4 Hidden Ways To Have Deeper Conversations

4 Hidden Ways To Have Deeper Conversations

TLDR: Ever had a deep conversation when time flew by and you connected wholeheartedly with your confidante? Oddly, time froze and you were fully present. How can we create conditions for such conversations to occur?

The Challenge:

Alas, why is a heartfelt conversation hard in the first place? These days, our attention span has been altered crazily by social media. Instagram Reels & Tik Tok reward our brains with shots of dopamine whenever we get a comment or like. Groovy music or snappy videos serve us a fresh shot every day.

It is no wonder a deep conversation is hard to come by — a social treasure waiting to be discovered. We can learn to steer conversations deeper rather than staring at our screens.

Here are four subtle ways to create deeper conversations within your social circles or even Dhamma youth groups! These are methods borrowed from people wiser than me!

1. Ask Better Questions

We were taught to avoid the ‘weather talk’, to avoid politics, and religion (sharing Dhamma anyone?). Does this mean we talk about neutral and bland topics?

Tim Ferris, an American entrepreneur who does awesome podcasts about self-growth, begs to differ. He interviews people from all walks of life and asks them deep questions that seem superficial.

Those simple questions lead to deep lessons and conversations with the individual. Questions like ‘How has a failure, or apparent failure, set you up for later success? Do you have a favourite failure’ of yours?’ or ‘In the last five years, what new belief, behaviour, or habit has most improved your life?’ or ‘What is the book (or books) you’ve given most as a gift, and why?’

Why are these questions ‘better’? 

These questions are not too broad (e.g. ‘how are you doing?’), which makes the speaker reach out for an equally broad answer like ‘Been busy’ or ‘Been fine’. They are also not too piercingly direct, which erodes the conversation’s psychological safety (e.g. ‘How has your marriage failure affected you?’). 

Tim’s questions give guardrails for the speaker to reply and also the space to steer the question into comfortable grounds. 

This process boils down to the quality of empathy – the ability to think from that person’s perspective and find a middle ground question that makes them feel safe and open. 

Tying these questions to the person’s most recent happenings can help you add flavour to your soup of questions. Context matters! For example, if it is a festive season such as Vesak Day or Christmas, you might want to phrase the ‘book’ question (mentioned above) as ‘Oh Vesak/Christmas is coming up. What books would you recommend giving people in the spirit of this giving season?’

Contextualising our questions nudges us towards having a true interest in the other and avoids the ‘risk’ of creating a checklist conversation.  

2. Make writers, not witnesses

It is never about what happened to anyone we speak to. How they experience their lives is what makes the conversation insightful. Asking better questions is just one part of the puzzle; making your speakers do more than a recitation of their week is another.

Use open-ended questions like ‘How was it like to be the first…’ or ‘How did you manage to cope with…’ to keep the conversation centred on your speaker. Follow up on their stories by asking your friends or family members about their perspective of the event in retrospect. 

This conversation technique gives the person an opportunity to add a new layer of emotion and even transform that pain into a lesson of wisdom and love. The conversation then allows them to write and rewrite their experiences.

3. Don’t fear pauses

If we are listening to respond rather than to understand our speakers, we can be afraid of silent pauses. Pauses can be dreadful in a conversation where we talk to impress. When we are unable to elucidate a response at that moment, we fear that we may have just said junk.

If we perceive pauses as mindful breaks to settle back in the present moment, we give ourselves time to internalise what has been discussed. 

There is no rush. There is nowhere else to be.

What can help us through pauses, is to dig deeper into what has been discussed. One can use phrases like ‘Oh yes, you mention that xxx means xxx for you. What brings you to that conclusion?’.

These questions help to replace our fear of pauses with curiosity about a person’s stance on different topics. Our focus shifts from ‘I have to say something smart’ to ‘Oh wow, what led this person to think this way’. When we have that level of curiosity, our fear of silence diminishes. 

