Remember when you were a kid and your mom forced you to ask a group of the “cool kids” to play?

Close your eyes… you remember. As you walked toward the cool kids, your mouth felt dry. Your palms got sweaty. Your heart felt like it was going to burst from your chest and your breath came in short gulps. You approached the kids and finally gathered the courage to ask in an awkward croak, “Can I play?” Before the kids responded, you stole a look at your mom who was beaming with pride. But you were terrified. Doesn’t she know your fears? Doesn’t she appreciate what could happen? What if they laughed at you? What if they made you feel stupid? What if they said “no?”

Believe it or not, this fear of being told no, of being laughed at and of feeling stupid, follows most people into ripe old age. We crave the attention of others. We want their approval. We need fellow humans to be supportive, encouraging, and kind. We need this at home, with our friends, and yes, even with our business associates.

But here’s the rub: the world doesn’t coddle us. Businesses don’t support employees by offering hugs and “boo-boo bunny ice” when we get our licks. It’s a dog-eat-dog world out there and we’ve got to find a way to navigate through it.

In the mediation context, the worst thing someone can say is NOT “no.” Rather, “no” gives us information we previously lacked. It tells us where the other parties stand on certain issues. It sets parameters for settlement. It lets us know how seriously the other parties are taking their positions and why.

Instead, the absolute worst thing we can hear in a mediation is, “why haven’t you asked before?” An answer like this leads to all kinds of potential “what if’s?” What if you had asked before? Could litigation have been avoided? Could the issues have been resolved amicably before the filing of a lawsuit, saving considerable time, money and emotional distress? That depends. It depends on the skill of the questioner to get to the heart of the problem, it depends upon the answers given, and it often depends upon the timing of the question itself.

Questions that might be asked at the outset of a conflict in an effort to resolve a dispute will be drastically different from those asked on the eve of a trial. For example, an employee complaining about sexual harassment to a human resources director might be satisfied with the company’s actions in response to the alleged harassment if all of his or her concerns are addressed. But never assume you know what all of those concerns are. Ask questions that get to the person’s underlying interests, not just their subjective complaint. Perhaps firing the offender seems like the right choice, when in reality there’s a continuing culture of harassment at the company. The employee is not likely to be satisfied if you cut out one tumor only to leave the cancer. In an early stage of conflict, the questions asked should be broad enough to facilitate dialogue between the parties involving candor and creativity in an effort to communicate freely and without fear. A mediator facilitating these types of difficult pre-litigation dialogues can help craft solutions that will benefit all parties while minimizing potential human and financial costs.

Questions that might be asked during litigation are often by necessity defined by the more narrow parameters of relief, monetary or declaratory, simply because these are the only remedies available in court. And once insurance companies get involved, often the only thing to discuss is money. But there are two elements to the idea that the “worst they can say is no” which must be considered. What is it that you are asking and what is the timing?

There are strategic reasons in pre-trial mediation to not have the attitude of “the worst they can say is no.” For example, coming into a mediation with a demand that is hundreds of thousands of dollars over a previous settlement position with no explanation for the defense is a great way to immediately chill negotiations and prevent settlement. On the other hand, some questions can shape the other party’s perceptions about what exactly is in dispute and how the opposing party is going to characterize certain facts. Perceptions can inform the entire settlement process from start to finish, good or bad. Wouldn’t you rather ask the questions that can do the shaping?

One recent example comes from a personal injury case where the plaintiff’s lawyer lacked client control. The plaintiff had a list of prior medical conditions that the defense counsel and adjuster asked me not to disclose because they felt it was a “smoking gun” for their case. However, the plaintiff’s attorney did his research and knew about these prior medical conditions. He took the time to address his concerns with his client, and then asked me to disclose these prior medical conditions with the defense and to specifically question the defense about how this disclosure was going to affect settlement negotiations. I communicated their responses to the plaintiff’s attorney who then used that information to help adjust his client’s expectations and ultimately his negotiating strategy. He understood that asking the question would get him enough solid information in front of his client to help educate the client about the perils of moving forward so aggressively, but it also gave the plaintiff’s attorney something he didn’t expect… an opening. The defense told plaintiff’s attorney they weren’t offering more than one-third of the medical bills on a non-disputed liability case because of the prior medical conditions. But they also said that if the plaintiff could prove that something didn’t exist prior to the injury, they would put more money on it. Like I said, the plaintiff’s attorney had done his research and was able to prove one of the injuries. The defense did put money on it and the case settled. The questions informed each party of expectations and needs. And instead of hearing a “no” to an outrageous demand not based in reality, the lawyer heard an opening. Both sides walked away happy.

Most conflict is born from either miscommunication or an abject failure to communicate. Even in late stage settlement negotiations, communication between the parties is key to resolution. What is communication but a series of questions and answers? The last thing you want to hear after spending considerable time and money on a conflict is “why haven’t you asked before?” Failure to ask questions, even hard ones that might result in negative answers, is a failure to communicate.

Please feel free to call or e-mail me with your questions. I look forward to helping you resolve your dispute.

By Terri Lubaroff

Terri Lubaroff, Esq. is a conflict resolution specialist, having honed her skills first as a film and television producer and later as a full-time mediator and arbitrator. She specializes in Entertainment, New Media, Employment, Consumer Torts and Business Disputes, and is adept at dealing with difficult personalities. She is a member of the Florida Bar and is a full-time neutral in Southern California with Agency for Dispute Resolution.