How to Master the Art of Conversation


We all admire people who seem to bring out the best in us when we talk to them. We feel comfortable talking to them and look forward to it. If you wish you had the ability to make conversations that the people you admire have then you can also learn it. Having engaging conversations is a skill that can be learned and further developed with focus and practice.

If you know how to keep those engaging conversations flowing, you can meet, approach, and get to know almost anyone you like – generating abundant potential for friendship, fun, and shared activities. Based on my life’s experience, I think there is a pattern of behavior that keeps us from becoming engaging conversationalists.

One of these behaviors is holding back yourself until you have found something very cool, smart, impressive, and interesting to say. It kills spontaneity. Another is not knowing how to switch into the mood for conversation from something deep and serious that you may have been doing. It can take an effort to warm up and start interacting with people socially.     

You can overcome this by learning and practicing a few skills. And it is worth the effort because there are few pleasures in life better than a stimulating conversation with someone you like. You learn to transform casual talks into genuine human connections. When you really connect with someone, time stands still, space contracts, and you feel truly alive. Here are some suggestions for you to become better at the art of conversation. 

Practice active listening

People can tell when you are not paying attention listening, which is often because you just cannot wait to share your next thought. Before they have completed, you are already keen to tell them about a remarkable experience you had. Make sure to listen before you speak. If your story is really remarkable, it will still be remarkable in a few minutes. Use active listening to demonstrate your interest in what they have to say. When they see you are genuinely interested, they will be more enthused about talking to you.

Practice active listening
  • Maintain eye contact whenever they talk. Try to see the color of their iris and, if you are close, the texture of the iris. Look in between their eyes or at their eye-brows if direct eye contact feels too intense. They will not notice the difference.
  • Direct your body, feet, and head in their general direction.
  • Avoid looking distracted or watching around the room. However, when people are not talking – like when they are formulating their thoughts, it can be a good idea to look away so they don’t feel pressured.
  • Acknowledge from time to time that you have heard them.
  • Summarize what they said. They: “I did not know if chemistry was right for me so that is why I started my own landscaping business instead.” You: “Entrepreneurship was more you.” They: “Yes, exactly!”

Learn a few things about the people you meet

If you make it your business to learn a little bit about people you are going to meet, your conversations are likely to be a lot more fun. Take a look at the person’s LinkedIn or Twitter account to get an idea of their tone, interests, etc. You are likely to be at an advantage when you know more about a person. It becomes easier to relate to them and you might avoid an awkward conversation or two.

If the conversation you are in was not preplanned, then you can ask questions about them at opportune moments during the meeting. Find out simple things like what they do for a living, where they are from, or what their future plans are. Ask these things when it seems natural. It will give you a reason to talk to them and may nudge the conversation towards a common interest. 

Focus on conversation and not on your thoughts

What other people say may trigger a train of thoughts in your mind. For example someone says “I was in Paris last week” and it may get you thinking about your last visit to Paris or about your plans to visit Paris. Catch yourself doing it and bring your focus back to the conversation in the present moment. It is easier to be curious when you focus on conversation rather than yourself.

The best way to make a conversation interesting is to be more interested in your conversation partner. If you are running out of things to say, you are not interested enough in the person you are talking with. If you do not care about the person you are talking with, it will show. So your own attitude is the first thing to fix. To express a genuine sense of interest, you have to emote. Lean forward. Make eye contact. Show them that you are listening and you care.

Find topics of common interest 

If you are able to discover a topic you are both interested in, the conversation will turn interesting for both of you. If they do not seem enthused, you can try with another subject a bit later. You might come across a topic of common interest more often than you think.  

Find topics of common interest 

Try to discover something the other person is passionate about that you are also interested in. That way, the person is more open to talking in-depth about the subject and a genuine affinity can be built. While you are looking for a more enthusing subject, build conversation around mundane but readily available topics. Many such topics can be offered by your surroundings. For example: 

The location or the venue. Look at your surroundings and talk about them. Is this a beautiful hotel, a house, or a restaurant? Maybe one of you is in a new city and you can talk about what you find noteworthy about the town. Or talk about some place you visited recently.

