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The Art of Asking Questions

By: David Hoffman, IAM Distinguished Fellow 

Email:dhoffman@bostonlawcollaborative.com      Posted:  July 30, 2015

Mediation is sometimes referred to as “the art of asking questions.” One of my mediation teachers, David Matz, described this process as similar to fishing – we cast our questions on the waters of the conflict, and sometimes we catch a fish (i.e., a really useful answer)!

Our goal in asking questions is to understand people’s stories, discern their underlying interests, and explore the feasibility of various settlement options. Curiosity is an essential trait for mediators.

For negotiators, asking questions is equally important, even when there is no mediator present. The best negotiators ask lots of questions – and here are two stories that illustrate the point:

First Story: Many years ago, I served as a negotiation teacher for the first-year associates at my old law firm, Hill & Barlow. Each year, I gave the associates the same negotiation exercise – a case called “Sally Soprano,” one of the most popular negotiation exercises published by the Program on Negotiation at Harvard Law School. It’s a scorable exercise in which the parties are negotiating a contract for the services of an opera singer. After the exercise is over, the associates and I calculated who got the best and worst deals for the opera singer, and explored the reasons why.

One of the most important parts of this exercise was the next step, in which I invited two senior partners who had never seen the “Sally Soprano” exercise to do the negotiation in front of the associates. Each year I got to see good negotiators, but the very best result ever was by a senior partner named Charles Dougherty, who got an exceptionally favorable outcome for the opera singer in a rather surprising way. He did not pound the table, make excessive demands, or berate the other side for their stinginess. Instead, he calmly asked a series of questions about the opera company and its interests and concerns. He asked what the opera company had paid other performers and what their projected finances were for this particular opera. He asked about their alternatives to an agreement with his client, Sally Soprano. 


Notably, Charles asked the questions in a non-threatening, thoroughly engaging way. He exuded an air of curiosity, compassion, and helpfulness – “it appears that all of our interests would be served well by making a deal here,” he said. By the time he got answers to all his questions, he was able to offer a deal that met all of the opera company’s needs and interests and maximized the value of the contract for his client. And, just as important, his client and the opera company left the table with positive feelings about this new contract. Charles did a superb job, and he made it look easy!

Second Story: My late wife, Beth Andrews, applied many years ago for her first job as a clinical social worker with an advertised pay range of $40,000 - $45,000. The agency offered Beth the job and proposed paying her $40,000. Beth asked if she could think about it, and then asked me how she should negotiate her salary. She was nervous about appearing greedy – she thought that would be a poor way to start a new job. She also worried that if she was too tough a bargainer, the agency would withdraw its offer. So I proposed that we rehearse the negotiation.

I suggested that she begin by asking whether the agency was willing to pay more than $40,000. Beth then asked me what she should say if they came back with an offer of $42,500. I said, “What would you like to say?” “I think I would just say ‘Yes’!” she said. I suggested the following: “What if you then asked them what they would be looking for in someone that they paid $45,000?” Beth said, “I think I could do that.”

The next day Beth spoke on the phone with the agency representative, and in response to her first question they increased their salary offer from $40,000 to $42,500. “Do we have a deal?” the interviewer asked. Beth, summoning her courage, asked, “What would you be looking for in someone that you paid $45,000 a year?” The phone line went silent for a few moments, which seemed like a few minutes to Beth. Then the interviewer said, “You are a really good negotiator – we can offer you the full $45,000 per year.” Needless to say, Beth was elated, accepted the offer with gratitude, and had a very positive feeling about the job throughout her tenure.

The Takeaway: Curiosity can be disarming – in part, because it is so unusual in negotiations. But the art of asking questions has more than mere economic and instrumental value. It also has value in forging relationships. This is especially important if the negotiation involves a contract or other ongoing connection. And, being relational has intrinsic value for both parties. (For an excellent discussion of this last point, see the forthcoming book by Louise Phipps Senft and William Senft entitled, Being Relational: The Seven Ways to Quality Interaction and Lasting Change.)

Studies of team performance in business have shown that the highest performing teams have communication styles in which the ratio of inquiries to assertions is high. Similar results have been seen in studies of married couples.

So, in your next negotiation – whether it is in a conference room or at the dinner table – consider: should the next words out of your mouth be punctuated with a period or a question mark?


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