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Eyes-to-the-Sky Questions

I recently read the book Just Listen, by Mark Goulston, which introduced me to the concept of “eyes-to-the-sky” questions — the kind of questions that usually cause people to pause, look up a moment, and consider something in the bigger picture. These kinds of questions tend to change and deepen the connection between the people in the conversation because they invite a person to share a little bit about their personal thoughts, feelings, and experiences rather than giving a short “yes” or “no” or “fine” or “good” that may end the conversation. They communicate to the other person that you care about who they are, what they are experiencing, and what they have to say. These questions often include words like most, least, best, worst, etc. to encourage reflection, although they don’t have to.

Here are a few examples: What’s the best part of your work right now? What’s most exciting to you at the moment? Who do you most admire? What do you most want people to know about [fill in the blank with whatever that person loves, cares about, or is experiencing at the moment]?

I’ve been using these questions in many of my conversations lately and am amazed at how much I’ve learned about people and how much more we’ve connected in part because I have changed the way I worded my questions.

Goulston’s book contains many other tools for making conversations more productive and valuable and for connecting with people who may seem otherwise unreachable. They’ve been very helpful to me so far, and perhaps they will be helpful to you as well. For a link to this book and other helpful reads, visit

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