Entertainment. You can talk about something you have enjoyed lately or something that is on your list. This could be a book, a Netflix show, a game, a movie, a play, a podcast, or a talk that either of you have enjoyed.

Art. If you are interested in art and the person you are talking to matches your interest, ask them which museums they have gone to or would like to visit. Tell them about your favorite exhibits and the artists you like. Find out which genre and medium of art they prefer and how their interest in it developed. Ask if they have any recommendations for galleries. Discuss new trends and changes in the art world. 

Food. Food is the common language of entire humanity and offers a topic that is never out of place in an informal setting. Talk about the type of food they like. Ask which restaurants they would recommend and the dishes you should order there. If they like cooking, ask which dishes they like to make.

Leisure. Delve into the other person’s hobbies. Ask what they do in their free time, which activities they participate in outside of work. If they have a passion, they will be enthused to talk about it and this may be your door to a deeper connection.  

Sports. Some folks can talk about sports all day. If you are in a group, make sure everyone enjoys the conversation and you do not have a few bored spectators as two people talk about their favorite sports. Sports often engenders passions, change the topic if someone starts getting riled up. 

The weather. Weather, like food, is another universal subject. It is generally not a stimulating subject but a little ingenuity can help you spark an engaging discussion as a precursor to something deeper. For example, ask about the other person’s plans given the weather and then move on to the plans. You can also talk about their favorite type of weather, this also frequently leads to more interesting discussions about their personality, activities, or places. Weather also helps you build discussions about seasonal rituals and traditions. Do they do anything special this time of year – trips they take, people they see, or other activities they undertake?       

Travel.  Asking if they have traveled anywhere interesting lately can open up various possibilities. This topic has the potential to get even the most reserved people pouring out cherished memories or exciting upcoming adventures – from their memorable journeys, to big summer vacations, to weekend trips an hour away or their bucket list.

Ask good questions to exhibit your interest

One of the best ways to demonstrate your engagement is by showing curiosity for what the other person is saying. Ask at least one question before moving on to the next topic. Harvesting details makes it more probable that you will be able to create a connection with the other person or find a way you can be of interest to each other.

You should know to ask questions in a manner not to turn the conversation into an interview. Use a statement without an interrogation mark at the end. For example, instead of “Did you like it?” say “Sounds like you liked it!” Then give a pause, waiting for the other person to comment. You will make the other person feel understood and that will help you two connect well.

Return to an earlier topic when a topic dies out

A good conversation is not a linear exercise. It is totally normal to go back to an older topic if the current one feels done and there is a bit of lull. For example, “By the way, you mentioned that you are looking for a new job. How is your search going?”

Tell stories

We humans are hardwired to like stories. The moment somebody says, “So, a few years ago when I was in Rome…” or “Did I tell you about that incident…” our eyes light up and our brains dial in. People who are good at telling stories are often in high demand. Stories also make people close to you as they make it easier for them to relate to you. People with loads of stories to tell do not essentially live more exciting lives, they just present their lives in a more interesting manner. Some of the ingredients of a good story are:

It has to be relevant. Have a large stock of stories so that you can find one to tell on most occasions. Stories are timeless, a good story can and should be told several times as long as there is a new audience.

You are not the hero. Talking about how good you are generally puts people off. Instead, stories that betray vulnerability are likelier to endear you to people.

Explain the context. Help people relate to your story by explaining the setting and the characters.

Keep it understandable. Talk about things or topics that others can understand and relate to. Adjust your stories according to the audience’s understanding. 

– End your story with a punch. It can be a small crescendo, but your story has to end on a high.

Know to move from small talk to more interesting conversation

The simpler you keep the initial conversation, the better it will flow, because it reduces the risk of gaps and awkward silences. A common mistake people make is looking to come up with something clever to say already in the initial conversation. No, clever quips do not constitute an engaging conversation. An interesting conversation is created when both parties talk about something they enjoy discussing. Make eye contact with the other person and let them have your full and undivided attention as you move the conversation to a deeper level.

