Five Questions for Intentional Conversations

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I believe we are all capable of having smart, meaningful, and honest conversations. We can go beyond small talk and repeated conversations of “Hey, how are you?” and “Good!” 

How can we get past that point and move into intentional conversations? The following five questions can help start us on our way. They are questions we should also be willing to answer as we model vulnerability and make the other person more comfortable in sharing. It’s a conversation and not an interview!  


1. What’s your story?

This open-ended question gives the speaker more control in what to share. They can give their whole life story. They might share something else, like where they came from, how they chose their college or about their career. Even better, the question creates more things to follow up and continue the conversation!


2. What would you do if you knew you couldn’t fail?

This fun question gives insight into the person’s dreams and aspirations. It also is a bit more vulnerable because it shows where they fear failure. Be sensitive to their dreams and be open to sharing your own aspirations!


3. What is your favorite quality about yourself?

Their answer to this question provides a perspective on how they view themselves in a     positive way. It also gives us the opportunity to affirm them and share what we like best about them! 


4. Tell me a favorite memory/story.

Memories and stories are great ways to connect with each other. We can reminisce about shared memories if we have known each other for a while. Or, we can learn about a new friend’s background and what moments they value. Maybe they had a great kayaking trip as a kid, or they recently threw a surprise birthday party for their best friend. We’ll never know unless we ask.


5. What has God been teaching you lately?

This question is best suited for Christians since it directly references God, but it can be     adjusted to be a starting point about God if the question is adjusted to “what have you been learning about in life lately?” Both versions leave room for a wide range of answers. They could share about a topic brought up in a church sermon or a Bible study, or go in-depth with recent struggles or praises. With the alternate version, we can share about how God has been teaching us and introduce faith into the conversation. We can listen to what our friend has been experiencing and speak truth into how God is at work in their lives.  


I hope these questions are helpful as we have conversations with others. The best questions are asked honestly and the answers are listened to with genuine interest. We should get in the habit of asking good questions and listening well. Now, let’s go schedule those coffee dates with that new neighbor or go call that friend we’ve been meaning to catch up with. It’s time to be open, ask questions, and have intentional conversations again. 

Let’s keep this conversation going! Do you have any questions you’d add to the list? Please share in the comments. 

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