Seven reasons your case will fail to settle

How to work with your client and your adversary to avoid the seven pitfalls of litigation that will doom settlement talks and force you to trial

Ian Paul Zimmerman
2022 September

After 42 years of trying cases – both criminal cases in my earlier years as a public defender in NYC and civil cases running the gamut from PI to divorce to real estate, I’ve learned a lesson or two – actually seven that I’d like to share.

The seven reasons cases fail to settle:

There is excessive acrimony and bitterness between the lawyers;

One or both lawyers has insufficient control over their client;

The parties themselves are unrealistic in their expectations;

There has been inadequate discovery on one or both sides, causing uncertainty and untested assumptions;

One or both attorneys is gambling and only secondarily treating the case as fact driven as opposed to wish driven;

The parties have had little or no opportunity to communicate their more realistic positions;

Too little assistance from an impartial neutral or settlement judge.

Nearly every case that I fought at trial – whether for a plaintiff or defendant – had one or more of the above seven deadly sins as its driver. Let’s take a closer look.

Excessive acrimony

Litigation is often nasty in addition to being contentious. Litigators take a perverse pride in being warriors and a certain glee in a take-no-prisoners approach. The problem of course is that once you begin or get sucked into this fiery battle, it’s like Sherman on his march to Atlanta; it’s hard or impossible to stop and you want to see the other side burn.

Putting the brakes on is not easy. When you’ve been harassed for two years by your opponent “just say no” doesn’t work. Often, there’s been too much carnage. Enter the mediator, who hasn’t spent the last two or more years pissing in your coffee and doing everything to make your life and especially your weekends miserable. (How many late-Friday letters and filings I’ve authored and received shall go unaddressed).

But there is a time for all things under heaven, including peace and hopefully, a moment of clarity when you ask yourself if you’re prepared to die for some lady who tripped outside a Walmart even if she’s had two laminectomies?

Will that battle make the world a better place?

Unsolicited advice: Save your blood and spittle. It isn’t worth it nor are the cardiac stents you’re heading for. As a court clerk once said to me nearly 40 years ago, “Do you think the world will care if another lawyer dies of a heart attack?

Insufficient client control

Client control can be precarious. You want and need to show the client how hard you are prepared to push, and yet at the same time, need to rein in the client who’s unrealistic. You find yourself having to talk out of both sides of your mouth (a relatively easy skill that we readily mastered) but still some clients are simply too pig-headed, refusing to listen no matter how experienced you are or august your reputation.

Solution: If you’re having trouble controlling the client, let the mediator do your “dirty” work. I’ve found that the most recalcitrant clients will eventually listen provided you listen to them first. We all believe we’re good listeners, primarily because we don’t have any physical hearing deficits or wax in our ears. That’s small comfort. To really listen is to make every effort to enter the world view of the speaker no matter how irrational it may initially appear. Consider: In their world they are making perfect sense. It’s hard to accept but you really must enter the world of the speaker where one and one equals three. Once inside, you get to play with the numbers, but you have to get inside first, knocking very gently on their door. Even the most obdurate client has a logic that supports their position. Good listeners use the speaker’s logic and not their own. It’s magic and recent discoveries in the field of neurolinguistics bear this out, i.e., “People are always making sense,” it’s just not your sense nor even our shared “common” sense. So what? Respect the speaker’s internal “logic” no matter how bizarre, and discover how they get to three adding one and one together, and you get the keys to the kingdom, or more modestly, a place of “deep rapport,” where you have a chance to then lead them out of their cave. You might think this a bunch of hooey and poppycock but you’d be wrong (except inside your own brain where you’d be right).

Unrealistic expectations

Most litigators are not realistic in their assessment about the relative strengths and weaknesses of their cases. It comes with the territory. Old-school judges act imperiously, chiding you about the value of a case you’ve worked up and lived with for years and then tell you to send in opposing counsel for the same treatment. You know the whip-saw drill. In contrast, a skillful mediator needn’t hammer the parties, but can help illuminate the more vulnerable aspects of the competing claims without having to resort to haranguing you or your client. Use the mediator for information that has heretofore been hidden from your eyes because your sword and shield have been held too high. The mediator’s comments aren’t offered to “beat you down,” but rather to raise up your knowledge base so you don’t have to learn for the first time at trial. There is an expression amongst seasoned pilots: It’s better to discover your plane’s problems while it’s still on the ground. Got it? Now proceed to runway 30 and hold short.