4. Smile at disagreements

The opposite of silence, some might argue, is disagreement. People can disagree on topics that are personal to you. The other may say Buddhists are just ‘idol worshippers‘ or ‘Meditation is useless’. What do you do?

That is where the mindfulness & metta practice gets into play. We acknowledge that there is a disagreement and then find ways to understand how that person arrived at his/her/their evaluation. 

Remember, once you see yourself or your identity as under attack, you arrive at suffering-land.

Hence, it is critical to remain calm when your opinions are challenged. It is okay to say ‘I am not comfortable discussing that right now’ rather than to engage in a battle of shouting views.

Adar Cohen, a renowned mediator, brings the term ‘gem-statements’ into the art of conversation. When both parties have done their best to listen and be empathetic, someone unearths the priceless gem. It is usually one to two short and powerful statements. The statements should be a genuine expression of your feelings and have a strong, positive, and meaningful impact on the other person.

These are some gem-statements that you can bring to your next ‘disagreement’:

‘We kept on fighting because none of us is willing to walk away from this friendship. That’s something.’

‘Even when we can’t agree on how to take care (of your) uncle’s health, I’ve never doubted your good intentions. I know you want the best for him’

This gem-statement lights the way around a compromise or towards a solution.

Deeper Conversations ahead!

There are way more subtle ways to have deeper conversations than the four tips highlighted here. However, grasping these four methods right will help you to get started in becoming a subtly deep conversationalist. May you find that deep moment of clarity and precious insights in your next conversations.

Wise steps:

  • Better questions are crucial in starting conversations, memorise some of them and try them next time

  • Remember ‘Writers & not witnesses’, get someone to share their emotions and experiences and not the key points of their event

  • Don’t be afraid of pauses in your conversations. Treat them as a mindful pause to recollect and refill your empathy jar

  • Find gem-statements, one to two empathetic and impactful lines, in difficult conversations. Be ready to walk away if it is too much!
How Looking At Kopi Cups Can Make You A Better Listener

How Looking At Kopi Cups Can Make You A Better Listener

TLDR: Active listening has become rare in the social media world. Being genuinely curious and asking the right questions can make you a better listener. How to know if you are becoming a better one? Kopi cups will be your guide!

Met someone that can’t stop talking about themselves? Or, heard about how similar your issues are to that person’s and that “you can get through tough times, just like them.“?

It is not a pleasant experience; someone is deaf to what you are saying. Hearing the reply “my dad also passed away recently too” to your sharing of loss is cold comfort. As cold as a kopi you forgot about after making it. It ain’t pleasant. 

We are sometimes guilty of being the inactive listener and other times, the receiving end of it.

How can looking at Kopi cups tell you if you are becoming a better listener? Before we get there, we have to understand what is active listening and how to get better at it.

Active Listening: What is It? 

Active listening often refers to a way of listening that keeps you engaged in the conversation positively.

It requires listening attentively while someone speaks and reflecting on what is said, without jumping into advice and judgment.

Put simply, it has two main components:

  1. Shutting up to listen and not give advice
  2. Recognising you don’t know everything about the person

Naomi Henderson, the suffragist, summarises:

“The real secret to listening I’ve learned is that it’s not about me…I’m holding my cup out in front of me. I want to fill my cup and not pour anything in their cup”

Active Listening: What It is Not 

It’s easy to get complacent about how well we know our friends. It is hard not to make assumptions about strangers based on stereotypes.

Assumptions quickly become our earplugs. It makes us inactive listeners as we listen through a stained filter.

Kate Murphy, the author of ‘You’re Not Listening’, argues that listening has become a scarce skill in the age of social media. Social media is not designed for how real communication works. We do not show friends a picture of our Laksa before asking them a question. The extreme focus of broadcasting ourselves has made us deaf to what others say and need. 

So…am I an inactive listener?

If you answer “Yes” at least once, you might be having a cupful of inactive listening episodes.

