INTRODUCTION
Easy victories enhance morale, develop your reputation, give you momentum, and, most important, do not cost you much. — Robert Greene
The supreme art of war is to subdue the enemy without fighting. — Sun Tzu
It is unwise to engage in large-scale legal conflicts that are not necessary to achieve victory. When the environment is right, settlement is not just an option, it’s the optimal resolution. This article borrows heavily from strategies of warfare observed, developed or explained by those quoted.
Why warfare? Litigation is conflict. Your goal in this conflict is not to fight, it’s to win. This is achieved by forcing your opponent to bend to your will or to break them by force of law. You act to instill fear, rational or irrational, that their defeat is imminent and unavoidable. If that cannot be accomplished, you act by overcoming their defenses and overrunning them at trial. It’s coercion by way of the rule of law instead of force of arms. It’s non-violent warfare with its own conduct rules and ethics appropriate for the conflict. The combatants in litigation are the trial lawyers.
Trial lawyers are well-known for trumpeting that they are trial lawyers. They live to go into courtrooms in the face of injustice and right the wrongs experienced by the people they represent by way of trial by jury or judge. They train to master the rules of evidence, criminal and civil procedure, and the art and science of storytelling and persuasion. The great one’s study strategy and tactics, they train and collaborate with other great trial lawyers, and they practice. They also never stop learning, adapting, and creating new legal theories, litigation and trial strategies and tactics. They are innovators. The goal is mastery. The work towards mastery, at its most basic level, is punctuating the discipline it takes to get to and remain on the forefront of the profession. When a trial lawyer reaches for this pinnacle, that lawyer is substantial and worthy of a fearful respect.
Yet, even that lawyer, a Goliath-like figure, knows when full scale war is not necessary to achieve victory. And, not only is expanded conflict not necessary, it’s counterproductive, time-wasting and otherwise inefficient. The trial lawyer will settle cases, but under their terms. How do they do it? They know settlement isn’t luck or compromise, it’s the product of effective application of strategy.
CASE SELECTION: CHOOSE YOUR BATTLES WISELY
“We have limitations – our energies and skills will take us only so far. You must know your limits and pick your battles carefully. Consider the hidden costs of a war: time lost, political goodwill squandered, an embittered enemy bent on revenge.” — Robert Greene
Getting people to call you for help is the lifeblood of any plaintiff oriented civil law practice. If you don’t get cases, you have no work. But you can’t help everyone that will call you. Not because you lack any desire to do so, but because our laws aren’t designed to right every perceived wrong. This is a lesson it took me an inordinate amount of time to learn. I am empathetic by nature and a sucker for causes, and in some instances the weird and unconventional story. Such is the life of a plaintiff’s civil rights lawyer. But I needed to implement gatekeeping tactics to stop myself from taking on too many at one time or taking up true lost causes.
Even the largest plaintiffs’ firms don’t have unlimited war chests for cases with hotly contested liability or scant damages. Taking too many has consequences. You lose time, perhaps your greatest asset as a human being. Time that can be spent with loved ones, with friends, and working on cases where you can make a real difference in someone’s life.
You expend resources that you may not get back. Plaintiffs’ lawyers routinely advance the costs associated with litigation, for several reasons. Primarily, the people that come to you typically cannot afford to pay out of pocket to advance their case. Litigation is expensive. Deposition costs, expert fees, travel, etc. If we don’t provide that service, most people would not have viable cases no matter how well the law is positioned to help them. It also gives you “skin in the game.” You must perform due diligence to make sure the use of those substantial resources goes towards a probable, tangible accomplishment. Finally, your reputation can shift based on the cases you accept. Judges notice when bad cases get into their courtrooms. Other attorneys notice what kind of cases you bring. Jurors know when their time is being wasted. To borrow an often-used phrase, “the juice must be worth the squeeze.”
Applying these principles is easier said than done if you are short on work. Nevertheless, trust me, don’t talk yourself into a case because you simply feel you aren’t busy enough or because you think you can change the world. Once you figure out how to get people to call you about their cases, case selection is the most important part of the business of the private practice of civil litigation, and the most important factor in getting a case settled.
