Every one of us carries a measure of optimism whenever we decide to undertake something. Undoubtedly owing to a cluster of deep-seated personality defects, I find I often see a glass as half empty. I don’t begrudge this aspect of my personality; it tends to make me a conservative investor and a boring gambler.

Most successful plaintiff lawyers I’ve worked with, however, seem more often than not to be glass half-full types. Let me clarify what I mean for the benefit of any readers who aren’t familiar with the American system of jurisprudence. I’m referring specifically to lawyers who agree to take on clients and cases on a contingency basis. Under these circumstances, a lawyer agrees to represent a client or clients in a lawsuit without any fees unless and until there is some recovery, by settlement or judgment. There is always an investment of the lawyer’s time and often the lawyer also agrees to advance the costs of litigation against the chance of recovery. If the case or claim is successful, the lawyer is reimbursed the costs she advanced and she also receives an agreed upon percentage of the recovery.

It’s not difficult to see how one would have to be something of an optimist to take any case on contingency, though a better quality case against a deeper-pocketed defendant tends to reduce the risk. In fact, some of the wealthiest practicing lawyers earned their fortunes through contingency fee litigation.

Not long ago, I handled a case against someone so optimistic about his client’s case that he was literally “drunk” on his own Kool Aid. So drunk, in fact, that he didn’t sober up until after he lost the trial and his client hired another lawyer to represent her in her appeal. It wasn’t that his client had a drop dead loser of a case. The case actually had some sexy facts; the kind of facts that can make jurors rock back and forth in their seats with interest. Things could have gone the other way, and he could have won. But it wasn’t that good of a case, and he could have and should have tried earnestly to settle before rolling the dice with the jury. He was just too buzzed to see the glaring weaknesses or put a realistic settlement value on the case. He never got within a range in which it made the remotest sense for my clients to make any serious offer–so they didn’t.

I recognize the counter-argument can seem compelling. After all, some of the biggest jury verdicts came out of situations in which David took on Goliath and prevailed against all odds. And I’ve already admitted I tend to see the glass a half empty. But what set my “drunkard” opponent apart from another, wiser lawyer was his steadfast refusal to give any weight to the opinions of two separate neutrals (a mediator he had selected and a USDC Magistrate Judge sitting as a settlement officer), who both told him he was being ridiculous in his expectations and wrong on a pretty important issue of the law.

Is it possible to be a “sober” optimist? Sure. One way is to pay attention if multiple neutrals (including one you selected) suggest you’re off the mark. Of course, neutrals may not always be truly neutral, even when you’re paying them to (i.e., when they’re leaning on you in a mediation). Another approach is to submit your facts and arguments, including what you expect the other side will say, to a mock jury–even a cheap one like I described here. I’ve also known lots of lawyers (even really skilled ones) who will ask every colleague they know what they think about a set of facts, just to see if they’re missing something. There’s nothing wrong with this, as long as you don’t inadvertently waive the attorney-client privilege.

One final thought: being a “drunk” optimist is fine: (1) as long as you’re gambling only with your own time or money; or (2) just like elective surgery, if you fully inform the client of all circumstances, including the risks (or likelihood) of walking away with nothing, and the client understands and is just as eager to roll the dice, then by all means roll the dice.

I asked several top Southern California mediators I know personally or by reputation to share their best “tip” for success at mediation. In exchange for their labors, I promised the prestige and notoriety of being featured on this humble but aspiring blog. Several neutrals cheerfully responded and provided some great tips. The following are the best 6 responses I received:

Jeff Kichaven (www.jeffkichaven.com): “Prepare, prepare, prepare.  Get your brief to the mediator a week before the mediation.  Give the mediator time to read it, think about it, read it again, and call you to discuss it.  That phone call – 10 to 20 minutes at most – can be the most important time in the whole mediation process.   Be sure to discuss:  (1) What are your biggest challenges in the mediation?  (2)  What are your expectations of the mediator?  (3)  What should the mediator know about the personalities of the participants?  (4)  Is an Opening Joint Session a good idea?  And, (5), What should happen if you or the mediator think that the other has a “blind spot” or just doesn’t get something?  The answers can vary widely from case to case!  Once the mediator knows your thinking on these subjects, he can prepare for the “people issues” as thoroughly as he can prepare for the legal and factual issues.  The mediation will be specially designed to meet your needs, and the needs of your client, in this particular case.   This kind of preparation will help get the mediation off on the right foot, and almost always lead to greater client satisfaction with the result, with the process, and with your performance as counsel.”

