The Art of Conversation: 4 Skills to Master

At first, I thought it was just me. After spending an evening with friends and never once being asked a question, or sharing some news and receiving nothing but a “thumbs up” sign in response, or receiving multiple email responses without a single acknowledgement of anything I’d said, I thought, Maybe I’m really just that boring!

But then I started hearing similar stories from others. One friend said, “My husband and I had dinner with another couple this weekend and it was like pulling teeth to get a conversation going.” Another told me, “My friend talked on and on about himself, then after asking me one question, said he had to go before hearing the answer!” Another sarcastically said, “I love going out with friends. It’s so fun to watch them use their phones.”

Conversation is becoming a lost art.

A good conversation flows freely as people exchange thoughts and ideas. It’s comfortable and puts everyone at ease. However, like all skills, being able to converse well requires practice. Here are four basic conversation skills to master. Practicing these will improve the quality of your conversations, deepen your relationships, and leave a good impression on new acquaintances.

I admit, good conversation skills do not come naturally to me. Of the four skills I mention below, the first two come much more easily than the last two for me. What about you? Which seem obvious to you? Which do you need to work on?


1) Ask Questions.

Sometimes making a comment is enough to get a conversation started. Many times, though, to begin or further a conversation you need some well-crafted questions. Ask questions to find common ground, come up with a topic to discuss, get to know the other person, demonstrate interest, or spark dialog.

Some questions do this better than others. For example, ask open-ended questions instead of closed-ended questions. A close-ended question has one answer. The answer might be “yes” or “no,” or it could be a number or date or name. Because there’s only one answer, the conversation ends there. Then you have to come up with another idea to get it going again.

An open-ended question has a more complex answer that provides fuel for the conversation to run on. Using the 5 W’s (who, what, when, where, why) can be a good starting place. In addition, phrase your question in a way that allows for multiple answers. This gets people thinking and demonstrates that you’re seeking discussion, not information. For example, “What do you do when…” sounds like you’re looking for a specific answer, whereas, “What types of things do you do when…” opens the door for all sorts of possibilities.

The goal of asking questions isn’t simply to gather data. You’re not interrogating the other person. The goal is connection. The act of conversation, volleying thoughts and ideas and questions back and forth, leads to understanding, rapport, and can build bonds.


2) Listen to the Responses.

Duh. To me, this is the most obvious step. Why ask a question if you aren’t interested in the response? Yet paying attention takes work. Most of us have our own chatter going on in our heads that distracts us from what the other person is saying. You might be running down your To Do list, wondering when the waiter will come by again, or simply thinking of how you will respond when it’s your turn to talk. It’s hard to listen to two voices at once. Shut off that mental noise.

Epictetus said, “We have two ears and one mouth so that we can listen twice as much as we speak.” Cultivate a mindset of curiosity. Everyone on the planet has something to teach you. Be ready to listen and your life will be greatly enriched.

It’s not enough to actually listen, though. You have to communicate that you’re listening. And it might come as a shock, but saying, “I’m listening,” while doing something else doesn’t cut it. You communicate that you’re listening not with words, but nonverbally. Here are some tips:


  • Use appropriate facial expressions. Usually, this is a smile. But if you’re smiling while someone is telling you about a death in the family… you’ve missed the mark.
  • Make eye contact. Not all the time, though. If you never look away, that’s called staring. Creepy! Most people make eye contact about 30-50% of the time when they’re speaking and about 50-70% of the time when they’re listening. Shoot for about half the time and you’ll be fine.
  • Keep your body mostly still. Fidgeting is a sign of nervous energy and often sends the message, “I want out of here.” Don’t fiddle with things, bounce around, pick at your clothes, etc. Be calm and present.
  • Signal that you understand. An occasional nod or “Mm-hmm,” especially when paired with eye contact, lets the speaker know you’re paying attention.

Listen. And let the other person know you’re listening.


3) Respond with a Related Comment.

By definition, a conversation is an exchange of information and ideas. It’s not just talking. Or just asking questions. Or just listening. Introverts sometimes try to get out of conversing by asking questions and letting the other person rattle on. This is a great first step, especially for those who suffer from social anxiety. Yet, to be skilled in the art of conversation, you have to speak, too.

The first step to making relevant comments is to pay attention, as mentioned above. Sometimes the conversation goes in a direction you didn’t expect, or it moves quickly from one topic to another to another. You had something witty or wise to say, but the conversation has moved on! Let it go.

The second step is to relax. You have an entire lifetime of experiences and knowledge in your head. Let go of any fears or agendas and simply be present and calm. The words will come more easily when needed if you breathe deeply and release tension. Trust yourself.

It’s also okay to pause and think in conversations. You can say, “I’ve never thought of that before” or “I need to consider that” if nothing is coming to mind. Then ask another question. Keep lightly tossing the conversation topic back and forth like a friendly game of catch. (I’m terrible, actually, at playing catch. But it does help to relax and pay attention!)


4) Share.

A good conversation leads to self-disclosure. Share a little about yourself. And let others do the same.

This might mean getting over your self-consciousness or fear of rejection. You are worth knowing. Your voice is worth hearing.

Conversely, it might mean creating a safe space for the other person to share. Asking good questions, listening to the answers, and responding respectfully and appropriately all contribute to creating an atmosphere that allows others to be and share themselves.

Self-disclosure doesn’t have to be deep. You don’t have to share the darkest moments of your childhood or your greatest current struggle. You don’t have to bare all. (Please don’t!) Simply share enough to let the other person see that you are a real person. Tell a story, give some personal background, go beyond clichés. Give the other person something to connect to.


Give and take is necessary in both business and personal relationships. A great conversation leaves both parties feeling like they received as much or more than they gave. It’s not a monologue. It’s not an interrogation. It’s not a series of awkward silences. It’s an exchange—giving a gift and receiving one in return. Master the art of conversation and not only will you feel less bored or anxious with people, your business and personal relationships will deepen and improve.


Change your communication, change your life.

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