Identify and acknowledge the unsuitable client.
Careful case selection should consider who you will be representing. You are not judging their worth as a human being – you are assessing whether you can partner with them in litigation. Interviewing your person before signing them up should not solely be for evaluating the nuts and bolts of their claims and damages. If something rubs you the wrong way during the interview, listen to the alarm in your head.
I recall a case years ago involving a person that called to tell me he was assaulted by a store security guard in a display of unapologetic racism. I was in, that’s my kind of case. Signed him up, sent a nasty letter to the store, and started collecting my evidence. Luckily, the first pieces of evidence I collected after I sent the letter were photographs sent by the client of his injuries. In addition to the small bruise on his head, the photograph showed a white male with Nazi face and neck tattoos. Turns out the security officer was a black man who had taken some verbal and racist abuse from the potential client before the client was escorted out of the store. The “assault” made more sense, and I quickly made my exit from that matter.
If you have a personality issue with the person looking for help, you do them a disservice by taking their case just because you think it will be a potential check. It’s the same concept you ask jurors to think about during jury selection, and the same concept you expect your potential clients to apply to you. Not every case is for every juror. Not every lawyer is for every person. Similarly, you need to acknowledge that not every person is for you. If you sense something unsuitable, whether it’s a personality conflict, clearly unreasonable case resolution expectations, concerning instability, don’t do it. If you sign on to help in that situation, you will be an impediment to resolution of the case, or you are simply setting yourself up to “fail” someone who mistakes you for a miracle worker. And don’t feel bad. Not every lawyer follows this advice, so rest assured the person will find a lawyer.
Additionally, be wary of the person looking for your help who doesn’t want to participate in their own case or tries to keep information that you need from you. Litigation is collaborative. The person you are trying to help is the star of the show, and an absent star will make for a cancelled (jury rejected) show. These folks, in my experience, also tend to be the least grateful for your work and effort to help them.
The Professions Unicorn.
The crown jewel of all cases. The case where liability is clear (or accepted), your human being is an incredible person, their harm is significant, and there is ample coverage. Take that case and settle it efficiently. If it doesn’t settle it’s because the party responsible unreasonably under-evaluates the extent of harm or makes frivolous liability arguments. Wasting time and money on depositions, experts and the like eats into resources meant to care for your human. If you are working on a contingency basis, there is no reason on your end to extend a case that can and should be settled today. If you have been hired at an hourly rate, unnecessarily extending such a case is unethical. After thorough review of your person’s damages, confirming the responsible party’s insurance coverage, and addressing collateral issues (subrogation/reimbursement issues for example), the trial lawyer gets this case resolved by way of settlement. If the case doesn’t settle the other side is making a tremendous mistake, opening their client to a potential excess verdict and (if at the direction of a defending insurer) opening their coffers for engaging in bad faith after getting beat soundly at trial.
Every other case.
If the unicorn does not come knocking on the door, your cases are going to have some contested issues or combination of such usually concerning liability, damages, and coverage. In cases with multiple defendants, finger-pointing routinely occurs between defendants for you to sort out. There may be arbitration agreements. Defendants sometimes hide available insurance. How do you get those cases to settle? Assuming you haven’t taken a true lost cause, in tandem with application of the principles expressed below, you will have opportunity to get your cases to an appropriate settlement.
GET YOUR MIND RIGHT
“In the heat of battle, the mind tends to lose its balance. It is vital to keep your presence of mind, maintaining your mental powers, whatever the circumstances. Make the mind tougher by exposing it to adversity. Learn to detach yourself from the chaos of the battlefield.” — Robert Greene
If litigation is a form of warfare, the combatant needs to be in the right state of mind for the fight to come. Said differently, you need to practice controlling your emotions. A lawyer who is emotionally unhinged easily and voluntarily is an easy mark. That person can be manipulated, thrown off balance, and ultimately rendered next to harmless. If you give in easily to emotions such as anger/rage, sadness, and despair you will make unwise decisions in settlement discussions while under the influence of those emotions. Expect your opponent to maneuver you into those states of mind as often as you will let them.