Mark Loeterman (www.mlmediation.com): “Information translates into power, both in litigation and at mediation. The careful use of information is an integral part of your bargaining strategy. At the outset, it is important to plan what information you need to obtain from, and provide to, the other side so the parties can have a meaningful negotiation. Lawyers are guarded about the information they reveal. They fear giving up some advantage or losing the opportunity to surprise an unsuspecting witness. Here are some practical steps for handling information most effectively. First, solve the information gap. Ask the other side questions that are designed to buttress your position or better evaluate risks. Next, consider offering discreet information which shows strength and confidence in your case, such as an analysis of damages or a case citation that supports a decisive legal principle. On the other hand, negotiators must understand how they can protect their most important and sensitive information. If you want to learn how to perfect these “blocking” skills, simply watch a politician being interviewed. Adroit politicians use a range of techniques to avoid answering even probing questions. Information is a valuable commodity. Thoughtfully timing and presenting select pieces can yield significant concessions from your adversary. The mediator can arrange an exchange of information that is orderly and reciprocal, and can clarify the positions being taken, assuring that no party feels vulnerable and manipulated by a one-way disclosure.”

Michelle A. Reinglass (www.reinglassadr.com): “Some parties have difficulty giving up their lawsuit. If asked, “Are you ready to settle and put it behind you?” they may answer “yes”, but their actions belie that. The plaintiff may have difficult letting go of the one thing that has kept him/her going-the chance to get redemption, or revenge. The defendant may not want to let go because of the fear of looking weak, or setting precedent (despite promises of strict confidentiality with “teeth” for a breach). Fortunately most cases do settle, but for those that can’t, I follow them until the “end”, which is too often predictable. So, how can a party going to mediation wean themselves away from the lawsuit? First is getting reality checks about the merit, value & risks of their position. For most that will require “processing” to reach that understanding. Second, is seeing the positive picture of their life without the lawsuit as a major part of it, draining (more like “sucking out”) their energy and good health. It helps to focus on their positive goals beyond “revenge”, giving themselves their own redemption, not relying on someone else such as a judge or jury, to give it to them, which will often be disappointing; or focusing on getting a job, or performing better in their personal and business lives, or putting their energy back into running their business without employees distracted by depositions , “gossip”, or their own fears. I have often said that litigation is negative energy. I enjoy mediating for the opportunity to bring people and businesses back into the positive energy of life, rather than the drain of a lawsuit.”

Jan Frankel Schau (www.schaumediation.com): “Be prepared to be flexible. You can’t map out your strategy until you know what or who is driving the conflict, what path will work best for an exchange of communication and until the necessary emotion and anger and disappointment is expressed–to somebody–even if indirectly to the other side of the dispute.”

Mike O’Callahan (www.mocadr.com): “My single best tip for a successful mediation is for counsel to budget and make time and properly prepare for a pre-mediation call with the mediator. The call is independent for each party involved in the litigation and lets them know you have read their brief and you can question specific areas without the posturing that some lawyers feel they must do in front of their clients. Too many times counsel submit their briefs less than 5 days before and throw something together at the last-minute or they send a 160 page brief the night before the mediation. Either way the brief is not very useful. An opportunity missed to educate the mediator by counsel. The mediator has to be proactive and make sure the parties know there is a deadline for the briefs to be submitted that will allow the mediator time to review before the pre-mediation call. The call can then be used to determine what, if any, settlement discussions have taken place and the potential range of exposure for the parties before they walk in the door for the mediation. Also, it allows the mediator to ask for supplemental information before the mediation and focus on common ground to form a global resolution at the mediation.”

Hon. Michael A. Latin (ret.) ([email protected]): “The mediation, though designed to bring the parties together, is still part of an adversarial process. Therefore, appear fully armed and loaded with all of your ammunition. Bring all of your critical reports, documents, deposition transcripts, and even a critical witness if necessary. Remember, that while you have been living with this case for a year or more, the mediator has very little concrete information when the mediation begins. Often, the two sides give completely opposite versions of the state of the evidence on the same issue. One side may be more truthful than the other or there may be information gaps that prevent one or more parties from making a fair evaluation of their case. If the mediator doesn’t have anything tangible in front of him or her to evaluate the relative strengths of the parties’ positions or representations, resolution becomes problematic – particularly where one side is either incorrect or misrepresenting facts. Give the mediator the tools to flush out those issues during the mediation by bringing everything you have in your possession that may refute misrepresented or contested facts. This includes documents and information that has not yet been turned over. Your opponent cannot evaluate those things about which he or she is unaware. I have had several cases that have settled because one side, which had information about which the opponent was unaware, decided to share the information at mediation. Appear with all your ammunition!”

Even though you tuned in to hear from experienced mediators, I’ll add my own three cents. First, I completely agree with the suggestions that counsel take advantage of the opportunity to have a meaningful pre-mediation call with the neutral. This can be HUGE. Second, if there is a way to create and communicate to the opposition the illusion that you are fully prepared to start trial tomorrow, this can create leverage. (Obviously this is not possible in a pre-suit mediation, and difficult if there’s no joint session.) Third, unless and until you really know and trust the mediator (or settlement conference judge/magistrate), I would resist requests to prematurely share your final, bottom line offer or demand. The neutral’s top priority is to reach a compromise, not to act in your client’s best interests (that’s your job); unless you know from experience you can trust his or her promise to keep your final number confidential, I wouldn’t risk sharing it.