The Power of Asking Questions: Unlocking Better Negotiations and Deeper Connections

Egyptian writer Naguib Mahfouz said, “You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.” Questions are a pillar of communication. They can help you appreciate a different perspective, collect information that enhances your understanding, or even find out something that surprises you.

To be a great negotiator, you have to be a great listener. Some may believe you should come to the table armed with all the information you need, with little room for curiosity. One of the tenets of my teaching is that, while you should do your research and always be prepared, you should never be so overconfident that you don't leave room for reflection and learning.

There’s also a misconception that, when bargaining, all questions must be related to the transaction at hand. I find value in asking non-transactional questions as simple as “How are you feeling today?” and showing genuine interest in the response. Making an effort to ask meaningful questions about who you’re negotiating with shows your empathy and investment in the conversation.

This type of personal information may seem inconsequential. In practice, asking people about themselves can diffuse tension and make everyone at the table more comfortable. You have the opportunity to find common ground before the negotiation even starts. This goes beyond curiosity—it’s really about caring. Poet Henry David Thoreau said, “The greatest compliment that was ever paid me was when someone asked me what I thought, and attended to my answer.”

Asking questions can also help you understand your counterpart's needs, wants, and motivations. You could even discover the areas in which they may be willing to compromise. The information you collect could help you negotiate better.

This investment of your time and attention makes you far more persuasive in the delivery of your ask. You might realize how you can present your offer in a way they’re more likely to respond to, whether this means softening your approach or coming on strong. You’ll benefit from taking the time to get to know them and by gaining a deeper understanding of who they are.

There’s an important message behind the simple act of asking questions, one that more people need to hear. When you ask questions and truly care about the answers, you acknowledge your own uncertainty while humbly revealing you don’t know everything. You show you’re willing to put in the effort to understand all sides—a powerful message to send in today’s world. 

Have a conversation rather than an interrogation. Use your emotional intelligence to read the room. Lean into your humanity and be present. Let them ask you questions in return.