#20: A Sure Fire Way to Great Conversations over Dinner [podcast/video]


When I heard the knock on the door, I must admit I was nervous again. I don’t know why I still get nervous–we have done this many times before. I realize there is a fear of mocked for being weirdly intentional.

As the large family came in, we hung up their coats and gave them a drink right away. Thankfully, the food prep timing had worked out and it was all hot and ready.

This time we were adding two elements to our “get to know you dinner” with friends.  Telling them WHY we had invited them, and ASKING them thoughtful questions.


The first–to gather everyone together and explain why we are getting together and what we appreciate about them. I was as nervous as a cat on a hot tin roof. My family said it went great, but I felt like a fool saying, “We appreciate you for this and that.”  And secondly–I introduced two questions for dinner-time discussion, “. . .because we want to get to know you better.”

Do you know how odd it feels to say out loud to friends, “I want to get to know you better”?

Here is the cool conclusion to the story: Dinner conversation was fun, engaging and meaningful. They shared more deeply than I would have imagined.


How did two questions on a piece paper draw this out? Keep reading to learn more. You will also find a video that tells how to create and implement good questions.


Here is the video



Why Ask Good Questions?:

  • Deeper: Every time we have asked 2 good questions, we learn something meaningful.
  • Known: People are yearning to be known. The problem is that there are few intentional places to be known. Good questions scream, “I want to know you better.”
  • Safe Place: When we go to someone’s home we often wonder what the customs of the home are. Good questions create a safe place to know what is expected.
  • Fun: Our experience is that dinners with no questions can ramble. Dinners with good questions launch into really funny stories. We laugh more with 2 Question dinners.


How to do Good Questions:

  • Relax: You relax. So, others can relax.
  • Gather: Before you sit down, gather everyone together. Tell them how you appreciate them. Then explain that there are two questions for discussion tonight because you want to get to know them better.
  • One Conversation: Set the expectation of one conversation. A divided table = poor conversations.
  • Listen: Others want to be heard. Listen longer than is comfortable.
  • Don’t One-Up: Don’t try to identify or one-up their story. Instead, ask a follow-up question about their story.
  • Follow-up Question: Ask something about what they just shared. It shows you care.  You will get something deeper.
  • Draw Out: Tell the quiet person you want to hear what they have. Ask twice, but not a third time.  In other words, don’t force them to share.
  • Size: The ideal size around a table is 6 to 8 people. 10 is a stretch. 12 is pandemonium.
  • Start: Push to have someone else answer first.
  • Laugh: Laugh often, soon, and with gusto, to relax everyone.



  • Two Questions: Make one simple, so people get warmed up. The second one is more thought provoking.
  • Them: The questions are to be about them, not something controversial or opinion based.  Stories & experiences are best.
  • Open Ended: Not a Yes or No question. Got it?
  • Prepared: Questions on the fly equal poor questions. The best is to have the questions written down inside their Tent Cards.
  • Tent Cards: If dinner is at your house, use Table Tent cards and write the questions inside them.



  • Food: Start once everyone has their food.
  • Don’t Delay: We feel the need for small talk, don’t.  Getting to the questions quickly communicates you mean it.


  • At your house: This is ideal, because people relax more in a home.
  • Restaurant (Quiet):  If the restaurant is a cozy and quiet one, then questions can work.


You can do this. The key is believing people want to be known and you are setting the table for this to happen.

Question: What is a great question you have been asked over dinner?


  1. Four thumbs up!!

  2. It is good to have Great Friends like Art.

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