Instead, as Greene teaches in his book 33 Strategies of War, look at things as they are, not as your fear has colored reality. We suffer occurrences in our mind that routinely do not reflect reality. Fear can be paralyzing. It is difficult (I speak from experience) to learn to overcome those thoughts. But it can be done. It is an exercise in deep self-reflection and an objective evaluation of events. Evaluate other people by their actions, not their words. We deceive one another best with our spoken language. Actions and reactions to events tell so much more about your opponent than the message they want to speak to you. Declare war on yourself and your irrational fears, then stop being controlled by them. Get to a state of mind that will allow you to make good decisions, to be an effective strategist.
KNOW YOURSELF AND YOUR ENEMY
“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.” — Sun Tzu
What are your strengths and weaknesses as a lawyer who has entered settlement discussions? Have you given any serious thought to that question? I used to look at settlement as a negotiation. Every side gives up something to get the case done. Every side leaves the mediation a little unhappy. In my early years, I spent time reading “how to negotiate” books. I was not a confident negotiator. I thought it was because I didn’t know how to negotiate and I didn’t enjoy the process. I would sit in all day mediations wondering what the hell I was doing there. Why was I coming off my numbers? Why weren’t they coming up to a number I considered reasonable for the case? Why was I struggling with these questions in my head? Why did I not enjoy the process?
After some lengthy reflection, I figured out my problem wasn’t my skills in negotiating. It was my comfort with the facts in my case. Not facts associated with the liability questions typically (though when you take up causes that can certainly be an issue), but facts associated with the person I was there to help. While empathetic, I don’t instinctively feel comfortable getting into other people’s private lives. So, I wasn’t digging in enough to get to know them or the degree of impact the harm caused. As a result, I was uneasy communicating why my settlement number was right for my person because I didn’t have a handle on the “right” number. I thought professional boundaries are important to keep with my “clients.” I fell into the trap of tying my person’s actual, experienced harms to the amount of their medical bills. I acted accordingly in my negotiations. Don’t do that. If you do, you will go into a mediation or settlement discussion with unnecessary anxiety, and you will impair the prospect of a settlement that reflects your person’s harm. Get to know what really makes you fearful and anxious in litigation. If you are vicious with your self-reflection, you will find where your cases’ real weaknesses lie. It’s usually in work you have not performed to find the necessary confidence in the case.
Also, you should not look at settling a case as a negotiation. You aren’t there to give anything up. Settlement should be looked at as an opportunity for the other side to pay your person the amount of money that meets the gravity of the injuries and consequences they experience. The human loss part of this payment is part atonement. And settlement allows the party or parties responsible to atone as soon as possible. On the other hand, if settlement occurs because you feel pressure to “negotiate” to stop the bleeding in a case you think is going the wrong direction, you’ve picked the wrong case or you’ve given into irrational fear. Such things will lead to unpleasant execution of an exit strategy. In sum, stop negotiating. Instead start providing meaningful opportunity.
Self-knowledge though means little unless paired with a clear view of your adversary. I hesitate in the current political atmosphere to call the other side in civil litigation an “enemy” for fear of sounding overly aggressive, but that is what they technically are. Enemy does not necessarily mean evil; I am using it to describe someone who is working against you, thwarting you. Their motivations and goals are contrary to yours. They are the generals directing the opposing force. In litigation, they are charged with developing strategies and tactics to weasel out of responsibility for the harm caused to your person.
Some adversaries take that task more seriously than others. I’m talking about the lawyers and insurance adjusters you will face (though finding out everything you can about a defendant is a must too). Get to know them. Ask your colleagues what insurance companies fairly adjust claims and which don’t. Pull trial tapes of the defense lawyers your cases are assigned, find their verdicts, pay attention to their actions in the various cases you have against them, ask other lawyers about their experiences with those people (the plaintiff bars in Kentucky and Ohio are second to none), pull depositions they have conducted with both lay and expert witnesses.
