Learning to be a Better Conversationalist

Shyness & Social Anxiety Guy

A good conversationalist is a very important skill in every aspect. Being an introvert person, I have always been fascinated with talking to people. More specifically, what to say to people. During my high school and early college years, I was painfully shy and rarely say anything to anyone, mainly because I would never know what to say to people.

After college, I did pick up a few books on conversations. I have to say they really help, even if it’s all mental. However, I find myself forgetting most of the lessons from these books and sticking to only one trick: ask questions. Great for the initial few minutes, the problem is that I have fallen into the trap of machine gun questioning, which always makes people feel awkward. So I decided to learn new, and relearn old, conversation skills to become an interesting conversationalists.

I figure that I’ll share what I learn during this process of self improvement. Generally, a good conversationalist does not dominate the conversation but asks questions, listens, and responds to the speaker.

Asking questions:
This is the obvious one. However, asking questions one after another in succession can make the other person feel awkward, as from my experience.

Start with simple, non-threatening questions about the person to start the conversation going like “How they know the host/mutual friend?” or “Do they live around your here?” If you know the person’s interest, you can ask about their interest like “How your fantasy league doing?” or “How’s your sewing coming along?” As you get to know the person better, you can move to more interesting questions about themselves like “What is one or two things they would like to accomplish if work and money was not a factor?”

Of course, add some of your insights and opinions in between questions to avoid sounding like a questioning machine, like me. Be sure to ask them what they think when you’re sharing your thoughts or transiting the conversation to another topic.

Ask some follow up questions to gain a better insight and clarification on what the person is saying and the person’s life. These questions help the person know that you’re interested in what they’re saying and the happenings in their life. Follow up questions can be simple as, “How did you feel when that happened?” or “What did you do next?”

Generally, people like good listeners because they make the speaker feel interesting and validated about themselves. Of course, being a good listener is not just being an ear for someone while looking bored.

Show interest by asking follow up questions like “What you mean?” or “How do you feel about that?”

Provide some feedback to the speaker. I fall to this myself at times. In my attempt to concentrate on what’s being said, I develop a blank face. The other person will notice and see it as you are not interested on what’s being said. I find nodding and some facial expressions can go a long way. Most importantly, be genuinely interested in the person. Move on to someone else if you are not interested to save both parties time and energy.

As such, I feel providing feedback is a critical skill that separates the good listeners from the average listeners. I notice that when I run out of steam in providing feedback to the speaker, the conversation usually ends, awkwardly at times. Some of my more animated and energetic friends can keep the speaker energized and the conversation going. Of course, this takes practice and knowing when to end the conversation and re-engage them again when you, yourself, is re-energized.

Keeping with current topics:
Keeping on top of current events in entertainment, sports, and politics can be very useful when conversing with someone. Entertainment and sports are obvious good choices to keep updated in as they are easy and not as controversial as politics.

I usually scan the news before bed on my phone on sites like Google News. I also follow a few websites that cover certain topics that interest me like video game.

Watching movies, reading popular books, and following a few sport stories will help your arsenal of conversation skills. Who does not want to discuss the latest episode of Games of Thrones? Of course, you don’t have to watch every movie or read every book, just a few so you can add to the conversation when people ask about your interests.

With politics, you can try to add some humor but being careful to not offend people around you. Of course, you do not have to agree with person, make sure your points with evidence, conviction, and a dash of humor if possible.

Being humorous:
Speaking of humor, witty comments can break ices and uplift the conversations. Not an easy skill to develop because good witty comments are spontaneous, clever, and unexpected. If you happen to know a witty person, try to observe the person and pick up a few tricks. Everyone appreciates a person that can make them laugh. I definitely need work on this, myself.

Having a few stories in your pocket can be helpful. Funny personal stories relating to unusual experiences and misfortunes are good. Self-deprecating stories can be funny as well. You should practice these stories but do not force them into conversations. You will learn to fine tune and time the delivery of the jokes over time.

Jokes and witty remarks that you borrowed should not be used without asking the other person. In addition, you should not finish or give away someone else’s punch line.
Most importantly, be yourself and enjoy the interaction. Being natural and relax with a positive attitude will attract more people around you. Yes, talking to a stranger can be scary but who knows, some of those interactions can be one of your life long friend, companion, or a future job opportunity.


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1 Comment

  1. Thanks very interesting blog!

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