Learn how to start conversations
May 2023 | The Learning and Wellbeing Team

Learning how to start a conversation and keep it going is not something that you learn in school. In fact, it’s something that many of us never learn or master as well as we would like. Still, some people just seem to be so very natural at it. They can talk to anyone in a way that seems effortless.
For most people, having conversations is hard work, that most people would like to learn how to do better. Not surprisingly, there are hundreds and hundreds of self-help books on how to talk to people. The first book on how to have conversations was published in 1936 by Dale Carnegie. How to win friends and influence people was an immediate best-seller in 1936 and to this day continues to do well, selling over 30 million copies. A survey conducted by the Library of Congress in 2013 ranked it as the seventh most influential book in American history.

Conversations can be broken down into three parts, ask, listen and tell. Take a moment and observe two people talking. If they know each other well, there’s usually a seamless transition from one topic to the next. It is really remarkable how it all works. Good friends can transition from one topic to the next, which at times seems to have no reason or logic. Let’s take a look at each of them in detail.

Asking questions is a key element of all conversations. When we see someone either for the first time or after a long time, we usually ask them how you have been or how they are you doing. If you’re getting to know someone for the first time, you may ask them how long they have lived in Ottawa. How long have you been at the university or at (your workplace)?
At some point, there’s usually an ask of some kind. It might be an ask with respect to information (e.g., how are you?). It might be an ask for help. Or it might be an ask for a date, a job or a meeting. Sometimes, an ask is how you can show interest in what the other persons talking about.

Tip: Spend some time listening to other people talk. You can usually find these three elements.

Nonverbal invitations

Conversations go better if you look approachable. It’s easy. Just smile. If you are ever in doubt about how powerful a smile is, just walk down the street smiling and count the number of people who say hello or smile back. If you don’t look approachable, it is far less likely that people will talk to you.

Give it a try.


Listening is essential to all good conversations. Listening insurers that the person you are speaking with has enough time to tell you something that is important to them. What they tell you may not seem important. We all know some people who can go on and on and on about seemingly unimportant details and trivia. People can go on and on for a number of different reasons. They may be truly interested in every fact and statistic about baseball. Or they may be very anxious and default to talking about what they know best. Either way, it’s important to them. Listening to them, even if it is uninteresting to you, is part of being a great conversationalist.

Listening can be broken down into two types, active listing and passive listening. Passive listing involves paying close attention, maintaining eye contact and being patient. We all know someone who has told the same story over and over again. Active listening involves that you are paying attention what that other person is telling you is interesting, and that you would like to hear more. You can acknowledge your interest in a single word (e.g., “wow”), several words (e.g., “that really happened?”), or even by asking a question about the person talking to you (e.g., “what was that like for you?”). All of these remarks communicate you are interested attention. It can be hard, especially when you have something you’d like to say or when it’s not exactly something you’d like to hear.

But that’s part of the deal in a conversation – taking turns.

Tip: Conversation is a skill. Not everyone is good at this, but everyone can get better.


The last part is that tell. Telling people about yourself, about your day, or about your interests is equally important to developing a good conversation and, over the long term, developing new friends and allies. However, this part needs to be balanced with the other two elements of the conversation. We all know people who have mastered this part of the conversation and nothing else. That’s the person who can go on and on and on, whether it’s about themselves or about a topic that interests them. These are the people who don’t know when to stop, can’t read the room, and very quickly can become irritating and boring.

What’s your openner?

All conversations start with an opener. It’s how people get conversations rolling. They can start with an ask (e.g., how’s your day going?) Or they can start with a tell (e.g., I can’t wait till this week’s over; I’ve got this one prof that’s buried me in work; did you see the game last night). It doesn’t matter how you start. Either an ask or a tell is a good way to go. However, you may need to try out a number of different things (see the four types shared above).

What’s your conversation style?

The Communication Styles Questionnaire is comprised of 92 questions assessing 23 different communication styles. This is one of the longest questionnaires on the website (it takes about 15 to 20 minutes), but it may be worth a thorough, in-depth dive into your conversational style. 

Here are a few of the 23 styles that are assessed:  

  • Talkativeness
  • Conversational dominance
  • Humour
  • Verbal aggressiveness
  • Unconventionality
  • Inquisitiveness
  • Argumentativeness
  • Worrisomeness
  • Tension
  • Defensiveness
  • Ingratiation
  • Charm
  • Concealingness

After completing the questionnaire, you will be provided with total scores on each of the 23 different communication styles. Then it is up to you to think about how you might want to change your conversational style. Maybe it is time to be a little less dominating and defensive and a little bit more inquisitive or talkative. 

