How To Have Great Conversations - Step By Step
I see a lot of posts asking about how to have conversations, how to go beyond small talk, what should you say or ask about, etc. These were questions that were on my mind often up until my late 20s. I was a shy and anxious on any social situation. In fact, on my late 20s I realised I had never initiated a conversation with someone new, in other words, I had always waited for the other to approach me. This made me feel terrible, but I was in a point in my life that instead of trying to punish myself (as I used to), I decided to do something about it. I had to learn how to approach strangers, have initiative and maintain a conversation. So, if you are in a similar situation, you are probably asking: where to start? You start with basics (that’s what I did) and then you break the problem into small enough steps that you can manage.
I was really bad when I started, I could only say “Hi”, so I began by adding “how are you?”. At that time, I was never the first to ask this question, I would wait for someone else to ask me and I would say “Good. What about you?”. For that reason I started by developing initiative and being the first to ask “How are you?”. For weeks I practised “Hi, how are you?”, until I hit another wall: that was not taking me anywhere. I didn’t know what to say after that (you might relate to that), and I felt something was missing. What I was missing was a genuine authentic connection. You might feel there is a need inside you that you name as a “need for talking” or a “need to have a conversation”, but it is really a need for connection, a deep, authentic, truthful connection. So how can we go about having such connection? We need to ask better questions, share things about ourselves and change our attitude.
Let’s start with better questions. I defined a rule or myself: get beyond small talk using a maximum of 2 questions. So after the “how are you”, I started trying to only use 2 questions to get to something meaningful. The attitude you need to embody is of genuine curiosity for other people, it’s all about discovering what makes the other person tick. Stay away from just interviewing the other person or just discovering facts about someone, try to discover the emotional involvement of the other with the thing you are asking about. I will give a few examples:
Question 1: What are you studying? (This is discovering a fact.)
Question 2: Are you enjoying it so far? (This is discovering how the person feels about it)
Another example:
Question 1: What do you do in your spare time? (Again, a fact.)
Answer 1: I like listening to music. (Here the temptation is asking more facts like “what sort of music?”, “do you like this or that?”, which are valid questions but try to use a different approach.)
Question 2: What is it about music that resonates deeply with you?
Or: Why is music so important for you?
Pay attention to the alternatives. Can you see the difference between the interview approach and the genuine interest approach?
Now, even using this approach there is the risk that you might turn it into an interview. Yes, you start asking better questions, so it is a better interview but there is something missing: your own openness. So far, you are just asking, you are just taking, taking, taking… This causes the other person to not feel comfortable and might not want to show more, might not want to go deeper. The other person might find it difficult to trust you. So, what do you need to do? You need to start giving, you need to open up.
If you are talking with someone that is good at having conversations, they will ask you questions too, so you need to show openness and willingness to go deep. If not, you need to be the one sharing even if you are not asked to. Example:
Question 1: What do you do in your spare time?
Answer 1: I like listening to music.
Share 1: I love music too. (That’s fine but go deeper) I listen to rock and jazz. (still shallow) Music has always been part of my life. (better) I like to feel the energy of music, it’s like there is always a song that could be the soundtrack for a situation in our life. (good, keep going) Music helps me connect and understand my emotions better. (Now you are starting to get there)
You see, there is no limit to how deep you can go, it’s up to you. The difference is that with this approach you are starting to dictate the pace, you are controlling how deep the conversation goes, and therefore how deep the connection.
Now you might think that you need to slow it down. If so, slow it down. You might think “what if it is too much?”, that’s fine too. One of the best ways to go about it is to call it out. Let’s say you are going too fast and you just asked something that is very private too soon. Here is what you do:
Call it out 1: “I’m going a bit too fast, no? I see it now, it’s just that I am curious about you and your story.”
Call it out 2: “Is this too much of a private question? I didn’t mean to be too intrusive.”
Call it out 3: “I think I ask too much again. This really tends to happen to me, I get too excited some times.”
Addressing it will make the other person know that you are aware of what you are doing, it just so happens that you are interested and curious. Many times, the other person will end up going deeper because you are showing you are calibrated. Other times, you need to take the lead and change subjects, which is perfectly fine.
Last questions I want to suggest. Do not be afraid of jumping to the cold water. What I mean is: do not be afraid of going deep fast. Use questions like:
Question 1: What is your biggest dream?
Question 2: What are you most afraid of?
Question 3: What is the one thing that you really want to do before you die?
Remember, if it is too much, you can handle it by calling out the intensity of the question. Do not worry, do your best to relax as much as possible, and more importantly be ready to answer these questions yourself.
The very last thing I need to mention, it’s “the secret” to a good conversation: silence. Know when to talk and when to stay in silence. Listen well and develop the ability to stay in silence even when the other is not talking, even when it is creating pressure, when it’s a little bit awkward. Sometimes the only thing we need is space, so we can talk. That space is created by silence, so learn when to use it, it’s more important than words.
I hope these suggestions and this way of thinking about conversations can help you and serve you as a guidelines. Conversations are about words, silences and attitudes. Let all these elements flow naturally through your personality, so do not copy me or others word by word, make it your own. Create your own way of having conversations with these elements and express yourself truthfully. It might seem a lot but I am sure you are able to have great meaningful conversations.
All the best!
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How To Have Great Conversations – Step-By-Step