Be aware of the assholes in the profession. Those that engage in what Robert Greene refers to as unconventional, or “dirty,” warfare. I was recently reading about a plaintiffs’ counsel in Texas who died unexpectedly. Defendants’ lawyer knew of the death and mentioned it to the trial court. But defendants simultaneously filed a summary judgment motion that wasn’t served on plaintiffs (their counsel had died, of course). When new counsel for plaintiffs appeared two weeks before the summary judgment hearing, defendants’ counsel opposed the requested continuance. Oddly, the trial court proceeded and granted summary judgment. Luckily, the Texas Court of Appeals reversed. Lesson? If your adversary is a special kind of awful, you need to know.
Finally, keep this in mind: the fear of the case-eating monster you think lurks around every corner is experienced by the other side as well. I cannot provide a better example of this concept than U.S. Grant’s recollection of his experience at the 1862 Battle of Corinth in the American Civil War.
“As we approached the brow of the hill from which it was expected we could see Harris’s camp, and possibly find his men ready formed to meet us, my heart kept getting higher and higher until it felt to me as though it was in my throat. I would have given anything then to have been back in Illinois, but I had not the moral courage to halt and consider what to do; I kept right on. When we reached a point from which the valley below was in full view, I halted. The place where Harris had been encamped a few days before was still there and the marks of a recent encampment were plainly visible, but the troops were gone. My heart resumed its place. It occurred to me at once that Harris had been as much afraid of me as I had been of him. This was a view of the question I had never taken before, but it was one I never forgot afterwards. From that event to the close of the war I never experienced trepidation upon confronting an enemy, though I always felt more or less anxiety. I never forgot that he had as much reason to fear my forces as I had his.” — U.S. Grant
FORGET WHAT YOU DID IN PAST CASES
“What often weighs you down and brings you misery is the past. You must consciously wage war against the past and force yourself to react to the present moment. Be ruthless on yourself; do not repeat the same tired methods. Wage guerilla war on your mind, allowing no static lines of defense – make everything fluid and mobile.”
“The more we lose ourselves in predigested theories and past experiences, the more inappropriate and delusional our response.” — Robert Greene
Being predictable is a liability, and an easy way to get manipulated. If you employ the same strategies and tactics in all your cases, you have made the possibility of settling your case harder. The defense will anticipate your moves and blunt your pressure. Litigation is not an assembly line. Instead, this area of the legal profession rewards creativity and imaginative application of skills to the unique experiences each person a lawyer helps. This applies not just to your settlement strategies, but also your trial strategies. If you try your cases in a cookie cutter/one size fits all manner, you are easier to defeat.
Your adversaries will then expect you to conform to patterns. Resist the urge to be repetitive. While no fan of his politics, Confederate general Thomas “Stonewall” Jackson was a brilliant military tactician. Prior to being shot and killed by his own troops, he made a routine in less than two years of routing United States military forces throughout Virginia during the American Civil War. Forces that were usually larger and better equipped than his. He understood this concept perfectly:
“Always mystify, mislead, and surprise the enemy, if possible; and when you strike and overcome him, never let up in the pursuit so long as your men have strength to follow; for an army routed, if hotly pursued, becomes panic-stricken, and can then be destroyed by half their number. The other rule is, never fight against heavy odds, if by any possible maneuvering you can hurl your own force on only a part, and that the weakest part, of your enemy and crush it. Such tactics will win every time, and a small army may thus destroy a large one in detail, and repeated victory will make it invincible.” — Thomas “Stonewall” Jackson
If you litigate your cases in conformity with your adversary’s expectations based on your past actions, expect poor settlement outcomes. Instead, don’t be a stationary target. Every one of your cases is unique, and each case deserves unique attention, and strategic and tactical thought. In litigation, as in war, the predictable general loses.
PREPARE – THEN PREPARE MORE.
“He will win who, prepared himself, waits to take the enemy unprepared.”