Listening Audit:

Recently, have you found yourself saying…

  1. I feel you, I also….
  2. Oh wait, we aren’t talking about X already? Whoops, sorry I am blur
  3. I think that you should… (replying with solutions instead of empathy)
  4. I hear you BUT…
  5. Don’t you think that (inserts your assumption)

Now that you have done an honest audit, what are the benefits of listening?

Why Listen?

1. It makes you stand out positively

“If you want to really stand out in today’s world, stop talking about yourself and learn to hear what others are saying.” Kate Murphy.

It shows to people that you truly care, something rare today. A 2018 survey found that 46% of Americans said they did not have meaningful in-person social interactions.

How does being more outstanding look like?

“When I left the dining room after sitting next to Gladstone, I thought he was the cleverest man in England. But when I sat next to Disraeli, I left feeling that I was the cleverest woman.” Jennie Jerome (Winston Churchill’s mother)

Jennie spent an evening with two politicians. Disraeli stood out. Disraeli spent the evening asking questions and listening attentively to her responses.

He wanted to know everything about her and steered the conversation consciously towards her.

Naturally, Jennie felt good talking about herself. (Just like everyone else). Disraeli, who stood out amongst his peers through active listening, became the future PM of the UK while Gladstone handsomely lost the contest.

2. It helps you empathise better in a noisy world

With deep listening, we give our attention and energy to others. To listen is to let go of the self and be fully present for others, even when they are expressing strong feelings. 

If we want to help a friend who is suffering, the best we can do is give them space. Space to share, cry and think.

When someone asked the Buddha for help or questions he did not say “That’s what happened to me before I became enlightened, it’s annoying yea?” He sat and heard what they needed to say and did not respond until they had finished. 

Buddha was always uber busy attending to monks, nuns, kings, and merchants. However, if he could sit patiently and listen to questions, we have little excuse to not strive to achieve a small cupful of his empathy. 

(Fun fact: Buddha was a busy person who slept at 2 am and woke up at 4 am to start teaching for 45 years)

In a world where there are noisy broadcasts of self-promotion, we can swim against the stream. We can empathise and listen.

2 Ways We Can Be Better At Listening. 

1. Be curious about people

PM Disraeli had a strong curiosity about people. Before engaging in your next conversation, come up with a list of questions to train your curiosity muscles.

You can kopi-cat (copycat) Tim Feriss’ questions. A renowned writer, Tim asks his interviewees questions like: “In the last five years, what new belief, behaviour, or habit has most improved your life?”. 

Notice how it focuses strongly on the individual and not on random news/topics?

If this is too much to try with strangers, try it with close relatives or friends. You may get to know them deeper than before. Keep your focus on asking people about themselves. You don’t have to say a lot.

You just need to be asking the right questions.

Armed with the questions, ensure that your questions are an invitation to a conversation and not a question checklist to be completed.

2. Ask the right questions

Having built curiosity about everyone you meet, how can we ask the right questions? Charles Deber says there are two responses we can offer in every conversation. Here are two examples of Shift vs Support responses.

While ‘shift’ responses make you feel that you are connecting with their situation, it doesn’t help the other person feel better. 

In the case of your friend not feeling well, we’d respond with sympathy and ask a question. You might try asking what they are planning to do now.

The key to getting these right is to ask questions that get people to explain their situation in greater detail.

You might try a follow-up about a specific aspect that you don’t understand or want to know more about.

How Do We Know We Are Improving As Listeners?

The Kopi Test:

The next time you are eating with friends who eat at a normal pace, try this. If your cup is first to empty and you didn’t rush your meal, you are most probably listening. When you are busy drinking, you have more time to listen.

If your kopi cup is full while everyone’s cup is empty, try harder next time to listen more.


The second way is straightforward. When someone tells you are a great listener. That’s better than looking at kopi cups. The feeling of connection after a good conversation and the genuine smiles exchanged is a great testament to your listening skills.

