How to Have a Meaningful Conversation

Asking Meaningful Questions

Ask personal questions. Asking personal questions works best in a casual setting with a friend or two and may not be appropriate for all settings. However, asking personal questions is one way to get to know someone better and in a more in-depth way. Personal questions show that you are interested and want to hear what the person has to say. Ask questions about their life and experiences. For example, ask, “What was growing up in another country then coming here like for you?” You can also say, “What was it like when you volunteered in Ecuador?” or, “How did you know you wanted to be a rock climber?” You can also ask, “What’s the hardest obstacle you’ve overcome?”

Discover their goals and dreams. Ask someone about their goals and pursuits. This is one way to learn what the person values and how they want to move forward. Learning about someone's goals and dreams can encourage them to open up to you and talk about things that matter quite a bit to them. Some areas to consider asking about might include career, fitness, lifestyle, and hobbies. For example, ask, “What would you like to accomplish in your lifetime?” or, “What milestones would you like to meet in the next five years?”

Learn about their family. Families shape people in ways that are often significant and meaningful, which affect them their whole lives. Learning about someone’s family can tell you lots about them. You can start out simply and then ask more meaningful questions. For example, ask, “How many siblings do you have?” and, “Do you get along with your family?” Be aware, however, that not everyone enjoys talking about their family. If the person appears uncomfortable or wants to change the subject, be respectful and do so.

Ask questions about their career. Asking career questions may be best when in a professional setting. For example, if you want to have a meaningful conversation with a coworker, ask them about what brought them to the job or what they enjoy about it. You can also ask where they’d like to see themselves or what their career goal is. For someone stuck in their job, talking about careers and what they want can be meaningful in taking a step forward and realizing that they have options. However, if the person does not particularly like their job, then you might also try asking about their hobbies. Often you may learn more about a person by asking about their hobbies than by asking about their job.

Remember your past discussions. One way to show that you care is by remembering things that are important to the other person. If you know the person has recently moved, adopted a dog, or started a vegetable garden, ask them about it. It’ll show that you were listening and interested in their life. It can also help you understand them more and open the door for more conversation. For example, say, “How was your first marathon? I know you trained so hard.”

Connecting on a Deeper Level

Ask open-ended questions. A conversation isn’t about speaking at someone, it’s speaking with someone. You’ll learn more about the person’s perspectives and experiences by asking questions. If the person tells you something, follow-up with a question that encourages them to keep speaking. Keep your questions open-ended so that the person can elaborate as they want to. A meaningful conversation is difficult to develop from “yes” and “no” questions. For example, ask, “What was it like when you got married?” or, “What was your proudest moment?”

Follow up with deeper questions. If you start out with a question, ask another one to get more information and help the person open up. For example, if you ask a general question, follow it up with a more specific question. Your questions should engage the person and help to create depth in the conversation. For example, if someone is talking about a memory, ask, “How did that impact your life?” or, “What did you gain from that experience?”

Find common interests and experiences. A simple, easy way to relate to someone is to find common interests, hobbies, experiences, and backgrounds with the person you're talking to. You may have grown up near each other, attended the same university, or watch the same television shows. Ask them about their background, and, if yours is similar, compare the two! For example, if your friend is upset about a job loss and you’ve been through a similar experience, you can relate on this and how difficult it is. Relating over difficult situations can often bring meaning and comfort to someone. Sometimes, being relatable means showing that you understand and are listening, even if you haven’t ‘been there.’ For example, you could try saying something like, "I certainly have no aptitude for physics, but I'm fascinated by people who understand it."

Be willing to be vulnerable. A meaningful conversation is difficult to build and maintain if those involved are unwilling to be vulnerable. Being vulnerable means letting a person know you are not always right, strong, or perfect. Share your imperfections in a way that does not invite pity, but that shows the other person that you understand hardship. Other ways to be vulnerable might include connecting with another person about a shared experience or memory. Be willing to open up, especially if you feel alone in something. If someone is being vulnerable with you, be sure not to judge them or criticise them for their experience. Try saying something like, "You showed great strength to overcome that obstacle." For example, if someone is struggling with depression, speak up and say, “I know how that feels. I struggle with depression, too.” This can help you connect and not feel alone.