“Plan for what is difficult while it is easy, do what is great while it is small.” — Sun Tzu
There is no substitute for preparation in this equation. You can’t compromise on any of the points in this article in my opinion, but you certainly can’t compromise on this point. Preparation is the greatest settlement accelerator. You must know your case. Prepare such that you don’t just feel comfortable advancing your case towards settlement, but you are confident-bordering-on-convinced that what you are there to do is what must be done. When you know your case better than the defense knows theirs, you control the tempo.
Before you initiate the case, be thorough in your investigation. Meet the witnesses and be mentally present for those interviews. Collect every piece of evidence you can. Review documents, videos, and other tangible evidence multiple times. You will pick up something you have missed almost with every review. If the devil is in the details, make sure you find him, so he is the other side’s problem. Start discovering your person’s story immediately. Determine your adversary’s common tactics and how they practice cases. Visit the site of your person’s terrible experience. Get a feel for the sites, smells, sounds and feels. Evidence collection should be five-sense focused. Find out how much coverage is actually available. Consider focus group to identify weaknesses and unobserved case strengths. Preparation is not a phase, it’s a posture.
If you have prepared thoroughly and correctly, in settlement discussions there should be no argument you can’t meet with rebuttal, no fact that surprises or befuddles you, no power move undertaken by the other side that you aren’t ready for, and no rational reason (any reason not driven by your own delusional fear) why you should lose the position of advantage.
SPEED KILLS
“There are but few commanders who properly appreciate the value of celerity.” — Thomas “Stonewall” Jackson
“In a world in which many people are indecisive and overly cautious, the use of speed will bring you untold power. Striking first, before your opponents have time to think or prepare, will make them emotional, unbalanced, and prone to error.” — Robert Greene
Sure, not every case can be settled within weeks or months of acceptance. I think typically that only happens with the unicorn cases described above. Instead, we are usually forced to wait on medical record and bill requests to come in, sometimes permissions or court orders are needed to investigate incident sites, defendants need to be located, and most importantly the extent of our injured person’s harm needs to be clear.
The point, though, don’t be the reason there is delay. As a plaintiff’s lawyer, you will have the opportunity to make the first move in the game. Get records requests out immediately, take the necessary steps to investigate right away, have preliminary discussions with experts as soon as possible if necessary, and regularly check in with your person to see how they are doing. Create a well-thought-out plan for advancing your person’s claims. Having your case in a position to settle as soon as practicable, and in a position to rapidly transition from settlement state to trial state is ideal in the event the other side engages in dirty tactics, misevaluates your person’s harm or simply isn’t prepared. When the other side sees that you are in fact ready to face a jury, and they are not, their anxiety will be palpable, and you will discover you have created leverage.
NEGOTIATE WHILE ADVANCING
“Before and during negotiations, you must keep advancing, creating relentless pressure and compelling the other side to settle on your terms.” — Robert Greene
“No terms except immediate and unconditional surrender can be accepted. I propose to move immediately upon your works.” — U.S. Grant
Don’t allow the settlement discussions to turn into absolute cease-fires. Remember the part about great trial lawyers and their desire to try cases? Strategizing for settlement does not mean you stop preparing the case for trial. Even if one of your purposes for settling a case is the efficient use of resources, you can continue to advance your case when settlement discussions begin.
Action and movement are superior to inaction and stagnation. This is the concept of momentum. It is certainly fine to take brief pauses to reflect, re-evaluate, and reconsider current strategies and tactics. But pauses can turn into significant time gaps, the length of which can get away from you and will stifle momentum and will cost you ground you have already won.
For instance, entering settlement discussions doesn’t mean you can’t file offense-oriented, dispositional motions if you have the ammunition. The message to the other side should be clear. If the case doesn’t settle, you’re escalating the conflict and that will not be a good thing for them.
U.S. Grant was not successful in his professional life prior to the Civil War, at one time selling firewood on the streets. But when the United States entered armed conflict with southern rebels, he knew how to end the fight: constant pressure and forward-driven movement. As the American Battlefield Trust has pointed out, he is the only American general to force unconditional surrender on three enemy armies.
