Questions are keys that unlock new doors of connection and discovery. 

I have been fascinated with questions for many years, both the internal questions we use to make decisions and the questions we ask others. Whether you are being interviewed for jobs, meeting clients for work, or just spending time with friends, a thoughtful question can move both sides toward a trusting relationship and concrete action.

Author Stuart Firestein wrote, “One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt changes in entrenched thinking. Answers, on the other hand, often end the process.” To live this type of generative, exploratory life, building a habit of asking questions is an important first step.

So how can we practice asking better questions in conversations? A genuine interest in the other person is key, but it doesn’t hurt to have a few questions up your sleeve. Here are a few of my favorites.

  1. What are a few moments in your life have you felt most alive?
  2. What is one way you want to grow over the next few months?
  3. Who in your life do you most admire? Why?
  4. Do you consider yourself a creative person? How do you express your creativity?
  5. What little things have brought you joy recently?
  6. What is a new skill you want to learn or topic that you want to study?
  7. What advice would you give to your (insert age 5 or 10 years younger)-year-old self?
  8. What does an ideal Saturday look like to you? What about an ideal work/school day?
  9. If you had to start a company or organization of some type, what would you start?
  10. What are some childhood moments that you remember clearly? What childhood events helped shape you into the person you are today?

These questions offer entryways to conversation, but no specific question is as powerful as a deep curiosity and excitement about the life of whoever you find in front of you.

As I approach the 60th episode of my Voices of Santa Clara podcast, I’ve realized that the best stories and insights often come from asking follow-up questions when a guest hints at a meaningful time in their life. What did you learn from that experience? How did that experience make you think differently moving forward? Why did you pursue that path? The greatest questions aren’t found on the list above, they come when you fully listen and ask about an insight the other person raises.  

This type of conversation can help build stronger friendships, and start a mutually beneficial learning process. The asker learns about the other person, and the answerer can reflect and clarify their growth process and values. One hallmark of a great conversation is when someone hears themselves saying something they feel or believe, but have never clearly articulated before.

Which of your relationships could benefit from this type of questioning? What question have you been meaning to ask someone? What would you add to this list?