Art of Conversing: Do You Meet these 10 Rules of a Great Conversationalist?

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Are you a good conversationalist? What makes someone a good conversationalist?

Being a good conversationalist is important in every context, be it in business, social, or dating. In the past years, I’ve met a lot of people under different contexts. In particular, my seven-month world trip last year propelled me into hundreds of social circles all around the world. Networking events have long become a norm to me as a business owner and self-directed individual. My recent dating immersion has put me in more dates in one month than I had in the six months prior to that.


With every person I meet, I find that the quality of interaction between me and the person is tied to two factors. Firstly, the compatibility of our values; secondly, the individual’s finesse as a conversationalist. (Of course, my own conversational skills comes into play as well, but since I’m the constant in all my interactions with other people, I’ve taken that out of the equation.)

I’ve met people who are great conversationalists, and we would hit it off right away when we meet, with endless topics to talk and connect on. The energy during the interaction would be undeniable. Sometimes, it would even be explosive. These people are great joys to speak with because they are self-aware, sensitive, and socially aware.

I’ve also met people who seem socially inadept—conversations would either (a) unfold like a jerking car with one-way questions and mono-syllabic responses, (b) trail off into awkward pauses ever so often, or (c) turn into self-indulging monologues. Unfortunately, conversations with such people can often turn into painful intermissions which I would no sooner want to get out of.

I recall a socially awkward person I met while I was in New York. While he was highly intelligent (he was a senior analyst in a MNC), he didn’t seem to have a very high emotional quotient. He kept asking me questions and trying to probe into my life, as if we were in an interrogation, while incessantly deflecting my questions about him. I also recall a distasteful conversation I had recently with someone who was highly combative. He would, time and again, spin my comments into mini-debates, put down my point of views, then share drawn-out arguments to support why I was wrong and why he was right—even though I didn’t ask for them. Both encounters left me with a sour aftertaste. Needless to say, I didn’t stay in touch with either individual.

How to Be a Great Conversationalist: Ten Essential Rules

Given that conversing skills is a must-have in today’s world, I thought it would do well to have a piece on how to be a great conversationalist, since I have not written about communication before.

While I think there is much for me to learn in the area of communication, I’ve been consistently told by friends and acquaintances alike that I’m a great person to speak and relate to. Often times, people tell me that they can’t help but share stuff with me that they don’t ever share with others. I also often have a knack for having drawn-out conversations that could go on forever if not for prior engagements that I and/or the other person have to attend to.

I don’t think there are any “tricks” or shady techniques you have to apply to be a great conversationalist. Below are ten timeless rules I apply to all my conversations:

  1. Be genuinely interested in the person. Who is this person? What’s on his/her mind? What does he/she enjoy doing? What motivates him/her in life? These are the questions I have for every single person I meet. Since people make up my life purpose (to help others achieve their highest potential and live their best lives), my genuine interest in people, from who they are to what they do, comes naturally. 

    Such genuine interest, not an artificial one, is essential to making a conversation fly. Even if you execute rules #2 through #10 of being a great conversationalist to a tee, the conversation will still fall flat because there is no driving force behind the exchange.


    So, have a genuine interest in everyone you speak to. If you are not interested in the other person, then why speak to him/her to begin with? Move on to someone you really want to talk to. Life is too short to be spent doing things you don’t like.

  2. Focus on the positives. Go for the positive topics. Which means rather than talk about past grievances, opt for a discussion of future goals. Rather than talk about the coffee that spilled on your table this morning, talk about that movie you are looking forward to watch later in the evening. It’s okay to talk about “negative” topics (read: topics that trigger negative emotions) once in a while, but only when you feel it is okay with the other party and when it has a specific purpose (e.g., to get to know the other person better or to bond with the person).

    During your conversations, always adopt a forward-thinking mentality. Less complaining, more solutions. Less judging, more empathy. Doing more of the latter will make you a more enjoyable person to speak to. Doing the former will turn you into an energy vampire.

    Principle #4 of 10 Timeless Principles for Lasting Happiness teaches you how to see the positives over the negatives in every situation.