Get around small talk by asking a personal question about the topic

Get around small talk

As we discussed in the preceding point, every meeting needs a few minutes of small talk for limbering up at the start. But if you see the discussion getting stuck in valueless chitchat, you can bring a little substance to it by asking something personal without abruptly changing the subject. Here are some examples:

– If a conversation about unemployment rate is reduced to meaningless whining, you can spice it by asking, “What would you choose if you changed your job?”

– If they do not like their job, you can ask, “What do you like doing the most when you don’t work?”

– If complaining about cold weather goes on, you can ask, “Where else would you rather live?”

– If it is merely bitching about the government, you can ask, “What would you do if you were voted in to head the government?” 

– If someone says they are a teacher, you can ask, “What do you like the most about being a teacher?”

Ask open-ended questions

You can get others to share more by displaying an interest and asking open-ended questions to help them get deeper into the conversation. Good questions are asking someone how they think or feel about something that they are talking about. If you have talked to someone before, ask them about things that they mentioned in the conversation before. Likely, if they brought up something on their own, it is of interest and some importance to them.

Ask yourself what other areas that are related to their interests that they would love to talk about. When you ask someone a question, be aware of how the question is phrased, and always bow to open-ended structure in your phrasing of questions rather than ones inviting a simple yes or no answer.

To ask questions that cannot be responded with a simple yes or no, find questions containing “what, why, when, how.” Those questions often require deeper and more meaningful answers. For example:

They: “I am from Saskatoon.”

What: “What is it like to live there? What do you like the most about it? What was it like to move?”

Why: “How come you moved?”

When: “Are there times you miss home? When did you move? Do you think you will move back?”

How: “How do you find it here? How will you compare living here with that in Saskatoon?”

Ask about their dreams

Asking about one another’s ideas and ambitions makes conversations more stimulating. You might also find that you have dreams in common. Get out of yourself and make it about the other person. Show a genuine interest in them, their world, and what they might be passionate about. Most people love to talk about themselves.

Seek their personal opinion

People usually like being asked for their opinion. For example, “I am expecting to move in with two friends. Do you have experience of co-living?” or “I am about to take my vacation. What’s your favorite way to wind down?”

Use the other person’s name frequently

Everybody likes the sound of their name, it is comforting and euphonious. Every couple of sentences, drop the other person’s name. At the start of a statement, at the end of a question – drop it like it is important.

Show pleasant body language

 Our body language plays an important role in how others perceive us. Body language that is friendly and welcoming will draw others to you and make them comfortable talking to you. Some of the important elements of your nonverbal behavior that attract others are:

Smile. A sincere, friendly smile makes others comfortable. Wear an easy going little smile as you move around. After you make eye contact with someone, give them a more wholehearted smile. 

Use open posture. Do not stand at an angle with your arms crossed or buried in your pockets. Instead, face others directly and let your arms hang naturally by your sides.

Lean forward. When you lean in while listening, it shows that you are paying attention. Respect people’s physical space. How close you can lean will depend on your intimacy with each person.

If you shake hands, do it heartily. While a question mark hangs over handshakes in the post-Covid-19 world, they may resume one day. When you do shake hands, do it well with the web between your thumb and pointer finger meeting theirs. A good handshake communicates confidence and vitality.  

Make eye contact. Making assured eye contact betrays your self-confidence and builds intimacy with others. 

Acknowledge. When you are listening to someone, nod from time to time and use other forms of acknowledgement like “hmm” or “I see.” This shows you are centered on what the speaker is saying.  

Dress properly and be well groomed. Dress well but do not over dress. That makes you seem uptight. Wear clothes that exhibit your own style and lots of confidence. 

Mirror your partner. People feel more at ease and are likelier to be charmed by those who match their style – body language, tone of voice, talking speed, and so on. Do not mimic, instead follow subtly. If your partner speaks softly, bring your voice down a notch. If they display high enthusiasm, reflect their energy. 


These are some techniques to help you become an interesting conversationalist. Do not get overexcited and try to use all of these techniques all of the time. Start with choosing one or two for each occasion and practice them until they become automatic. The more often you do it, the more comfortable you will become. You will also learn which topics generate the best conversations when, how to judge a person’s mood and character by their body language and tone of voice, when to move to new topics, and the signs a conversation has wrapped up.

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