Assume that both you and your client really want to settle. Really wanting to settle does not mean wanting to settle in the abstract or wanting to settle but only if you get complete capitulation from as well as public humiliation of the other side. It means that you and your client are prepared to make the necessary compromises to reach a resolution that both sides can accept.
In analyzing why settlement negotiations are not going well, first examine whether you are in fact the difficult lawyer. Your perception of the other side as being difficult and needing to be handled may be clouded by your own bias, ego, overinvolvement in the case, belief in the client's cause, or loss of perspective. ("We have seen the enemy and the enemy is us.")
Assuming you can honestly say that you are not the one preventing a settlement, the next step is to try to analyze the problem. It is helpful to examine why negotiations are not making progress. There are all kinds of reasons why settlement negotiations go badly:
Neither opposing party nor opposing counsel really wants to settle. Remember, really wanting to settle means being prepared to make the necessary compromises to get there, not merely being prepared to accept the other side's surrender. One clue: opposing counsel makes outrageous demands--demands so outrageous that you might as well take your best shot at trial because you could not possibly do any worse than what they are offering. Another clue: opposing counsel refuses to take your phone calls or respond to your written offers.
Perhaps opposing counsel says she wants to settle, but repeatedly files lengthy, frivolous motions. Or, the other side will not focus on the issues, but instead appears to be obsessed with your client's morally reprehensible behavior--your client walked out on her husband, had a baby with her paramour, took the paramour to Barbados on the husband's American Express Card, and is therefore morally bankrupt and has no right to half the equity in the marital home. This kind of attitude is a hint that these people are not quite ready to deal with the real issues and maybe never will be.
Opposing counsel wants to settle but the opposing party does not. Some people simply do not know how to compromise. It is not in their nature. Giving up something seems like surrender. Often such people tend to see everything in moral absolutes--"He done me wrong, so he has to pay." Anything the other side gets is seen as a reward for wrongdoing. Often such people are genuinely unable to see any other point of view but their own. Settling a case with someone like that on the other side is extremely difficult, and sometimes impossible.
Some people have a need--albeit misguided--to have their drama played out in a courtroom. They believe what they see on TV. They think they are not only going to win but also will be vindicated publicly, given a verbal pat on the back by the judge, and told they are the victim of a great wrong perpetrated by the other party. People like this cannot settle. And when they do give into pressure to settle, they invariably try to renege before the ink is dry on the deal.
In other words, sometimes it may seem as though you are dealing with a difficult lawyer when in reality the opposing counsel has a very difficult client he or she cannot control.
The opposing party may want to settle but opposing counsel does not. Again, there are clues that this may be the case. For example, your written offers are apparently not being communicated to the other party, you cannot get any feedback from opposing counsel about your offer, or opposing counsel won't return your phone calls. Perhaps opposing counsel makes totally absurd and outrageous demands. The clues can sometimes be ambiguous; they may be the result of the party's unreasonableness, the other lawyer's unreasonableness, or both.
Opposing party and counsel want to settle but there is something standing in the way. It may be that opposing counsel is unskilled in the techniques of good negotiation. Perhaps he does not understand that most of the time you need a win-win result. Or, she will not put her cards on the table and tell you what she wants; for example, she says her client wants alimony but will not say how much or for how long.
A variation on this theme is the opposing counsel who attempts to get you to bid against yourself--"Your offer stinks, try again"--or will not commit her client to a firm counteroffer--"We can't accept your offer to settle for 'X,' but I am prepared to recommend to my client that she settle for '2X.' Will your client accept '2X'?" This is not an offer. It is a request for another offer from your side. It's a slightly more polite way of saying, "Your offer stinks; try again."
It may be that opposing counsel is ignorant of important legal issues that must be understood to reach a resolution--for example, there are tax consequences flowing from the deal and the opposing lawyer does not understand them. Sometimes opposing counsel is misinformed about the facts or has not done his homework. He may not have gotten out a calculator or used a spreadsheet to actually calculate the result mathematically and may not understand what their offer really means to your client. He may not even understand what it means to his own client. Therefore, he may not understand that the deal they are proposing cannot possibly work.
There is also the opposing counsel who is either lazy or overloaded and therefore waits until the last possible moment to get serious about talking settlement. Quite often this person is also ignorant of relevant law or essential facts, thus compounding your problem.
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