How to Be a Better Conversationalist

How to Be a Better Conversationalist

A few months ago, I ran an experiment in talking to strangers. It was difficult at first, but over time I began to notice people who were excellent at having conversations, and others who were more difficult to talk to. Some observations on what makes a good conversationalist I will share here.

Here are seven (subjective) rules on how to be a better conversationalist.

1. Make them feel heard.

The golden rule. You do not have to agree with them or even respect them a whole lot, but you must make your partner feel heard. There are few things more painful and insulting than sharing one’s time and thoughts only to realise that the other person is not listening. They might as well talk to a wall.

The questions you ask will often reveal if you have been paying attention. Take note of any ambiguous details, or any details that have been omitted and gently ask. A great question to ask is, “what do you mean by X?”

Body language is huge here as well. Obvious ways to show you are listening include giving your full attention to your partner (no phones or multitasking) and mirroring (repeat what they have said). Subtler techniques include smiling, nodding and holding strong eye contact – often known as active listening.

However, don’t pretend to listen without really listening. People can usually tell if you are smiling and nodding but secretly haven’t retained a thing. Which brings me to my next point:

2. Remember what they have said.

It is uncommon for people to remember details from past encounters. But if you can make the effort to keep notes from previous conversations and recall them later, you will be rewarded. Remembering achieves two things:

  1. It signals that words are not wasted on you, for you respect their time by listening and remembering.
  2. It shows interest in the other person, and to feel you are interesting is immensely comforting. This may open doors to broader conversations in the future.

Examples of easy details you can remember are:

  • ongoing endeavours (how’s that project going?)
  • family (how’d your sister’s recital go?)
  • pets (how’s your dog?)
  • birthdays / zodiacs / MBTI (isn’t it your birthday next week?)
  • random / quirky stuff (you hate mangoes, don’t you?)

The more specific the memory, the better. “How’s your dog’s injury going? Has he seen the vet?” is better than “How’s your dog?”. But don’t recall too much. There’s a fine line between thoughtful and creepy. I’ll leave you to figure that one out.

Also note that the converse of this statement is true. People that continually forget details you’ve told them are mind-numbingly annoying. If you have to remind someone more than five times that you went to Tasmania last year, or you’ve started a new hobby, or you’re allergic to peanuts, then either they have dementia or they don’t really care. Do not be this person.

3. Use the other person’s name.

Most people – including myself – love to hear their name used. Easy places to add this are in:

  1. Greetings (Hi Tom! / See you later Tom!)
  2. Questions (Tom, don’t you think that bird looks a bit odd?)
  3. Compliments / teasing (Tom, you look dashing today / Tom, your hair is positively filthy)

4. Look excited to see them.

Again, the easiest way to do this is to actually be excited to see them. People can usually tell if you’re faking this. But in case you’re particularly tired, or an alien in need of pointers, here are some quick tips:

  1. Open body language: Stick your feet out towards them. Don’t cross your arms or put hands in your pocket. Lean towards them.
  2. Eye contact: Strong eye contact. Wider eyes show energy and interest.
  3. Vocals: Adopt a slightly higher pitch. Speak faster and louder.
  4. Smile.

5. Share stories (and laugh about them).

If you can tell a personal story and laugh about it, you achieve two things:

  1. You signal that it is safe to be vulnerable. The other person may also take this as an invitation to share some of their own stories, which can lead to more interesting topics.
  2. You give them an opportunity to further drive the conversation. If you’ve told a somewhat decent story, there will be plenty of questions they can ask you, leading you down new paths. Telling stories are a great substitute to a constant stream of question-answer-question-answer.

6. Avoid generic responses.

When responding, try to remove these words from your vocabulary:

  • “Good”
  • “Interesting”
  • “Nice”
  • “Cool”
  • “I see”

99% of people default to these phrases. They are safe and will work in most cases, but they are also boring, show a lack of effort and can often kill a conversation. Alternatives include:

  • “What do you mean?”
  • “Tell me more.”
  • “Why?”

In particular, “why?” is a great question to move onto deeper conversations, as it often reveals deeper morals, values and goals.

Saying nothing is preferable to saying something generic. A short silence can signal that you are contemplating on what’s been said and thinking of a more thoughtful answer than “nice”.

7. Observe, and adjust.

Throughout the span of a conversation you will find topics that particularly strike a nerve. Notice these. If in response to a question they seem uncomfortable and give short replies, it is time to move on. If instead they respond with unusual excitement about a topic, lean into it and remember it for future conversations.

However, in general I have noticed that the topic matters little in how enjoyable a conversation is. If you create a safe, attentive environment, any subject can be interesting. I’ve had fascinating conversations over “mundane topics” like the weather and study, but also easily forgettable ones over “deep topics” like religion, books or mortality. What matters most is the dynamic of the conversations – whether one feels heard, safe and remembered. Bonus marks if you can be a little different and entertaining with your responses (see tip 6).


At the end of the day, feel free to experiment. These tips are only a culmination of my observations and the question of what makes a good conversationalist will depend on your own personality and mood. But if you can make it your chief goal to make a person feel heard, you are most certainly on the right track.

2 thoughts on “How to Be a Better Conversationalist

  1. Hey Eric! I’m glad to see you’re back writing and wanted to say I really love reading your blog 🙂
    I love this post, it reminds me of something I’ve learnt about a lot in the context of psychological therapies, which is that research consistently finds that therapist factors like warmth, relationship building, attentiveness, and connection predict better outcomes more than whatever different content or treatment modality is used. It’s the same principle you observed in personal conversations and I think speaks to how what we need most is just authentic connection!

    1. Hey thanks for stopping by Karuna! Amazing insight – connection is indeed a great starting point in many domains.

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