Turn Setbacks into Setups

8 Questions to Ask for Deeper Conversations

September 2, 2019

Are you constantly trying new ways to make conversation with friends and family, but find that your skills in that department seem to come up short? Maybe you’re just not asking the right kind of questions. Here, we’ll share eight suggestions to take your conversations deeper than they’ve ever gone before:


An Open-Ended Question

Keeping questions to a yes or no format is a quick way to kill a conversation. If you want to keep the exchange flowing, keep questions open-ended and allow your conversation partner to offer more details than a simple, one-word reply.


A Follow-Up Question

A follow-up question will give you more details about what your partner has to say – and show them that you were listening to their original answer.


A Reaction-Based Question

How did the topic you are discussing make your conversation partner feel when they first encountered it? Ask them as much!


A “Why” Question

Conversation experts recommend asking “why” several times during a conversation, as a way to elaborate on points and request more information from your partner. This also shows interest and keeps the conversation moving.


A Specific Question

Don’t settle for the basics when you can get the juicy details! Ask your conversation partner to elaborate and see how deep your conversations go!


A Storytelling Question

People generally love to tell stories and recount events from their own lives. Give your partner the chance to do so by asking them to tell a story related to the topic.


An Educational Question

Has your partner learned anything from their own experiences related to the topic at hand? If so, ask them to share those lessons with you. You stand to learn a lot – and your conversation partner will feel valued and heard.


A Question about What else You Should Ask

This may sound strange, but it can be beneficial to ask your partner what else you should ask them. What is something no one else thinks to ask? What have they never gotten the chance to talk about before, regarding the topic at hand? You might be surprised how much they open up to you after hearing this request!

If keeping all of this straight seems like a big task, it’s okay. Learning to be a conversationalist isn’t something that comes naturally to everyone. To learn more about connecting with others and taking your relationships to a deeper, more satisfying place, talk to an expert lifestyle coach at Hundred Life Design today. Before long, you’ll be the life of the party – or at least the most interesting person to talk to!

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