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

This is part of a series on interpersonal communication.


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 exercise 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. (Those with Personal Excellence Book, Volume 2, check out the exclusive, related article on 10 Keys To Becoming a Better Communicator, which covers communication as a whole.)

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.

Image: Conversation

  • Rob

    Great article, it’s helped me find some areas of my conversational side that I could improve.

    • Celes

      Glad you found it useful Rob. :D

  • wanxuan

    Hi Celes,

    I agree that the no.1 rule is to be “interested” in the other person. I used to think that I got to be a “interesting” person with the latest updates on news, tips, gossip etc. Most people are also worried about not being “interesting enough” I guess, maybe that is why people wanna impress and show off their cool logic ;) While having something to share is not a bad thing ( it’s good to inject some insights here and there) I guess most people rather talk about their hair follicles than what’s going on in Oprah for example. Most people’s favourite subject is themselves- so I would encourage people to talk about themselves- their interests, passions, desires etc. Anyway your pet conversational topic may not be theirs too. :P No humans are alike. Humans are so intriguing ;)

  • Christina

    Hi Celes,

    Thank you for sharing this article. I can definitely relate to some of the experiences you mentioned (I can think of an awkward and combative conversation I had this week, as a matter of fact!). In a way, by writing this article, you are helping to make the world a better place if even one person reads this and has an insight for how they can have better conversations!

    I especially liked your tips for focusing on the other person, making sure to have an even exchange, and build on commonalities. It’s sounds simple and commonsense, but most of us don’t take the time to think about what could make our conversations better. These are clear, genuine, and helpful points.

    Thanks again!


  • JadePenguin

    “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.”

    That’s where I get stuck – I tend to only get along with conscious people I can ask those questions. I don’t even know what to talk about with someone who is only ready for everyday trivialities!

    Also, I honestly do not care about someone’s last night at [club name here] where they got “so wasted”. Which is about 80% of the student population here, sadly :/ (one of UK’s top universities)

    • Celes

      Hey Jade! :D I guess that is where rule #1 will come in – be genuinely interested in the person. So I guess if the person is only ready for everyday trivialities, and you aren’t too interested in such a person, perhaps that isn’t the kind of person you should be speaking to in the first place! Where can you find the more conscious students whom you would like to connect with? Certain student clubs or societies? Faculty events targeted at a certain crowd? (Say, panel discussions, talks, about certain topics?)

      • JadePenguin

        Yep, that’s what I do :) I just keep having the feeling that dismissing 80% of people I meet is somehow antisocial or judgemental. But I’m finding more and more confirmation that there’s nothing wrong with that.

        Although I really wish I could talk to the less conscious people and perhaps get them thinking about other, more important things in life :|

        • Celes

          Hey Jade, how about not dismissing them (the 80%) and just trying to understand them as people? Like try to understand their motivation behind the seeming “trivialities” they do every day. I find that everyone has a deep side to him/her. It’s often up to us to find that. Once we connect with that part of them, it becomes much easier to move straight to the deeper conversation the next time.

          • JadePenguin

            It seems to me it’s an escape from the real world, maybe trying to fill the void that comes from not having a clear purpose. Maybe they would like to do something great but don’t know how or what they could do. They’d probably explain it “because parties are fun” – and it’s usually taken for granted that anything fun in life makes it worth living, even if the person is only a hedonist and nothing else.

            I may be wrong though – just theorising here :rolleyes:

            • Celes

              Hi Jade, sure. How can you help these individuals? What can you do to raise their consciousness? As a start, perhaps just knowing them as individuals, without any prejudgment, would help to get you guys off on the same foot. It actually feels that you might already be viewing them with a certain degree of disdain, which is not necessarily the best foot to start off (for both you and the person) if you want to have a good conversation with someone (i.e. rule #1 about genuine interest; it doesn’t feel like you have any genuine interest in them to begin with). For example, if someone is already wary or dismissive of what I do in life, I wouldn’t feel comfortable or interested to talk to him/her, because I would want someone I speak to to respect me as a person first before I engage in communication with him/her.

  • Christina

    Hi Celes,

    Thank you for sharing this article. I can definitely relate to some of the experiences you mentioned (I can think of an awkward and combative conversation I had this week, as a matter of fact!). In a way, by writing this article, you are helping to make the world a better place if even one person reads this and has an insight for how they can have better conversations!

    I especially liked your tips for focusing on the other person, making sure to have an even exchange, and build on commonalities. It’s sounds simple and commonsense, but most of us don’t take the time to think about what could make our conversations better. These are clear, genuine, and helpful points.

    Thanks again!


