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The Secret to Being a Great Conversationalist

Quiet Revolutionary Gregory Peart’s Story

Eight years ago, I attended a small gathering at a neighbor’s house. Before long, I found myself standing in a group of four guys whom I just met at the party. One of the guys was talking about his occupation—automobile engineering. Another guy was very interested because he too was an auto engineer. The third guy knew a lot about car design so he was engaged as well.

My knowledge of auto engineering is about as great as my knowledge of the history of cheese—almost non-existent. All the guys went back and forth in rapid-fire succession. I found myself quietly listening, nodding my head, and feigning interest for at least 10 minutes. Then it hit me: I was subtly being nudged out of the circle. I could have just walked away, but I wanted to get to know them. I wanted to be social. However, I couldn’t get a word in edgewise. I also didn’t want to appear too naïve before they knew anything about me.

And then it happened. I saw an opening. One of the guys transitioned from engineering to the design of the house he just purchased. I know a lot about real estate, so that was my open window to jump through. Instead of sitting on the sidelines, I decided to take control of the conversation and asked when he bought the house. Then I transitioned to the local housing market. Another guy was interested in selling his house. Then I talked about mortgage rates and the best time to sell. I was contributing. I suddenly found myself in the driver’s seat. They were playing in my sandbox.

If you’re reading this, you’ve probably wondered how it is that exceptional conversationalists always know what to say. You may have asked, “Why don’t they ever struggle? Why do I take longer to respond than they do?”

The answer is: They aren’t any smarter than you—they just put themselves in positions to succeed. No one can always have a good response ready for any topic. But the best socializers understand one very simple concept: if you’re in the position of responding to someone else’s question or topic, you’re at their mercy (at least during that moment in the conversation). Conversationalists who initiate the conversation topic always have the advantage over people on the receiving end.

If I called you on the phone right now—right this very minute—I can guarantee myself a major advantage from a conversational perspective. I would plan on telling you my plans to go sailing this weekend. How is that an advantage? you may wonder. By introducing sailing, I’m taking control and kicking off the conversation with one of my own topics, forcing you into a more passive position. You will have to respond and make a connection to my topic and to my statements. It’s not easy for your brain to sort through sailing-related memories in a matter of seconds, especially if you don’t have much to offer on the topic or are thinking about or doing something else, totally unrelated.

I, on the other hand, may have had minutes, hours, days, or even weeks to think about what I wanted to say and how I wanted to initiate that conversation with you. I may, in fact, be a professional sailor. Or I may have had many previous conversations about sailing that helped me develop a giant arsenal of sailing anecdotes, facts, and opinions ready to “float” into any conversation.

The comfort level I have with the topic will manifest itself as confidence. Because you have to react and exert energy, searching for related material on the spot, you will naturally be at a disadvantage and may project a lack of confidence.

Pay close attention next time an exceptional conversationalist converses with you; they are probably initiating most of the topics! The best conversationalists usually direct the show. They aren’t caught off guard or left without anything to say. In those rare cases where they are speechless, they can still ask poignant questions and eventually steer the conversation ship back to where they want it to go.

My life changed when I realized the power of this active mindset.

We all desire more confidence. A shortcut to immediate confidence is simple: go first. Be the first to ask, “Hi, how are you?” Acting first in any situation instantly boosts how confident you appear to others and, in turn, boosts your feeling of confidence. Poor conversationalists are normally reactive as opposed to proactive. They wait for something to happen to them. Exceptional conversationalists go after what they want.

Of course, action comes with risk. Staying passive is much safer and easier. Most people spend time deliberating over the negative possibilities of a potential action. But be careful: too much deliberation leads to overthinking and paralysis by analysis. Many more good things come from trying something as opposed to trying nothing. If you currently lead a passive lifestyle, you may feel that you lack control over your fate and that life happens to you instead of because of you.

It took me years to realize how often I instinctively waited for the other person to go first as if I were not allowed to dictate the conversation. After taking that initial step of acting first, you’ll feel not only an extra boost of confidence but also an infusion of happiness. Because when you act first to direct the conversation, you feel a sense of control. Shifting from a passive to an active mindset can truly change your world.

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  • Valissa Kelly

    This article reminds me of a similar article in respects to being the first to speak in a business meeting. The article recommended speaking first in a meeting to display confidence and leadership. Let’s say the meeting leader is asking for input or ideas. When you wait too long, the idea you have may be presented by someone else. It’s a lost opportunity to position yourself as one who adds value in meetings. As an introvert, this has happened before. Gregory, thank you for sharing your experience. It’s not easy putting yourself out there. Kudos to you!

  • Sam Harris

    It feels to me this advice is to pretend and act like you are not an introvert. This may work,however I was hoping this site would be more about accepting and even thriving as an introvert, not just how to get over it.