May the next time your eyes catch a kopi cup remind you to listen more and talk less. *sips*

Wise Steps:

  • Look at kopi cups to see if you finished slower than your friends, it may mean you need to improve on your listening
  • Be genuinely curious about people, ask them for more details of their lives
  • Focus on ‘support’ responses and reduce ‘shift’ responses, it is a gamechanger
Toxic Positivity: When Always Looking On The Bright Side Is Harmful

Toxic Positivity: When Always Looking On The Bright Side Is Harmful

TLDR: Burying our friends and ourselves with positive quotes when we are down can hurt. Active listening is one way to avoid toxic positivity

Heard Or Said Something Similar?

“Everything will be fine.”

“This too shall pass.”

“Good vibes only. Stay strong, jia you*!”

Social media rewards us for positively curated stories. This has created new challenges in how we manage the emotions of others and ourselves.

Toxic positivity: The forced blanket positive response to all difficult situations. The firm belief that keeping positive is the sole way you and others should live your life.

Though being positive is important. It is also important to let yourself experience difficult feelings. Here’s why toxic positivity is an issue and how we can be part of the solution.

Positivity Is Great.. So How Does Toxic Positivity Harm Us?

Positivity is important to keep us going in life. No doubt. ‘Focusing on what is good, will bring good’ we are taught. But like all things, e.g. Pandan Cake 🍰 , too much of something is not desirable.

Positivity becomes toxic when one rejects anything that triggers negative emotions and replaces it with positive motivational quotes or ‘vibes’. This habitual response to negativity has been found to create anxiety, depression or physical illness.

Ever tried to tell a panicking person to ‘stay calm’? I hope you didn’t!

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Wisdom from Twitter

Toxic positivity is not just an issue for your mind and body. It is an issue for others. Pushing it on others also makes you seem tone death.

The receiver of your ‘positive vibes’ comments may even start to feel bad about feeling bad. The last thing they need.

When we deny unpleasant emotions, we tend to make them bigger. Avoiding all negativity also reinforces the idea that we need not pay attention to it. This leaves it unprocessed in our psyche.

We slowly forget that emotions are not inherently good or bad but rather a guide in how we should make sense of things.

Signs of Toxic Positivity

These are some common experiences of toxic positivity to help recognise them in yourself and others.

  • Trying to ‘snap back to reality’ by saying (e.g., “it could be worse”) instead of validating their/ your emotional experience
  • Telling someone off for expressing frustration or anything non-positive
  • Hiding your true feelings and wanting it to be ‘over asap’
  • Attempting to “just get on with it” by dismissing strong emotions
  • Feeling guilty/ angry for feeling down.
  • Responding to people’s experiences with “feel good” quotes or statements about positivity

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An apt meme. Refuting reality 101.

Detoxing The Toxic Within Us

“To stay with a broken heart, with a rumbling stomach, with the feeling of hopelessness and wanting to get revenge — that is the path of true awakening.” Pema Chodron

It is easy to accept the pleasant people and situations of life. However, being able to accept the difficult people and situations is the path of spiritual growth. We find a place for deep healing and peace within ourselves.

Here’s what we can do for ourselves.

  1. Give yourself permission to feel negative and positive emotions.
  2. Journal about the emotion or sit with the emotion (if you can!).
  3. Slowly uncover the cause and see what can you do to support yourself better in the future.
  4. Talk to friends about it unreservedly.
  5. Take a walk in nature to breathe in the fresh air

Detoxing the Toxic Towards Others

Being a lover of excel tables, this is a cheat sheet to help improve the ways we talk to others having a bad time. Being an “ex-serial toxic positivity promoter”, this table saved me dozens of time!

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A table to fight Toxic Positivity


No one can be a bursting ray of sunshine every day and every hour. Accepting that it is only human will help you acknowledge the setbacks faced by yourself and others. Paying attention and processing negativity will help you better understand yourself and those around you.

*A popular Singapore term for encouraging others in difficulty

Wise Steps:

  • Memorise the chart of toxic positivity and avoid the traps you might fall into
  • Do not be afraid to acknowledge the negative emotions within you!

Help us spread more goodness to the world