That's also the best way to learn.
In law school, we're taught the opposite. The professors may pretend to ask questions, but essentially they're orating. Law students learn that lawyers are supposed to be orators. And not particularly nice ones.
Mediators spend a lot of time dancing around trying to figure this stuff out because parties protect this information like deep, dark secrets. I'm sure that more than one mediator has considered waterboarding to find out what the heck someone really wants. But there's a much simpler way.
The most powerful tool a mediator has is the question, “Why?” Typically, in a joint session or even an initial private breakout, parties will give the mediator chapter and verse of the strengths of their case. If the case is really that fantastic, a mediator may well wonder, why are they here?
Get the parties alone. Start by asking, “Do you want to settle this case?” In voluntary mediation, the answer is always yes. We know that everyone wants to settle, sometime; we need the parties to acknowledge that as a goal. Then simply ask, why.
Why do you want to settle?
The answer will usually surprise you. When directly asked the most obvious question possible, advocates usually answer directly. They will tell you problems and weaknesses in their case that you might never have guessed. They will tell you problems they wouldn't admit if you tried to beat it out of them.
If anything they say sounds vague or still strangely guarded, just ask again: why is that a problem? Why are you concerned about that? Why does that make you want to settle? Because if there are no problems and there are no issues, you obviously wouldn't be here. And you're the first lawyer in history to have a perfect case.
Asking why is a good strategy later on in the mediation, too. When one party is wedded to a position that doesn't seem to make sense, asking why will help you learn what's really on their mind. It will help you understand how they see the problem and give you ideas about how to solve it. Asking why a party is making a particular demand or offer helps everyone think things through. Throughout the mediation, at any impasse, asking why will help you understand more fully what the parties are really saying they need.
As long as you are truly asking to learn and not as a sort of argument or test, asking open questions—especially why—is a great method.
Trial lawyers are accustomed to ruses, gambits and stratagems. You will never learn as much as when you start with an open, direct question and listen carefully to the answer.
A mediator's job is to help the lawyers get what they really want. Even though they may do everything they can to keep us from finding out the flaws in their case, and what they really want, ultimately the parties really do want us to know. The best way to find out is to ask, simply, why?