Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

How to Increase Your Conversational Skills

Dear David,

How do you make and keep friends when you are inept in conversation? I can be in a crowded room, sit in one corner and just people watch because I have nothing to say. Also, if I have an opportunity to go out to places where there will be more than two people, I find every excuse not to go. Sometimes I manage to push myself out the door, but rarely. Any ideas?

A Couch Potato (in front of a computer)

Dear Couch Potato,

I can certainly say, “been there, done that!” I was painfully shy and socially inept well in to my thirties. Some would say I remain pretty socially inept. I guess my own situation explains in part why I chose to dive deeply into the study of psychology.

While in graduate school at Stanford, I volunteered at a Shyness Clinic that Phil Zimbardo was running as a part of his research. He eventually wrote an excellent book, Shyness: What It Is, What To Do About It. I recommend checking it out.

Before I began working with Phil, I had assumed most shyness was due to poor social skills. But it turned out I was wrong. The shy people we studied were actually quite skilled. The problem was they were also harsh self-critics and were extra-sensitive to social rejection. It turns out most of us fumble and stumble our way through social situations; and shy people notice their slip-ups more than the rest of us.

What helped these people the most was to practice conversations, warts and all, until they realized their fumbles weren’t any worse than anyone else’s. Of course, this practice also helped them improve their conversation skills. With that in mind, I’ll suggest a couple of ideas for practice.

Conversational Tennis. This game comes from my dear friend, Al Switzler. I’ve used it myself, and with many of my nieces and nephews. You play it with one or two other people, perhaps on a car trip or during a meal. Here is the setup: The goal is to keep the conversation going. One person begins by serving a topic across the net. The other person’s goal is to respond to the topic in a way that sends it back across the net, and keeps the conversation going. See how long you can keep the topic in the air. After a while, it will be the other person’s turn to serve up his or her own topic.

This game works well to practice keeping conversations alive. I find it’s really fun with teens who are used to responding in monosyllabic grunts and nods. They quickly see what it takes to participate in a conversation.

Topics to Discuss. You can find several websites that suggest conversation starters. And there is some excellent research on how the topics of conversations flow among strangers and friends. The basic finding is that we begin by talking about very broad and noncontroversial topics, such as the weather, traffic, or jobs. These are easy topics for others to hit back across the net. We use them to keep the conversation going while we listen for common interests and other, more personal, connections.

As we begin to feel safer with the person, we reveal more about ourselves. We test how safe and rewarding it is to disclose our interests, our hopes, and our fears. This phase of the conversation is a bit like a dance. Disclose too much too soon, or ask questions that are too personal too soon, and your partner will feel uncomfortable. Keep the conversation on surface topics for too long, and the person will think you don’t want a personal relationship.

The researcher, Arthur Aron, has studied this process in the lab, by giving strangers a series of questions to discuss with each other. The questions begin at a surface level but become increasingly personal over the forty-five minutes of the experiment. Because of the situation, people feel fairly safe with each other. As the questions become more personal, they often find themselves disclosing information they’ve never shared with anyone before. When they see the way their partner reacts to their revelations, they develop trust, liking, and even affection for them. In fact, these questions have developed the reputation as “The 36 Questions to Fall in Love.”

Rules of Improv. Where should you start? I suggest you begin with low-stakes conversations—perhaps with phone calls with family members. I don’t know about you, but I try to call my mom every day. Use conversations like these to test out topics that work for you. In addition, follow the First Rule of Improv: “Always AGREE, and SAY YES!” This rule doesn’t mean you should “agree” or “say yes” to everything your conversational partner says. Instead, it means you should respect what they’ve said, and hit the topic back to them in a way that is safe and easy for them to respond to. The rule is another take on conversational tennis.

I hope these ideas will be helpful. Now turn off your computer and call your mom.

Best Wishes,

Develop Your Crucial Skills

Image for

What's Your Style Under Stress?

Discover your dialogue strengths and weaknesses with this short assessment.

Take Assessment

Image for

Subscribe Now

Subscribe to the newsletter and get our best insights and tips every Wednesday.


Image for

Ask a Question

From stubborn habits to difficult people to monumental changes, we can help.

Ask a Question

21 thoughts on “How to Increase Your Conversational Skills”

  1. Dave Birren

    This is great! As a dedicated introvert and social nerd, I see myself in Couch Potato only too clearly. David, your feedback is excellent. However, I think it misses a crucial point.

