not a matter of what you learned in kindergarten. But it may be about what you were told in the third grade. It’s striking how frequently lawyers are just too smart for their own good, thinking they already know the answers and failing to pay attention. They don’t listen to what their clients tell them about the problem and so misunderstand it. They ignore witnesses’ answers in depositions, too eager to go on to the next question in their notes, and so miss vital testimony. They fail to notice what’s bothering the judge and thus misunderstand what is happening to their case. They ignore the ideas of their younger colleagues who, less hidebound, are so much more creative.

You need to be all in, watching, listening to, and considering all that happens. Litigation is a full-contact sport. It will exhaust you physically and overtax your brain. You must have a passion for it, for its larger issues and its individual points. As Yogi Berra might have said, litigation is 90 percent mental and the other half physical. And maybe “luck is the residue of desire.”

9. He’s your idiot. Judges will drive you crazy. They are often not smart. They are always overworked, or believe themselves to be. Some are downright lazy. They frequently make bad decisions. It may be satisfying to rail against a judge, pronouncing him an “idiot.” But remember, he’s your idiot. Figure out the judge’s quirks. Particularly helpful is if you lose something before him early on. Why did it happen? What bothered or blinded him? Try to account for it subsequently. You may be able to turn it into a string of victories. Never be satisfied with an explanation that merely blames the judge. He is a part of the problem you have to solve.

10. Don’t spit it out—ruminate. Hasty decisions undermine judgment. When cows chew their cud, they swallow, regurgitate, and chew again. Then they repeat the process. Time permitting, this is a good idea in litigation. Worry over your cases. Think of them when shaving, or in the shower, when you lie down and when you rise up. Don’t go forward until it feels right, or you run out of time. And if the latter, get more time.

11. It’s not a blunder; it’s a trick. The other side’s case is never as bad as your client would want you to believe or perhaps you believe. Never assume your opposite number does not know what she’s doing. It is an old saw that when your opposing counsel makes a manifest blunder, it’s probably not a blunder. It’s a trick. Or at least something about her case you do not understand well enough. Figure it out.

Put yourself in the other side’s shoes. Know his case as well as, better than, he does. Abraham Lincoln used to say he spent all his time studying the other side’s arguments. What will he say? What approach will she take? This not only prevents surprises, it tells you exactly what you need to overcome to get your summary judgment or trial victory. Study your opponent. He will reveal many things about himself and his case, often unwittingly. If your opponent accuses you of something you know you are not doing, chances are he’s doing it himself. Look for his “tells,”’ his giveaways.

The best lawyers know how to use their adversaries’ argument against them. Legal arguments depend on context. Change the context, and the argument itself changes. Understand what larger picture your adversary is trying to paint. Paint your own picture, setting a different context, and look for how you can use his own arguments against him.

12. If you are fighting monsters, you risk becoming one. The rules require courtesy and honesty. For good reason. Your highest allegiance as a lawyer is to the court, the system of justice, which exists to promote the peaceful resolution of disputes. You must stay calm and polite, and be truthful.

It’s also good policy. Anger interferes with judgment. Rudeness begets rudeness and may undermine your ability to obtain a favor you need or to explore a settlement possibility. Ignore your adversary’s rudeness. Dishonesty is the worst policy. Your own world will be better for it if you stay true to these first principles. Whoever spends her life fighting monsters risks becoming one. Don’t become one.

13. Think. ’Nuff said, except remember that this is judgment we are talking about. As the foregoing guidelines suggest, there is an endless series of possibilities. If you think you’ve gotten to the end of your thinking, it’s likely you’ve stopped thinking. Think on.

14. “It’s what you learn after you know it all that counts.” Earl Weaver, the famous baseball manager, knew what he was talking about. Which is that he didn’t. If you think you have it all figured out, you don’t. Recognize you never will. Judgment itself is an ever-evolving, never-certain, sometime thing. Keep at it. Someday you may wake up and find you have it. For the moment, anyway.


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Robert E. Shapiro

The author, an associate editor of Litigation, is with Barack Ferrazzano Kirschbaum & Nagelberg LLP, Chicago.