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Tips On Starting Meaningful Conversations

Tips on Starting Meaningful Conversations

Imagine being with someone you admire or care about, or perhaps someone you would love to connect with in a deeper and more meaningful way. You may have talked a few times about the weather, but nothing meaningful.

Maybe you’re one good question away from a great conversation.

As the holidays approach, people tend to spend more time together, visiting family members and old friends. We go back to our hometowns, or our friends and family members come to visit us, but whatever the case you’re likely to experience some type of reunion during the holidays.

Reuniting with old friends and loved ones have a lot of potential for great experiences—and for awkward ones. Though we cannot always avoid the awkward, there are things we can do to increase the likelihood of meaningful experiences.

If you have read about the subject of conversations, you probably already know that a good conversation is much more about listening than speaking. Don’t rehearse stories and don’t try to “one-up” someone else’s story. If you want to truly connect on a deeper level, focus on listening and do it well. Though I could take a detour to talk about listening I won’t at this time, perhaps I will cover that in a follow-up post. What I will share with you on this post is how to get the other person talking. You can be a great listener, but if no one is talking your great skills will not benefit you much.

How do you get others to talk about something meaningful?

I’m glad you asked.

Nobody can guarantee a single question that will always work, but I would like to present you with a few key principles and samples of questions that are very likely going to set you on a path towards a great conversation.

The main principle is simple, always ask open-ended questions. Avoid questions that can be answered with one word by focusing on questions that invite the person to share a story. This is trickier than at first glance because many open-ended questions can be answered with one word or phrase.

One very popular open-ended question that usually gets a one-word answer is:

“How was your day?”


Or “good,” or “okay,” or “not bad,” or “busy.” Rarely will someone describe their day to you after this question. So what can you do instead? Try being more specific, try framing the question like this:

“Tell me about one thing that went well today.”

It assumes something went well, I know, assumptions can be dangerous, but I personally prefer to focus on the positive and encourage others to do so. Even though it is fine to discuss negative events, I prefer to not start there unless I am already aware of something specific.

Different versions of this question can include:

“Describe one event that surprised you this week.”

“Tell me about one thing you are looking forward to today.”

“Describe how you handled a recent challenge.”

Making the questions about something more specific often leads to a longer, more detailed answer. In fact,  it is difficult to give a general answer to a specific question.

There are many ways to word a good question depending on the type of conversation you want to have, depending on the topic you want to discuss. Do you prefer to talk about school, work, life, dreams, family, careers, struggles, goals, or victories? You choose. But there are some principles that I would recommend you apply to these questions—regardless of the topic.

We already mentioned the first one, avoid questions that can be answered with one word.
Instead of asking “Does that hurt?” ask “How does that feel?” or some variation depending on how well you know the person. Like “How has that impacted you?” “What is it like?” “What is one positive side of it?” “What are some of the struggles?”

Also, avoid superlatives. I often have a hard time deciding what my favorite or worse thing (color, food, music, book…or whatever) is. I am not comfortable trying to rank all my experiences and coming up with a definitive answer. So instead of asking

“What is your favorite childhood memory?”

try asking

“Tell me about a positive childhood memory you had.”


“Describe a childhood memory you cherish.”

Avoid using words like “best” and “worst.” Instead of asking about someone’s “worst experience ever,” ask about “a negative experience,” or “a tough situation.”

Finally, avoid asking why.

“Why” questions make people defensive. People who are answering why questions are usually not enjoying the conversation. Instead of asking,

“Why did you go to that school?”

try asking,

“What motivated you to attend that school?”

Instead of asking,

“Why are you sad?”


“What made you feel this way?”

This way you’re demonstrating concern, but not judging. Then, when they answer they are sharing, not defending. Also, if you get one-word answers, feel free to follow up with a specific question such as,

“Tell me more about that.”


“Describe how that took place.”

With these principles, you’re bound to have better conversations. These tips will help you connect more deeply with those around you.

Here are some good conversation starters organized by topic.


“What is one significant thing that has happened in your life recently?”
“What is one thing among the best things in your life right now?”
“What is one great joy or sorrow you experienced this year?”

Questions which begin with “what” can lead to one-word answers depending on the person. In case of a one-word answer, feel free to use specific follow up questions that invite the sharing of a story.

Examples of follow-up questions (following order above):

“What makes it so significant?”
“What factors contributed to your choice?”
“How has it shaped you?”


“Describe one event that has shaped you as a person.”
“Describe a significant spiritual encounter you have experienced in your life.”
“Tell me about someone who has helped you become who you are today.”

Deep Desires

“If you could do anything with your life, what would you like to do?”

This deserves a follow-up question depending on the answer, something along the lines of

“What factors contributed to that decision?”

“What do you find yourself pursuing these days?”
Follow up: “What makes it so special?”

“If one burden could be lifted from you today, what would it be?”
(also deserves a follow-up question)

These principles and examples should be enough to get you started. It may be beneficial to make a list of potential questions you would like to ask. If you already know the type of person you will be encountering (parent, sibling, old friend, significant other, co-worker, boss…) you can develop questions that will be appropriate in your setting.

Another tip: I carry a list with me of possible questions (on my phone). I don’t necessarily open them mid-conversation, but the process of creating the list is oftentimes enough to make me more intentional bout the interactions I will have with those around me.

Was this helpful? Do you have any suggestions? Please comment below, and if you’d like, share some of your favorite conversation starters.


Guest Post by Pastor Marlon

Pastor Marlon loves Jesus! He married Vanessa, his high-school sweetheart and the love of his life. Together, they have two energetic children that they love very much. He is a Seventh-day Adventist Pastor and is currently working with the Georgia-Cumberland Conference pastoring the Park Avenue Seventh-day Adventist Church in Valdosta GA.


The Haystack is awesome. Nuff said.

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