In 1862 he took Fort Donelson on the Tennessee River under such terms. The confederates defending the fort didn’t just give it to him. Instead, following his victory at Fort Henry, Grant gave himself an aggressive deadline for taking Donelson. He didn’t meet the deadline because of conditions out of his control, however, his use of momentum did two important things. It allowed him to surround the fort, and after a spirited but unsuccessful breakout attempt by the confederate defenders he instilled in the confederate’s command a sense of hopelessness. As a result, they sued for peace and sought terms. Grant would give none except immediate and unconditional surrender. If they didn’t accept, he would come for them. This action stunned his opponent, a friend of his before the war. There was nothing Grant’s opponent could do though. Grant had him, and his terms were accepted. Keep advancing, working to encircle your opponent, even when discussing settlement.
CONCLUSION
“The victorious strategist only seeks battle after the victory has been won. While he who is destined to defeat first fights and afterwards looks for victory.” — Sun Tzu
Litigation is non-violent warfare and when engaging in it, you should think and act like a general operating in war. In other words, have a plan that you have steadily, properly and thoroughly thought through. Doing so will put you in the best position to get your cases settled when they should. The suggestions above are not meant to be exhaustive. In fact, I would prefer you to be in your head right now pointing out things I did not mention and expanding on these concepts in your own way. The overall purpose of this article is to demonstrate successful resolution of your cases by way of settlement depends primarily on you. You are responsible for picking the battles worth fighting. You are responsible for getting your mind right. You are responsible for coming up with fresh strategies and tactics to get justice for the people you sign up to help and then implementing them rapidly, confidently, and competently.
ENDNOTES
- Robert Greene, The 33 Strategies of War (Viking Press 2006), Strategy 1 (“The Polarity Strategy”).
- Sun Tzu, The Art of War, trans. Samuel B. Griffith (Oxford University Press 1963), Chapter 3 (“Attack by Stratagem”).
- Robert Greene, The 33 Strategies of War, Strategy 1 (“The Polarity Strategy”).
- Robert Greene, The 33 Strategies of War, Strategy 6 (“The Guerrilla-War-of-the-Mind Strategy”).
- Sun Tzu, The Art of War, Chapter 3 (“Attack by Stratagem”).
- Robert Greene, The 33 Strategies of War (Viking Press 2006), Strategy 5 (“Avoid the Snare of Groupthink: The Unconventional (Dirty) War Strategy”).
- Ulysses S. Grant, Personal Memoirs of U.S. Grant, Vol. 1 (Charles L. Webster & Co. 1885), pp. 330–331.
- Robert Greene, The 33 Strategies of War, Strategy 6 (“The Guerrilla-War-of-the-Mind Strategy”).
- Quote attributed to Thomas “Stonewall” Jackson; see e.g., James I. Robertson, Stonewall Jackson: The Man, The Soldier, The Legend (Macmillan 1997), p. 297.
- Sun Tzu, The Art of War, Chapter 10 (“Terrain”).
- Sun Tzu, The Art of War, Chapter 7 (“Maneuvering”).
- Quote attributed to Thomas “Stonewall” Jackson; see Robertson, Stonewall Jackson, p. 297.
- Robert Greene, The 33 Strategies of War (Viking Press 2006), Strategy 18 (“The Blitzkrieg Strategy”).
- Robert Greene, The 33 Strategies of War, Strategy 15 (“Control the Dynamic”).
- Ulysses S. Grant, Letter to General Simon Bolivar Buckner, February 16, 1862, in The Papers of Ulysses S. Grant, Vol. 4, ed. John Y. Simon (Southern Illinois University Press 1972), p. 367.
- https://www.battlefields.org/learn/articles/ulysses-s-grant-myth-unconditional-surrender-begins-fort-donelson
- Sun Tzu, The Art of War, Chapter 4 (“Tactical Dispositions”).