The crucial role of small talk and chit-chat

For a very long-time, chit-chat was seen as a waste of time. Many people would proudly state that they don’t do small talk, that they can’t do small talk. More recently, researchers have begun to understand the essential rule that chit-chat plays in small talk, our daily lives and our society as a whole.

One study showed that individuals who more naturally and more frequently participated in small talk and chit-chat reported higher levels of well-being at the end of the day.

What should I say?

In this part of the conversation, you get to tell the person you are talking to something about yourself, what you like to do, what makes you interesting, a good friend to have, a good ally or a good hire. It can be a chance to vent about your day or an opportunity to garner some interest.  

With new friends or acquaintances, you don’t want to share too much too soon because that can be overwhelming. And you shouldn’t share information that’s too personal or too polarizing if it’s a conversation with someone at your workplace or prospective employer.

Here are four types of shares.

When you have a chance, take a moment and listen to the conversations of others. See how they transition from ask to listen to tell. And see what kinds of “shares” happen. Typically, there are four different classes of shares.

1. Facts: Did you hear about this? Check this out.
People will often share facts about something. They send each other videos and memes or share some kind of fact about some event or of something that is of interest to them. It is a good way to start. Most people will usually say something in response and usually follow up with a tell of their own. There are two things to watch out for. If you go on and on with the facts, don’t ask how the other is doing, listen and acknowledge what the other is doing, then you will quickly become boring for the other person.

#2. Self-disclosure. Self-disclosure involves telling other people something about yourself. It can be something you are interested in doing, or it can be something that you struggle with. In every instance of self-disclosure, you are revealing something about yourself. Most people are interested in people — what they struggle with, what they worry about and what they hope to be.

Disclosing how you are doing or what you are feeling opens you up to others. It is an instance of vulnerability in that the other person knows something about you. It is an important exchange of information, which allows others to evaluate if you are a threat to them, and if you are an interest to them. Sharing your feelings about yourself is not easy, but it is the currency of meaningful conversations that go beyond sharing facts and the currency of forming the most meaningful friendships and relationships.

There are three types of self-disclosure, each of which is essential to fostering the conversation. People respond more to solving this closure, and they are generally more interested in people. Self-disclosure is the best way to assure others that you are approachable, non-threatening, and interesting.

2.1 Self-disclosure #1: I’m looking forward to …
This first type of self-disclosure simply communicates an interest that you have. For example, you might just say that you’re looking forward to the weekend. You’re going hiking, relaxing, reading a book or going out to a new restaurant that you haven’t been to before.

This type of self-disclosure shares something about you that isn’t too private but may be of interest to others. For this type of self-disclosure, you do need interesting things to share. You can improve this aspect of conversation by pursuing a range of interests that make you a better person. It doesn’t matter what it is, but you do need a number of things to do. You may decide that you would like to have more interesting things to share, which means undertaking some new activities are returning to some old hobbies.

2.2 Self-disclosure #2: This has been such a tough week …
This second type of self-disclosure involves more private information about you. For example, you might share it’s been a tough week, that something didn’t go as well as you had hoped, or that you were worried about an exam, but it went OK.

This type of self-disclosure shares something that is private. In doing so, you’re letting people know that you, like most other people have difficult weeks. That will make you more approachable, but it does make you vulnerable to what others may think of the fact that you worry. But that is precisely why this type of self-disclosure is so important. It opens you up and builds trust. The biggest barrier to this kind of self-disclosure is usually your worry about what other people might think about you. You can’t really know what others think. And what matters most is how comfortable you are with yourself.

2.3. Self-disclosure #3: I felt so humiliated …
This third type of self-disclosure is the most intimate, and it should be shared only with those that you trust. And only those that you know very well. For example, you might tell someone exam you answered a question incorrectly in class and felt like an idiot.

This type of self-disclosure shares something that is very private about yourself. In sharing this information with someone else, you communicate that you’re trusting them with feelings that may be painful. However, because this information is hurtful and embarrassing, it should be shared rarely and only with people you trust. People that you don’t know well or who are competitive or mean will use this kind of information against you. They may spread rumours; they may tell others.


Steven Watts, Self-Help Messiah (New York: Other, 2013) 2–4.

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