    We must be interested in others before we can have a real conversation. Small talk is one thing, and it’s cheap. Real conversation draws another person out, and it can’t happen if we’re caught up in our own self-interest, self-consciousness, or shyness, which is a form of self-consciousness.

    After many years of difficult and awkward social encounters, I decided to take an analytical view of parties. I listened to conversations and noted their depth – the weather, the job, the kids, etc. I learned what people like to talk about and persuaded myself that it matters. In time, I developed an interest in what others are interested in and conversation became much easier.

    In short, when it’s about me I clam up. When it’s about the other person I have no end of questions.

    And you know what happens when you get people to talk about themselves, don’t you? They like you.

    Now … would you care to share with me some of the experiences that brought you to this line of work?


    1. Julinda

      Excellent comment, Dave!

      1. Dave Birren

        Thanks, Julinda. 🙂

    2. David Maxfield

      Thanks Dave, these are excellent additions. I see two insights: First, when you focus on the other person, you become less self-conscious. Second, we all need to cultivate our interest in other people.
      When I was in elementary school, nothing was more interesting to me than the wild creatures that lived around us in the swamps of Florida. I spent untold hours hidden in make-shift blinds watching snakes and owls and possums. My dream was to become a biologist, who could watch animals all day.
      As it turned out I became a psychologist, and I get to observe the most fascinating animals of all–humans. Aren’t humans wonderfully complex and just wonderful?

      1. Dave Birren

        Thanks, David, and you’re welcome. I was going to be a concert pianist but I ended up a management consultant. Over time I developed a similar attitude as yours about humans as complex and interesting. What has really helped me is to see each person as the center of the universe; i.e., his or her own universe. When we fail to acknowledge that we forgo the ability to get their attention. The ego never sleeps.

  2. Alane Howerton

    Thanks Dave.

  3. Joshua Knight

    Thank God for your, David Maxfield, and for you, Crucial Conversations. I have Unsubscribed from so many emails due to my very very little amount of time in the day. However, I have always found joy and hope and real good advice in almost all of your emails. David, this Shyness article is absolutely on par and even above so to push me to write a review about how beneficial I find this piece every week. Please continue this work and thank you! I hope you keep track of all that have read your articles, even if we don’t have time to espond or comment. Also, it would be good to add a simple ‘Like’ icon to the article, so we can simply, easily,without further ‘clicks’ and DEFINITELY without any signing in say that we like the article you just sent us.
    Thanks again!
    Sincerely, Joshua Knight

  4. Kate Hayward

    For a really great look at improv tools, I can’t recommend Patricia Madsen’s book highly enough.

    She’s up there with you guys.

  5. Julinda

    I read that book by Philip Zimbardo as a teenager! I didn’t get over being sh,y but it helped me understand it a lot more. I’m 54 now, and while I’m still an introvert and socially insecure, I can small-talk with the best of them. What helped me was (1) being around people (at work, etc.), (2) realizing everyone makes pointless, silly, and sometimes stupid comments at times (I mean, the weather? How many times do you hear, “Sure is hot today” on a hot day?), so I don’t have to be embarrassed when I do, and (3) just doing it. As David said, start with low-stakes conversations – simple topics with nonthreatening people. And listen! Sometimes if I’m nervous I have a tendency to think too much about myself and what I’m going to say.

    1. Julinda

      In spite of being good at small talk now, I still share Couch Potato’s problem of not being able to make friends. I can’t take social interaction to the next level of a deeper connection, because I have this “They wouldn’t want to be friends with ME” feeling. Any ideas to help with that?

      1. Jayne Nielsen

        Julinda. When I read your statement, I read “not being able to…”, I can’t…”, and “they wouldn’t want….” These are all negative statements. Maybe it could be all that [negative] energy that is hindering or hampering your ability to “make friends”. My suggestion….find a passion and located activities or organizations that match that passion. Seek out doing greater good for others, which will take the focus off of you and your needs. You may then find there are people who will want “to be friends” with you.

        1. Julinda

          Right, I have low self-esteem which makes me feel like I’m not good enough. Even though I’m successful in my career, active in the community, and have a good marriage and kids, I still have that lingering self-doubt.

          1. Jayne Nielsen

            Congratulations, Julinda. It sounds like you are on the right track. However, having and doing all these things are good but there is one thing I think you’re lacking (other than self-esteem) and it’s PASSION.

            You may be successful in your job and enjoy being active in your community. And you obviously love your family but you haven’t found YOUR PASSION.

