My dad shared with me that he’s trying to find a group of “inner circle” to hang out with and be there for each other through challenges.

Yet, he’s noticed that conversations with his friends never go beyond surface level.

Here are 3 things I shared with him that could help if:

You find it hard to deepen conversation (esp moving formal / workplace ones)🥲

You find it hard to talk with your parents, superiors, different generation🥲

Many of us get stuck at small talk — “How’s CNY?” “How was your weekend?”

Questions you may ask that could lead to deeper conversation and an exchanging of stories are:

What’s the biggest lesson you’ve learnt in 2022?💭

What got you interested in xyz industry?💭

What were the challenges you faced in xyz?💭

How did (phase of life) change you as a person?💭

That’s why when I coach on the Art of Networking, we practice a lot on leading conversations from small talk to real talk.

Otherwise, you’ll meet many people that leave as “hi-bye” acquaintances.

Many people don’t enter the “real talk” deeper conversation stage, because they don’t even have deeper conversations with themselves.

Having spoken to people from different generations, I’ve realised a common thread in Asian upbringing: We are conditioned to hide or “get over our feelings” and move on.

My dad shared with me how his parents don’t show much emotion and rarely share about themselves. They’re priority is to put food on the table.

My dad choked up in a tear as he shared “I was never close to my dad…”

Understand that the people you’re trying to have a deeper connection with may have been taught that vulnerability is bad, and emotions and unproductive.

Being aware of that helps in managing the pace of deepening the conversation.

When you share your story, your struggles, and show your real emotions, give others permission to share theirs too.

If you want to connect deeply, be prepared to share deeply. And the only way to do so safely is to first connect deeply with YOURSELF.

Have uncomfortable conversations with yourself. All the emotions you’ve packed up over the years, they are waiting to be acknowledged.

Remember that we are all human beings with past wounds and have learnt our various responses to protect ourselves from others touching our wounds.

This is why we defend ourselves, argue, avoid conversations, or build a wall. We don’t wanna be hurt again.

My hope is that more of us can see that every single one of us, no matter our differences in age, race, culture, position, etc, have all experienced the same emotions of shame, guilt, disappointment, desire, joy and more.

Maybe then, we could aim to build bridges of compassion to have deeper, more loving conversations 🧡

If this post resonated with you, share this on social media and mention me, I’ll love to hear your insights. And share in the comments what your favourite resources around connection are!