  • Bob

    What’s Makes a Great Conversationalist to You? Enthusiasm about a subject, someone who loves what they are talking about. They describe the subject with such detail that they bring it alive. You can see their eyes sparkle in delight as speak describing their topic. The audience shares in this participation as you feel for the speaker as they delve into their story deeper, describing the activities and adventures they have had along the way. They have a wide variation in delivery from making noises, movement to changing the pitch and tone of their voice to give effects and make it real.

    I think a great conversationalist is made by:
    1. A loving ear being interested in what is being said.
    2. An excellent range of vocabulary which helps to define and refine the ideas breathing life and movement into each and every conversation.
    “A powerful agent is the right word. Whenever we come upon one of these intensely right words… the resulting effect is physical as well as spiritual, and electrically prompt.” – Mark Twain
    3. Making people feel good about themselves, that you are happy to hear them and what they have to say. This could be compared to be loving with a dog, the dog knows if you are not genuine and isn’t fooled, it is the same with people, they can feel your intentions.
    4. Building bridges sharing feelings – I felt the same way to when I was…it opens the channels of communication, listening, sharing ideas and thoughts. Caring and sharing allows space for person and conversation to develop.
    5. Preparation beforehand, if this isn’t possible it can be done by asking some closed questions to see what a person likes and dislikes to open up the conversation. Then moving to more deeper questions. Reviewing after what went well and what needs to changed for this person, everyone is different. If you meet them again.
    6. Being a candle and a mirror. There are two ways of spreading light, to be the candle or the mirror that reflects it. Giving hope and reflecting the brilliance of others.
    7. Win-Win each person gains from the perceptions insight of the other.
    8. Breathing life into each others dreams.

    How can I apply the ten rules to be a better conversationalist?
    I have started applying them already, I especially love your first 4 questions Celes – simple and powerful.
    Who is this person?
    What’s on his/her mind?
    What does he/she enjoy doing?
    What motivates him/her in life?
    In each of your rules I have something to learn or remind myself how to improve!

    Thank you again Celes for a superb article, you set the standard high and will certainly help me to raise my standard of communicating.

  • Will

    These are all great tips and I’m always looking for ways to improve my conversational skills. This area has always been my weak point, but it’s also an area I like to focus most of my attention on because of that.

    I completely agree with your first point. I’ve realized over time that people love talking to others who are genuinely interested in what they have to say. I guess everybody wants to feel that their opinions matter.

    Thanks Celes!

    • Celes

      No problem, Will! I’m glad you found this post helpful. :D Thanks a lot for your kind comment!

  • Matt

    I might have some awkward exchanges from time to time. Sometimes I want to communicate a certain message but I have trouble finding the words. This can be very frustrating. It often feels something like this.

    After reading this I realize it’s because I was completely ignoring rule #1 in your post. If there is a weird pause, a bad joke, or I just feel like I have run out of things to say it’s because I am more interested how I am coming off to others than what is going on with the people I am interacting with. Sometimes I want to sound smart or impress others but this usually backfires. It’s actually very self absorbed to be thinking that way during a casual conversation. From now on I will definitely keep the four questions from rule #1 in mind when speaking with people.

    I absolutely agree with #2 as well. For example I have a coworker who is very negative and will almost exclusively only talk about the frustrations of our job. One day while I was in the lunch room he sat down with me to eat. He immediately began speaking about a poor interaction he just had with a customer. It was difficult for me to interject any replies. I felt trapped in the conversation. I eventually interrupted him and asked about his family. He mentioned he has a young daughter and I probed more into that. He began speaking about enrolling his little girl in school this fall. Once he was talking about his daughter he lit up from someone who seemed very bitter to someone who very much cared for his children. It was quite a transformation to watch and I was glad I could steer the conversation to more positive topics.

  • Sarah

    Like that you included not judging. I think we lose a lot of relationship quality by making decisions based on the hypotheses in our mind rather than bothering to learn what a person is really thinking. Speculation is a ceiling.

  • Stephen

    These are some good tips thank you for writing them I really need to learn #9! People tell me I’m good at conversations – when I finally get purposeful questions lol! I’m glad my life experience has lead me to reach similar conclusions to you with those tips that encourages me to believe these truly are good tips to follow!

    Usually when I have conversations the first thing I do is try to listen carefully to what the other person(s) are saying, that may seem so obvious but it’s amazing how most people in my life hardly listen to each other. Over here in England we seem to live in a very “busy” society and I feel it’s important to have peace from within and take the time to properly listen to others. That fits in nicely with #1 on being genuinely interested. I can’t agree more that it’s important not to be artificial and remember we all have hearts as well as brains – there are a lot of people with that “right wrong” mentality similar to that person you were talking with and that type of thinking is almost like a disease.

