How to Break Through “Surface Level” Interactions to Build Deeper Connections

Is it a “man” thing? Is it a generation thing?

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

1. How deep the conversations go has a lot to do with the questions you ask

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.

2. Observe their vulnerability comfort level

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.

3. In order for them to give you a part of them, you have to give them a part of you

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 🧡

Here are some of my favourite resources to Build Deeper Connections at work and in life

Creating Powerful Connections | Sean Stephenson

Sean Stephenson shares the meaning of connection and its immense power, to even save lives. He drops nuggets of wisdom on how to connect with anyone you meet, based on what he’s observed and learned from great connectors like Richard Branson, President Clinton, and the Dalai Lama.

Empathy VS Sympathy | Brené Brown

Dr Brené Brown shares the key differences between Empathy and Sympathy, and how you can show empathy in order to ease someone’s pain and suffering. Dr Brené Brown reminds us that we can only create a genuine empathic connection if we are brave enough to really get in touch with our own fragilities.

A Powerful Display of Empathy and Holding Space | Modern Love

For the first time in decades, Lexi (Anne Hathaway) shares with a trusted co-worker that she is bipolar. See how her co-worker Sylvia (Quincy Tyler Bernstine) holds space for her in this beautiful display of empathy and love.

Own Your Voice Pod EP06: How to have Better Conversations to Build Deeper Relationships

In this episode, I’ll be sharing 5 common mistakes people make when having conversations and some suggestions on what to do instead. I literally reveal my SECRETS to human connection, learnt from 8 years of professional hosting as well as doing sales, which I know WILL transform the way you connect with your bosses, colleagues, potential employers, clients, partner, parents, the list goes on.

I’ll love to hear from you!

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!

Work with Me!

I work with individuals and organisations through speaking, coaching, and conducting workshops around the topics of Speaking, Communication, and Networking. To find out more, check out my website here:

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