how to be a great conversationalist

How to Be a Great Conversationalist-Even if You’re Shy

How do great conversationalists do it? How do they know how to connect with people and make them feel good? How do they diffuse difficult situations so well and make everyone feel great?

We’ve all been there, right? That time on our first date when we had no idea what to say? Wracking our brains for something interesting to bring up? Feeling like an idiot!

How about at the party where everyone seems to be having so much fun. You’re standing by the hors d’oeurves, wondering how to chat with someone, anyone!

Before the meeting starts, you’re trying to think of something more creative to say than, “What’s up with you?”

Great conversationalists know that speech is music. And second, speech is power. Using your communications skills, you can establish strong relationships with folks, have people adore being around you-leading to incredible success.

  1. Tell stories containing human emotion. 
  2. Be completely relaxed. 
  3. Love your audience to extinguish shyness or introversion. 
  4. Compliment, don’t comment. 
  5. Use influential intonation. 
  6. Listen, rephrase & repeat. Show empathy. 
  7. Be kind and be brief. 

how to improve your communication skills

The best thing you can do is to get people talking.

And I don’t mean by asking them questions. Nobody but the few that will talk your ear off anyway want to be in the hot seat.

Tell short stories that contain human emotion. I recommend arming yourself with an arsenal of anecdotes. Put some time in and think about your life experiences that have a moral or some human interest. 

Then practice those stories until you’re confident and they feel good. Make sure they’re not longer than about thirty seconds. Shorter is better.

Resist the desire to give a lot of detail. The best stories draw broad strokes so your listener can draw their own picture in their mind. That’s how people feel connected to you. 

You can apply this to your elevator pitch.

How does telling stories get people talking?

Good question, glad you asked! Yes, it does! If your story contains human elements, folks will jump at the chance to tell their own story, the one yours reminded them of. 

You know the feeling; you’ve done it before. When a friend told you a story you related to, you hastily told your similar tale. You can utilize this to your advantage.

How to stop talking so fast and other bad habits. 


arsejal of anecdotes ita olsen


Be completely relaxed

Social events usually cause quite a bit of tension in our bodies, from the excitement, the anticipation, and the anxiety over the fear of feeling and looking foolish. We all have it. 

Please note that almost everyone at the event feels similarly to you, and most people are too concerned about themselves to be overly observant about what you are doing. So chances are you won’t look foolish no matter what you do. 

You’ll want to keep yourself calm, cool, and collected. If someone upsets you, that means you need to FindYourRelaxedPlace. I can teach you how. Do your Convey Relaxation Exercises until you get to a point where you can rid your body of tension at any given moment.

How to be yourself

What if I’m shy or an introvert?

If you want to have extraordinary networking opportunities, establish fun, productive relationships, and enjoy beautiful conversations with others, you’ll want to do like the extraordinary conversationalists out there and look outward, not inward.

Instead of thinking about how you feel inside, think about how the other person feels inside. It’s quite refreshing. Not at all exhausting. 

When you spend your time wondering if people like you or think you’re smart, you can feel drained. And you just want to go home and go to bed. But when you love your audience, have warmth for the people you’re with, that’s when you feel like you could chat with them all day.

You can mention how you feel at a party where you know no one: “These functions make me feel awkward; I never know what to say to people I don’t know!” The person standing next to you is going to completely relax and say, “Me too!”

Better yet, have anecdotes prepared.

No one was born a perfect communicator. 


improve your conversational artfulness like you would anything else


Speak slowly by using breath groups

Once you are completely relaxed, there will be times during conversations when you want to share your opinion, make a witty observation, or relay a brief anecdote. Leave pauses between breath groups. (A breath group can be anywhere from about 4 to 7 words.) 

Connect your breath groups (linking, don’t drop the ball) but utter them slowly. The same story told twice, once slowly, once quickly, will have two different impacts on the audience. The one told quickly will be confusing and tedious. The one told slowly will leave your audience at the edge of their seats, hanging on your every last word. 

How to not be nervous before a presentation.

Compliment, don’t comment.

You’ll be the desired companion indeed if you give the occasional compliment. C’mon, there has to be something you admire about that person, or you wouldn’t want to connect with them. You can mention a characteristic, “I love your organizational skills!” or just an article of clothing. 

A comment looks more like, “You got your hair cut.” or, “You changed your office around.” Not sure how those are helpful conversational tools.

Here’s how to compliment, don’t comment.

Use influential intonation.

Just like a good song, good conversations have rhythm. So give yourself a few beats before you respond, and make sure you vary the length of your notes just like beautiful music does.

Here’s how:

  1. Vary the volume of the vowels in your sentence.
  2. Emphasize the vowels of the words with a great deal of meaningful content.
  3. Significantly reduce length and volume of all other vowels. There should be approximately a 1 to 7 ratio of “big to small.”

How to improve the sound of your voice.

Really listen to your conversational partner,

A compelling conversationalist will spend most of his or her time listening. People want to be heard. They want to spend time with people who understand them. So listen to people when they speak. Try to understand them. React during appropriate times by letting them know that you hear them.

“I understand what you mean.” “I know the feeling.” “I gotcha.”