  • bas_bleu

    I love asking people questions as well. I think most people are flattered by the interest if it is genuine. The critical piece here is that most people listen in order to talk; it leads you in a much different direction if you listen to listen. You may not be taking control of the conversation, but you will be participating in a much
    more authentic process.

  • To those that mentioned this seeming like a competition, I understand. I offer that to some degree all small talk, especially with strangers, is disingenuous but it’s the way society is built. Also your intentions have a good deal to do with the competitive factor. If you’re being yourself during a conversation you’re being genuine and want to get to know the other person then you don’t need to worry about the “control” element of initiating said conversation.

  • This method works best in situations where introductions and small talk are required. I used to do this in college in week one of each quarter. I knew I was anxious and almost talked myself out of dropping courses on the first day but I’d force myself to go. Once there I’d sit near the front (yes, that’s scary for an introvert), choose one person to sit by, say hello, introduce myself and initiate a simple conversation. I’d stop by at the end of the class and say hi to the teacher and ask a question–even just a little one about the syllabus as well. In this way I had put myself in a position to be more comfortable approaching the teacher in the future and made a connection, however surface, to at least one person who I’d usually sit with the rest of the term. By the second class I’d exchange email addresses so I had someone in place to contact in case I missed a class and needed to know what went on. It was never easy but it did make me appear more confident and helped my anxiety subside quicker.

  • Mervin Yeo

    I agree that making the first move like initiating a conversation helps a me “survive” in meetings and events where the attendees interact and mingle. It was after many years of being “left in the cold” that I realise I was missing out on some good conversations and great connections for business. It’s easy for us who had done it with a measure of success to say “Just do it!”. We cannot impose this on those who have yet to try.

  • Shemayil Lail

    Thank you. This is good advice!

  • Diane Kerrison

    seems rather contrived, I thought conversation was for sharing not control

    • Kate

      Yes I felt the same way. I thought conversation was about building relationships not winning a competition…

  • Christine Morris Parnell

    Good article and easy to read. Thanks!

  • Thank you! So very helpful. Will share this w/my introvert small business clients.

  • Teto85

    Thanks for sharing. I have had similar experiences.

  • Phillip Fine

    Good advice, although advice that makes me feel guilty, since I know that when it comes to conversations,
    I’m usually in a reactive, rather than a proactive, mode. Moreover, I know I’m sometimes hesitant to initiate conversations, given that when I’ve done so, I’ve been the recipient of some snarky comments. I guess that in this area of social intercourse, it’s important to develop a thick skin — easier said than done for an HSP!

  • Leona Roselle Paloma-Gambol

    Thank you for sharing! I always have a difficult time opening up to people and I appear shy. This is helpful!

  • Natrila Femi

    Lately I’ve been wondering whether i am an introvert or not since my very quiet friend said to me that I didn’t look so ‘introverted’ like she thought because I’m pretty good at starting conversation. Well, I don’t think that you have to be passive and only nodding at every conversation just because you’re introvert. I know well that I’m introvert by heart and need so much me-time. It’s great that you mentioned such passive lifestyle can make us think life happens to us and being so negative about it 🙂 Wonderful post!

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  • Karen DeBonis

    So interesting. I’m an extroverted introvert. Sometimes I’m great in conversations, but often not. This gives me some insight. Thanks!

    • Mon

      Karen. How does your extroversion manifest, if you don’t mind me asking. Many people don’t believe me to be an introvert because I love chatting with people but they don’t see my quiet time/side.

  • Jane Mazzola

    Such observations of which I had not considered. Very helpful learning. I do appreciate Mr. Peart’s story, analysis, & recommendations. Thank you!

  • Geny Bacho

    Great story, thanks for sharing. You inspired me!

  • mcspencer

    I’m an ambi-vert, but shy, and I absolutely concur on asking questions as a conversation key (I also have a background in journalism). Either initiating (“what do you do?”) or following up in a chatting group (“Jan, you just mentioned X. [Insert question here]?”) Asking questions shows an interest in others and helps form a social bond — as long as you don’t grill people or ask inappropriate things.

  • Benjamin R

    Very pleasant to read, thank you

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  • Cynthia Dawn Clevenger

    This is great! Thank you for sharing! Although I am an introvert, I am a great conversationalist because I ask a lot of questions. I think that goes back to my training as a journalist and my career as a facilitator and coordinator. I joke that I interview people like they’re Time’s person of the year. But hey…it gets them talking! And then we can talk about anything. I live in Houston and one time I was volunteering at an event and started talking about Astrophysics with a small group of people. Mind you, I have no clue about that stuff. Way over my head!! But I like Carl Sagan if that counts?! Later on I was talking with one of those gentlemen from that group separately, and I asked him, “So what do you do?” He kindly replied, “Well, I’m an astrophysicist and an astronaut.” Of course, I would be clueless and talking to an ASTRONAUT! I was a bit embarrassed, but I responded, “Wow, that’s amazing! So when are we going to Mars?!” Like I said…I can always ask questions! 🙂