  3. Converse, not debate (or argue). In the article opening, I mentioned this recent conversation I had where the guy was highly argumentative. Rather than treat the conversation as a fun, enjoyable exchange, he kept picking on stray comments and turning them into elaborate me vs. you arguments, when the discussion didn’t matter to me either way. Needless to say, the conversation quickly dwindled into nothingness. His combative and demeaning tack was so draining that I didn’t even want to speak to him after fifteen minutes.

    A conversation should be a platform where opinions are aired, not a battle ground to pit one’s stance against another. Be ready to chat, discuss, and trash out ideas, but do so amiably. There’s no need to have a conclusion or agreement point in every discussion; if a convergence has to be met with everything that is mooted, the conversation would be very draining. Allow for things to be left open-ended if a common point can’t be achieved.

  4. Respect; don’t impose, criticize, or judgeRespect other people’s point of view. It’s fine to express your opinion, but don’t forcefully enforce it on them. Respect other people’s space—don’t encroach on the person’s privacy unless a common bond has been established. Respect other people’s personal choices—don’t criticize or judge. To do otherwise in each instance would be to impose yourself onto others when it isn’t your place to do so. Remember, everyone has his/her right to be him/herself, just as you have the right to be yourself.
  5. Put the person in his/her best light. Always look for ways to make the person look good. Give credit where credit is due. Recognize talent where you see it. Drop compliments where appropriate.  Allow the person to shine in his/her own light. A lot of people don’t recognize their personal prowess and it’s up to you to help them do that. Be their guide; be their conduit to love.
  6. Embrace differences while building on commonalities. Everyone is different. At the same time, there are always commonalities across people. For the differences, embrace them. They make all of us unique. Agree to disagree if there are clashes in ideas. As you talk to the other person, look for commonalities between you and him/her. Once you find a common link, build on it. Use that as a platform to spin off more discussions which will then reveal more about both of you. For the new commonalities that get unveiled, build on them further.
  7. Be true to yourself. Your best asset is your true personality. Embrace it and let it shine. Don’t cover it up. It’ll be pretty boring if all you do is mime the other person’s words during a conversation; there wouldn’t be anything to discuss at all. Be ready to share your real thoughts and opinions (not in a combative manner of course—see #3). Be proud of what you stand for and be ready to let others know the real you. Read: Finding Your Inner Self
  8. 50-50 sharing. I always think that a great conversation should be made up of equal sharing by both parties. Sometimes it may be 40-60 or 60-40 depending on the circumstances, but by and large, both parties should have equal opportunities to share and contribute to the conversation.

    What this means is that you should be sensitive enough to pose questions to the other party if you have been talking for a while. (See #9.) It also means that you should take the initiative to share more about yourself if the other party has been sharing for the most part. Just because the person doesn’t ask doesn’t mean you can’t share; sometimes people don’t pose questions because it is not in their natural self to do so.

  9. Ask purposeful questions. Questions elicit answers. The kind of questions you ask will steer the direction of the conversation. To have a meaningful conversation with the other person, ask meaningful questions. Choose questions like, “What drives you in life?”, “What are your goals for the next year?” and “What inspired you to make this change?” over “What did you do yesterday?” and “What are you going to do later?”. Try out the questions in this list for a change: 101 Important Questions To Ask Yourself.

    Some people may not be ready to take on conscious questions, and that’s fine. Start off with the simple, trivial, everyday questions as you build a rapport. Then, get to know the person better through deeper, more revealing questions—when you think the person is ready to share.

  10. Give and take. Sometimes people say pretty weird stuff during conversations. For example, a critical comment here and there, a distasteful remark, and a bad joke. Don’t judge them for those comments; treat these blurts as Freudian slips. Give them the benefit of doubt (unless clearly proven otherwise). I myself make random oddball comments sometimes which leave me wondering why I even did that afterwards. Usually I just laugh or shrug it off; it makes for funny conversation banter.

What’s Makes a Great Conversationalist to You?

What do you think makes a great conversationalist? How can you apply the ten rules to be a better conversationalist?

Be sure to check out these other articles in the interpersonal communication series (links below)!

Get the manifesto version of this article: [Manifesto] 10 Rules of a Great Conversationalist

This is part of a series on interpersonal communication.


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