It makes people feel good to know that they are understood. Try not to fall into the trap of preparing what you’re going to say next while others speak. You will have the opportunity to talk, and when you do, you will have a firm grasp on your communicative partners’ feelings, preferences, wit, etc., and you will be well-equipped to speak.

If you can master the art of telling quick stories that inspire people to talk and really listening to folks as they do, the more you’ll make people feel warm and fuzzy. So it shouldn’t lead to exhaustion for the introverted.  


online communication training


Be kind.

Use kindness and warmth in your voice. Use warm eye-contact. Even on virtual meetings, make sure you’re looking at the person on the screen.

Don’t use negative phrasing that can lead to miscommunications. For example, don’t ask someone what they didn’t understand about what you said; ask them what you can explain better.

By all means, don’t use the expression, “as I said before.” It’s so insulting!

Also, make sure you’re not working so hard to make people like you and respect you that you become bull-doggish in reporting your narrative.

How to be a persuasive speaker.

Be brief.

Keep your stories/anecdotes short and sweet. Concise and to the point. Good story-tellers practice their tales. They do so during their free time aloud using the recorder. Then they tell the same stories during real-time situations.

An excellent conversationalist’s goal is to get other people talking.

What about questions?

I don’t recommend starting conversations with questions. I advise beginning conversations with concise stories. The following advice applies to exchanges already in progress. 🙂

If someone’s telling you a tale of woe or excitement, really listen and ask questions. When someone’s telling you a story, you may wonder about more details; be sure and ask for them. It goes a long way to make people feel good.


When conversations become boring or trite, segue into something more profound. Simple discussions regarding the weather and everyday activities can end at a brick wall. You can prevent that by considering your emotions as a result of a topic. 

The best communicators understand that humans have feelings that are similar to their own. Know how you feel about something, and you’ll have insight as to how others might feel. Remember that opinions are different from emotions.

Suppose you tell a short story about something mildly embarrassing or scary that happened to you. In that case, your communicative partner will be able to relate to you and will reply, excitedly, with a similar tale of their own.

How to Answer Difficult Questions Like a Genius

Great conversationalists pull together physiology & emotions.

They know they need to be warm, kind, and engaging. That’s where the emotions lie. 

Also, remember the physical aspects: that the more breath groups you use, the better your intonation usage, and the more you listen, the more powerful you are, the better conversationalist you’ll be. 

Anything you’re good at, you’ve worked on.

Improving your conversational artfulness shouldn’t be any different. Since your success is riding on it, it should be even more critical.

Sound amazing in a brave new world.

10 thoughts on “How to Be a Great Conversationalist-Even if You’re Shy”

  1. I’m not sure if I’m shy or am introvert, I must be one of them, but I’m definitely going to try my arsenal of anecdotes!. I never know what to say in the spot, so being prepared is a good idea. Will I have to always practice in advance?

    1. Hey Jin, thanks for your comment and question! No, you won’t always have to practice in advance. YOu’ll want to organize your life in terms of stakes. Low stakes situation (ordering food & beverages or greetings for example) to high stakes situations like being on television or having a job interview. Then you apply these conversational skills tips in that hierarchy, measuring your success all the way through. Of course, in our lives, we have to hire other people to help us accomplish things not in our wheelhouse. I’d recommend you take some sessions with me or take one of our online video sessions.

  2. My stories are always so long! And I never seem to get to the point. Uma try this! I hate recording myself though. I hate hearing my voice on the recorder!

    1. Kris, I hear this all the time! You are part of a large crowd of people who have a difficult time creating stories in their heads. Just know that you have to work on story-telling just like you work on everything else you’re good at in life! But the benefits far outweigh the dilligence.

  3. Very insightful advice. I appreciate this. All over the interweb people are advising the use of questions to start conversations. This just makes more sense! Almost no one wants to be in the hotseat! And I can think back to my recent stories I’ve shared and every time It conjured up something in my friends’ minds that they felt the need to share. Love this, Ita! I’m your newest fan!

    1. Thank you so much, Michael! I really appreciate that!

      I see that, too; all over the interwebs folks are telling people to ask bizarre questions and other generally bad advice. I have to say, it’s what sometimes lights the fire under me to start writing! I get so mad at all the bad advice. I don’t feel like I’m a writer and I’ve needed to increase my comfort level over the past couple of years, but just send me an article with terrible advice and I will write like crazy!

  4. Brittney Pagan

    For me, if I hear people talking about a topic I’m really interested in I would love to join the conversation, but I have to wait for someone to invite me since I’m not sure they would want to talk to me and I would feel like I’m intruding or something (and I’m not good at talking to people I’m not close to)

  5. Siobhan Stewart

    It’s funny, as I was reading these, your tips made me think of the charming, good conversationalists I know. People flock to them, and it often feels like this intangible “presence,” but you’ve shown that there are actually some straightforward steps that you can take to create presence and charm.

    I agree that stories are a great conversation starter, and I like the idea of having a prepped arsenal of anecdotes, so that you aren’t trying to think on the spot.

  6. Ahhhhh… Listening is my challenge when I go for job interviews! I try but inside my brain there’s chaos going on. Even when the interview hasn’t started and they are making small talk with me, I just struggle with listening.

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