​Deep conversations are rare in a culture plagued by living in the shallows, focused on the new and urgent, and enslaved by hurry.

Focus on these four elements to grow in the skill of deep conversations.

Be curious. Slow down. Take some time, even a moment, to ask yourself what you can ask someone. Pause. Take a breath. Reflect on what you want to learn, what you are confused about, a decision or life transition you'd like to know about, or a particular idea or topic you want to explore. Be curious about yourself and the reactions you have to the person and to the conversation. Listen from the inside out by first being curious about yourself. Be mindful that you have assumptions. Allow them to be challenged.

Be present. Allow for silence. Focus all your attention on listening. Be open to whatever they have to say. Don’t try to assume you know what they are going to say. Be open-minded and be willing to be surprised. Listen to the entire message of what is said. Pay attention to what is not said. Be aware of your body language, tone of voice, and what that might be communicating.

Be genuine. To have a rich and deep conversation, it's crucial to be open and share what you think. But you don't need to be in a hurry to share what you think. Be quick to listen and thoughtful and genuine in your response. Live out of a sense of belonging, not shame or fear of what others think of you. When you do speak, be clear. Do not hide what you believe out of fear or let selfishness inform what you say.

Ask questions. To start or deepen a conversation, ask open-ended questions. These questions typically begin with the words How, What, or Why.

Ask questions to explore: "Could you tell me more about [topic/idea]?", "What stood out to you from...?"

Ask questions about their experience: "What was it like to...?", "What led up to...?", "What did you learn from...?", "What was surprising about ...?".

Ask questions to challenge: "What was most difficult about...?", "How did you struggle with ...?", "What is missing...?", "What was behind ...?". Asking 'what was behind' a particular decision is a way to ask why and sometimes helps people think more concretely than simply asking why.

If you want to move beyond the surface, ask people questions. If you want to go deeper still, ask follow-up questions. Sometimes people only know what they think if asked and carefully listened to. Look for what follow-up questions you can ask in a conversation and how you can go deeper.

One of the greatest gifts you can give people is loving attention while having a thoughtful conversation. Never underestimate the power of a caring conversation rich with curious questions.

These are simple reminders, and you know them. But do you practice them? Choose one of these four skills and intentionally practice this week.


"Authentic is such a worn-out adjective; it can feel meaningless. I suppose therefore I prefer grammatically challenged phrases such as "broken-open-hearted warriors." The action that creates true authenticity is embedded in that adjectival phrase. But the call is to authenticity. The call is to be real; to show up mad, scared, fearless, or joyful—or all the above. "

Jerry Colonna, Reboot

"Truly creative people in all fields can temporarily suspend their ego and simply experience what they are seeing, without the need to assert a judgment, for as long as possible. They are more than ready to find their most cherished opinions contradicted by reality. This ability to endure and even embrace mysteries and uncertainties is what Keats called negative capability."

Robert Greene, Mastery


What pain breaks your heart? What people do you fear? Serve them.

Do not stop at mere outrage over injustice. How can you love someone today?

What practice or habit can you commit to this year to serve others?

What is your purpose? Who are you serving?


The only thing between you and a deeper conversation is asking a curious question.

Live wisely,


Do you want to cultivate more of the good, true, courageous, and beautiful in your life?

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