Inadequate discovery/untested assumptions

Where discovery is incomplete, speculation grows. Nature abhors a vacuum. Many (too many) cases fail to settle because the parties have not adequately turned over the rocks they need to look under. A skillful mediator can assist here. Often, parties glean new information about their case in the mediation itself, although this isn’t a great substitute for doing your homework before the mediation. Some less-than-forthright attorneys (with little or no real intention of settling) agree to mediation for exactly this reason – to suss out your case and take your pulse. The frustrating fact remains that where there has been insufficient discovery, there is simply too much left unanswered, or as Donald Rumsfeld said, too many “unknown unknowns.” Remember well this ditty: “A confused mind says no.” Make sure you don’t have too many unchecked boxes. They only invite speculation and chest-thumping bravado.

Similarly, nearly every litigator overestimates the persuasive efficacy of their experts, minimizing or ignoring the eventual chinks in their armor following a blistering cross-examination. Consider: They might have impressed you, but how is it going to play in Peoria?


Some attorneys are not only warriors, but gamblers too, substituting “wishing for the big hit” for cold facts. Most experienced mediators will spot and attempt to disabuse the poker-playing advocate, reminding him or her to leave that at the craps tables. Still, the possibility of “hitting it big” often clouds more rational thought. Don’t let it cloud yours. What happens in Vegas stays there; resist the temptation to infuse your case with a jackpot mentality. Buy a lottery ticket if you must.

Little opportunity to communicate/ more assistance needed

Finally, too often parties have not had enough time to simply talk, listen and adjust. Cases are kinetic (to borrow from contemporary military jargon) and facts change on the ground. A witness goes south on you, a document or recording surfaces that isn’t pretty, a ruling goes against you, etc. Cases move and morph. Parties need time to weigh the scales again and again as the case moves and changes. Lawyers stuck in yesterday’s facts do poorly. Read Eric Hoffer’s “The True Believer” and make a promise to yourself that you will never be a zealot (at least while representing a client). You’ll do much better.

Negotiation takes time and there’s no way around it. No one wants to make big jumps too hastily. No one wants to leave money on the table. Often, there hasn’t been enough time to allow the posturing to mature into more realistic positions. Like a pregnancy, negotiation can’t be rushed. It takes the time it takes. There is a recognizable and predictable sequence to every negotiation. There are steps. It is an organic process. Parties need the time to allow the process to unfold. Every negotiation begins with a discussion of the facts and then switches to money. Back to more facts and then back to money. Usually, by the end of the day there aren’t many facts left and the process turns to money demanded and offered. Back and forth. Over and over. A skillful mediator needs to make sure each side has had enough time to do their level best to engage in this process, allowing each side to get as close as possible to their respective breaking off point before the pens can come out and the matter is settled. For me, the most successful mediations are those where both parties got as close as possible to walking away, yet finally signed. It’s more than leaving “each side dissatisfied” as we so often hear as a salve to an unpleasant and frustrating settlement. It’s allowing the parties themselves to go as far as they possibly can go before inking the deal.

If you and your adversary are successful in avoiding the seven pitfalls above, your case will very likely settle fairly and settle successfully. Alternatively, you can fight it out, die on some unnamed hill and leave your share of the practice to a partner who doesn’t deserve it.

Ian Paul Zimmerman Ian Paul Zimmerman

Ian Paul Zimmerman is a mediator practicing throughout California after a litigation and trial practice lasting 42 years, with four cardiac stents as unwelcomed trophies. He is admitted in both New York and the State of California. Ian formally hosted “LawTalk,” a call-in radio show in San Francisco focusing on contemporary legal matters. He has testified before the California State Senate and has appeared on numerous national TV shows including Larry King Live. Email:

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