4 Hidden Ways To Have Deeper Conversations

Written by Heng Xuan Teo
4 mins read
Published on Nov 18, 2022

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.

See also  Ep 14: Being Average & Not Knowing What to Do In Life (ft Tai Ling Ling)

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.

See also  Mindfulness Of Death Leads To A Fulfilling Life. Here's How.

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!

Author: Heng Xuan Teo

Data driven nerd who you may find hanging out more at libraries than at parties. Passionate about finding different ways to not fall asleep during meditation. A borderline social media luddite.

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