In the early stages of a negotiation, typically, your goal is to gather as much information as possible about the other side, their needs, and what they likely hope to achieve in the negotiation. Much of this information you’ll acquire by asking questions. But as authors Pete Stark and Jane Flaherty point out in The Only Negotiating Guide You’ll Ever Need: 101 Ways to Win Every Time in Any Situation (Random House, 2003), not all questions are created equal, particularly when the negotiation table is involved.

Stark and Flaherty argue that the way you ask a question is just as important as the question’s content. Following are their eight key suggestions for structuring questions to maximize the information revealed about your negotiating counterpart’s needs and motivations:
  1. What’s your goal and plan?
    Your questions should be sequenced so as to lead to a conclusion you’ve plotted ahead of time. Based on what kind of information you’re seeking, you should know whether to take a direct approach or to disguise your intent. Closed-ended questions like, “Do you have the authority to make this decision in the current buying cycle?” will help with your sales forecast, whereas “Who else will have to be involved in making this decision?” should help reveal the other decision makers in the project. The bottom line is that you should know where you want to go with your questions, and then plan the questions to lead you there.

  2. Know thy counterpart
    Understanding the opposite side’s personality traits will help you determine negotiation strategy. Perhaps she’s a relationship builder who won’t feel comfortable getting down to brass tacks before establishing rapport by chatting about the weather or family matters. Or maybe he’s task oriented and will want to get right down to business. Try to determine your counterpart’s motivations, needs, values, and attitude toward time and you will be able to target your approach and questions more effectively.

  3. Start broadly, then narrow
    When sequencing your questions, begin with more “big picture” issues and then narrow your scope to go after very specific information. So, for example, a sequence might go as follows: “Did you keep maintenance records on your car?” “What did you record?” “How often did you change your oil?” “What kind of oil did you use?”

  4. Timing is everything
    People working their way through a delicious slice of chocolate mousse cake don’t want to be asked how their diet is going. Similarly, you need to pay attention to the appropriate time to ask potentially sensitive questions. Otherwise you risk derailing the negotiation process by causing your counterpart to take offense and clam up.

  5. Learn as you go
    Pay close attention to the responses you get, and then include that information in the follow-up questions you ask. Let the information you gather make your questions more targeted and specific, and use what you’ve learned to gain clarification on any issues you’re still unclear about.

  6. Ask before you ask
    Err on the side of politeness by asking permission to ask sensitive questions. Respondents rarely say ‘no,’ but they appreciate the gesture. Also, having granted you permission to ask, your counterpart will feel more inclined to answer honestly and in full.

  7. Shut up and listen
    For those who aren’t used to it, silence can be difficult to tolerate, particularly in the midst of a tense negotiation. Overcome your urge to fill the silence following a question with your own chatter. Give your counterpart all the time he or she needs to consider a response, and congratulate yourself on asking such a thought-provoking question.

  8. Make a note of it
    Unless you have a photographic memory, you’ll want some record of the negotiation in the form of notes. You don’t need to get down every word, but your notes should reflect the back and forth of the conversation, particularly the main points made by the other side. Taking notes also communicates how seriously you’re taking the proceedings and the weight you give to your counterpart’s perspective.
“A successful negotiator knows the wants, needs, and motivations of his counterpart and has a thorough knowledge of the topic of negotiation,” Stark and Flaherty add. “The easiest and quickest way to uncover the necessary information is through skillful questioning. With practice, you will find yourself asking better questions and gaining increasingly valuable information.”