Show that you care. A meaningful conversation doesn’t necessarily have to be a long or in-depth conversation. Show that you care by extending your support or help to someone. Small gestures can mean a lot, so celebrate the person’s milestones and show that you’re there for them when they hit a low point. For example, share your excitement at a birth announcement or job promotion. Send your condolences when the person is grieving. Offer your support and help in a way that is meaningful to them, whether that be a text message, email, or in-person conversation.

Listening Well

Practice active listening. Instead of thinking about how you're going to respond, take the time to listen and attempt to understand their words while the other person is talking. Pay attention to what they say, the feelings they express, and what they communicate through their body language. If you don't understand something they said, or if you're going to directly respond to one of their points, repeat what you think they said back to them first and ask if you understood them correctly. Sometimes being an active listener may also require you to be silent. Showing that you are okay with silence, even if it is a bit uncomfortable, may give the person time to gain the courage to share.

Maintain open body language. Your body can communicate to the other person that you’re listening and engaged. Nod occasionally, smile, and use other facial expressions. Examine your posture and ensure that it is open and inviting. This means uncrossing your arms and legs and facing the other person as they speak. Make eye contact and point your body toward the person, but keep your body in a relaxed position. Forcing open body language may seem unnatural.

Approach the conversation openly. Be open to disclosing information about yourself and also open about listening to the other person. If you disagree about something, be willing to hear the person out and consider their viewpoint. Instead of making your goal to “win” the conversation or be right, make your goal to better understand someone else and hear a different perspective. For example, if you tend to argue with your Uncle about politics, aim to make the conversation more meaningful by hearing each other out and being willing to consider their viewpoint.

Validate their experiences. People feel heard and understood when you show that you’re listening. When you validate someone, you show them that you accept them and that what they say is important. Validation can be as simple as saying, “That seems so difficult” or, “No wonder you’re struggling, it seems like you’re under so much stress.” Validation creates connection and safety, which are important in a meaningful conversation. Reflect back on what they say to ensure your understanding and show that you’re listening. For example, say, “I hear you saying that dealing with your aging parents is difficult.”

Creating a Safe and Comfortable Space

Choose who you want to speak with. Find someone you feel connected to and who you feel a strong connection with. It’s difficult (though not impossible) to start a meaningful conversation with a stranger or acquaintance. It might feel more comfortable to start a meaningful conversation with someone you’ve known for a while or already have some closeness in your relationship. You might not want to start a meaningful conversation with someone who’s often argumentative or focused on always being ‘right’. Think about someone you can engage with and share both speaking and listening.

Choose an appropriate time to talk. A meaningful conversation will often occur within a context that makes it meaningful. While some meaningful conversations can happen spontaneously, others may require some planning. Especially if it’s difficult to find time to meet up, choose a date and a time where both you and the other person can be present and fully engaged. For example, don’t have the conversation when one or both of you have a time constraint. Avoid busy or stressful days so that each person feels comfortable and not preoccupied or stressed.

Find a quiet place. When talking, you don't want to be interrupted by surrounding noise. You probably also don’t want prying ears overhearing your conversation. Find a quiet place where you won’t be disturbed or interrupted. This might include somebody’s home or a private meeting room. For example, a restaurant may not be ideal as you may be interrupted or overheard. Look for a place with minimal distractions. Consider turning off your phone or the television so that it doesn’t interrupt your conversation.

Collect your thoughts before you speak. If your conversations are often scattered, disorganized, or tangential, you can pause to talk a moment to organize your thoughts. This helps keep the conversation on track, and can give you a confidence boost as well! If you know you're going to have a difficult conversation and want to prepare well in advance, you can also try writing down what you want to say to organize your thoughts! Put some effort into starting the conversation, especially if it’s a difficult topic. Decide on how you will start the conversation and what words you will say.

Start with small talk. Whether you enjoy it or not, small talk can help to open a conversation and make people feel more comfortable. Starting a conversation with something deep might be jarring or unexpected, so warm up with some small talk first. When you and the other person appear comfortable, bring up a more substantial topic. For example, ask how the person’s day is going or briefly talk about the weather.