Negotiations: Asking the Right Questions in the Right Way

As I was negotiating a deal for two parties that had the potential to create a real win-win for both, I found myself continuously irritated by the person on the other side of the table.  I realized it stemmed from the way they were asking questions.  The tone was disdainful, disrespectful and demanding. The questions themselves didn’t seek useful information to help us expand the opportunity but were mostly just statements disguised as a question.  As you can imagine, this didn’t put me in a very collaborative, “win-win” mood. 


The types of questions asked and the tone of voice when asking them can have a major impact on any negotiation, including derailing it completely.  Use of the wrong types of questions or an antagonistic tone immediately turns the negotiation into a competition where each side will try to beat the other – missing the opportunity to expand value for everyone.


Here are my rules for asking question in negotiations:


  • Ask questions designed to get to the “why” behind their positions and statements.  Their answers will help you determine what is really important to them.  You can then fashion proposals that meet their and your most important needs.

  • Ask open-ended questions that get them to talk as much as possible.  Information is power.  The more you know, the more leverage you have.

  • Ask clarifying questions.  We all understand words differently.  Instead of making assumptions about meaning, ask more questions.

  • Ask focused questions only when you are ready to get to the details, but not too early in the negotiation.

  • Avoid closed-ended questions that can only be answered with a yes or no. If you ask: “Is that the best you can do?” and they answer yes – where do you go from there?


There are some questions you should always ask.  These questions will give you the information you need to craft a deal that gets you the best possible outcome.


  • What do you hope to achieve (as a business with us, today)?  This will help you determine what is important to them.

  • What are your company’s (department’s) goals, strategy and vision? This will help you determine their most important needs.

  • “Tell me more about that” – “Help me understand” – this will open up the dialogue and build trust to collaborate on great solutions.

  • What can I (our company) do to get . . . (whatever it is you are seeking)?  Most will tell you what you have to do – you have to decide if you are willing.

  • Does (my competitor) get a better deal?  How do I get that deal?  Again – more information to find a better solution.

  • How do I better our deal?  Once you have an agreement, this is a safe way to explore further value creating opportunities.


Great questions in the right tone can open up all kinds of possibilities and allow you to find solutions in negotiation that create the type of win-win solutions we all seek. 

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