            To find what your passion is, John Maxwell suggests finding what you love to do that you would do FOR FREE, build those skills, and become an expert in that field.

            For example, I rescue German shepherds. My passion other than saving their lives is to take unruly ragamuffins, rehabilitate and train them, and find homes for them. Once I retire that’s what I am going to do…for free.

            Stephen Covey refers to an emotional bank account. I think you’re spending more and not depositing enough into yours. Once you find and pursue your passion, I can guarantee you’ll find your emotional bank account overflowing and not being overdrawn.

            Overwhelm the negatives with positives!!!!

      2. Dave Birren

        Julinda, in my view the issue is weak self-esteem, the quality that says, “I’m not (good) enough.” Do whatever you can to heal the wounds where that comes from, and then banish it from your vocabulary and your life. The work of Brene Brown is useful, at least as a starting point.

        1. Julinda

          Low self-esteem is definitely a big part of it. In some situations I’m confident and sure of myself, but when it comes to making friends, I feel unworthy! I have heard of Brene Brown but not read anything – I will check it out. Another problem I have is that I had my kids rather late, so when it comes to activities where I’m around other parents, I’m old enough to be mother of many of them! So that adds another factor to the “they won’t want me” feeling.

          1. Jayne Nielsen

            Since you’re still working, you must be about my age or you’re younger than I am (I’m 53 and proud of it). Being older then many of the other mothers isn’t a negative at all. Being older gives you the opportunity to share your wisdom, knowledge, and life experience with them. But don’t try to “keep up with the Joneses”. And don’t try to be someone you’re not. And most of all, don’t try too hard to be liked. Stay genuine. Remain sincere. That’s what people like and that’s what people are drawn to. Also, have you thought about embarking on a workout program? Getting into shape and building some muscle are great self-esteem builders.

    2. Jayne Nielsen

      To begin “small talk” I find one thing that a person a wearing (jewelry, article of clothing, etc.) and I comment on that and then the questions start flowing. Just doing that opens the door to broader topics. Also, every time I am in line at a store I refer to every clerk, salesperson, etc. by their name (I look at their name badge). I ask them how they are doing and how their day is going….and the conversation begins. It’s not hard. I have learned you have to take the focus off of yourself and put the other person in YOUR center of attention.

  6. Clifford Spoonemore

    Thanks, as an introvert it is hard to keep the tennis ball in the air. We start a conversation on a safe topic that may have come from the last session of a conference. Then the ball is dropped (end of the topic). The choice is either to leave or to try and find another topic. That is the hard part for me, finding the second or third topic. I know the person I’m talking with does not want to be talking with me all day/night. As we play the conversation game of tennis and get better at it I may find the spot that it is okay to shift tennis courts without just walking away at the end of a really long pause after the first topic is over.

    1. Dave Birren

      I get that. Being single, I’ve spent quite quite a bit of time in the online dating world. I’ve learned to spot the moment on the first (and usually only) date when we’ve been together long enough. During a lull in conversation, if a good question doesn’t arise, especially after an hour or so of good interplay, I ask, “Is this a good time to break?” or “Do you think we should come back to this later?” The responses I’ve gotten have ranged from a look of relief to a deepening of the conversation.

      The key thing is to recognize that all conversations come to a close. As an introvert, you’re probably fairly perceptive. Pay attention and see if you can notice the moment when the door is closing. You know what happens when you try to hold it open – your fingers get pinched.


      1. Dave Birren

        I forgot to mention – the key to this is keeping your shared purpose in mind. Are you (both) interested in the content of the conversation, as well as related topics that might come up? Do you want to get to know the other person better (and is it mutual)? Are you just passing the time? Be sensitive to goal conflicts. As the song goes, “I thought that you’d want what I’d want. Sorry, my dear. Send in the clowns.”


        1. Clifford Spoonemore

          Thanks for the comments: it is yes and no of course. If with a male colleague: it maybe more to pass the time during a conference or meeting. Possibly sharing a few small life stories but nothing to deep. If it is a female co-worker it is trying not to cross that line of when did we get past small talk. For me, I’m married, I don’t want to cross that line. It is a big bold line in my view so I don’t want to get that close to it. When you are at a 2-3 day conference then the tennis court has many opening serves, but if you do just want to talk about the weather topics then you need to know a bit more about this game of conversation.

Leave a Reply

Get your copies
The ideas and insights expressed on Crucial Skills hail from five New York Times bestsellers.


Take advantage of our free, award-winning newsletter—delivered straight to your inbox