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 just one good question away from a great conversation.

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

Reuniting with old friends and loved ones has 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 chances of meaningful experiences.

If you have read about 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 on 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.

Even though no one can guarantee a single question that will always work, 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?”

“Fine.”

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 asking

“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. 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, victories… you choose. But there are some principles that I would recommend you apply to the questions regardless of 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 that is my favorite or worse whatever, color, food, music, book... I am not comfortable trying to rank all my experiences and coming up with a definitive answer. Instead of asking

“What is your favorite childhood memory?”

try asking

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

or

“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 to conversations. 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?”

try

“What made you feel this way?”

This way you're concerned, but not judging, and when they answer they are sharing, not defending. If you get one word answers feel free to follow up with a specific question such as

“Tell me more about that.”

or

“Describe how that took place.”

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

Here are some good conversation starters organized by topic.

Meaning

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

*What questions 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?"

Identity

“Describe one event that has shaped you as a person.”
“Describe a significant spiritual encounter you have experienced in you 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)

This should be enough to get you started. It could 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.

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.