    When entering a conversation with energy vampires I realized we don’t have to give our energy away to them. If they choose to be angry, bitter, negative or something that seems to absorb our energy, we can actually choose to stay joyful and calm. It’s a matter of developing a new habit and attitude that goes against what the tv programs and media typically teaches us (i.e. we can only be calm when life goes perfectly, which is a lie).

    I use to have all my energy absorbed around these types of people (sadly there were a lot of vampires in my life). Eventually I realize “hang on, what is my intention when talking to these people?”. If I have a good motive, I realize I SHOULD be happy and joyful with myself for trying to start decent conversations with them regardless on how they react. This again ties in with listening to my inner voice in my heart which confirms to me I should receive joy if I give have intentions while having a conversation with any person!

    Since I developed that attitude, no energy vampire has been able to absorb my energy, in fact I now seem to have more energy no matter who I talk to which is great. It’s actually requires daily work to keep my mind to align with this type of thinking but it’s really been worth it for me.

    I really like your tip #4, we should show love and respect to everyone. In some situations that’s easier said then done but again it’s about changing bad habits to good habits.

    I hear a lot on “being positive” and I’ve met people who feel it’s better to be positive and people who feel it’s better to be negative. I recently realized those who tell me it’s good to be negative think the positive thinking people were not observant and reality enough while those that tell me it’s good to be positive said the negative people were depressing and they feel their energy gets drained away around them.

    I actually took a step back to that and realized there is a bigger picture here! There are good attributes and bad attributes in BOTH of those type of people! I think being observant is important, but we should be positive and look at the bright things while at the same time being realistic (not unrealistic) about our situations. Although it’s still good to always be hopeful! So when people ask me if I’m positive or negative I now tell them why not take the good traits in both types of people?

    It’s the same with being optimistic or pessimistic, both types of people usually have good and bad qualities, so stay positive like the optimistic but be observant and realistic like the pessimistic! (And take out the bad stuff, so don’t be unrealistic or negative! lol)

    I also feel we should not purposely try to avoid negative topics or feel uncomfortable at the idea of a negative topic, because I also realized what matters is what we express from the heart more than the topic itself!

    I truly believe we can have both positive and negative topics but always express them joyfully, then positive energy emits. So with the example you gave, it’s good to avoid talking about the spilled coffee if it’s expressed negatively, but it could be expressed in a fun child-like joke manner therefore become a negative topic expressed in a positive way.

    I need to get better at explaining what my point is through typing, but the bottom line is it isn’t the topic that matters but the emotions in the heart we use to express the particular topic.

    Does that make a bit of sense? It’s worth practicing that technique in some conversations and see what your experience with that is like. In my life it took away any worries or fears I may start a “negative” topic and kept me a lot happier knowing anything I mention can be expressed positively and joyfully in the heart.

    I thought it may be worth sharing my opinion and feedback from my life experiences so far. I hope it can help.

    Ps I’m also not against energy vampires or people with “right wrong” mentality, I just mean the way they start conversation could be better and actually can do mental and emotional harm to people who don’t know to respect themselves.

    Thanks for these tips Celes!

  • Iain McGregor

    Thank you for your article. The same rules apply to a partner relationship (or any other) be it a conversation or a way of being with them. I guess it covers a way of being for yourself and after that you have no control.

    Thanks again for the stimulating article.

    • Celes

      Hi Iain, you’re welcome. :D You’re definitely right that the same rules apply in any relationship, to any conversation.

  • jamie flexman

    I love this article, well thought out and explains everything really well.

    I think it’s also important not to focus too much on what you want to say next, instead react to what they are saying. You can see this in the best interviewers as they aren’t waiting, they are engaging.

    • Celes

      Hi Jamie! I love what you have shared. I see it as being in the moment and focusing on the conversation that is taking place now, which is what a conversation is supposed to be anyway. Some people worry about what they should say/ask next, perhaps because they want to convey a positive image of themselves to the other party, and unfortunately miss the point of having a conversation altogether.

  • Pingback: Ask Celes – How Can I Stop Feeling Lonely? | Personal Excellence

  • Pingback: Cooped Up Indoors Every Day? Get a Life with These 7 Tips | Personal Excellence

  • Pingback: How I Used to Be Afraid of Intimidating Men and Why It Does Not Faze Me Anymore | Personal Excellence

  • Pingback: How To Make Small Talk with Anyone in 5 Easy Ways (Examples Included!) | Personal Excellence

  • Pingback: Ask Celes – How Can I Be More Street Smart? | Personal Excellence

  • Pingback: Hate Awkward Silences? 10 Essential Tips To Be a Great Conversationalist - Lifehack

  • Pingback: What to Do When You Live in an Angry Household: 6 Tips | Personal Excellence

  • Pingback: Ask Celes — How to Keep Calm and Make a Good First Impression in 15 Minutes or Less | Personal Excellence