May 3, 2023


Minute read

How To Deeply Listen And Connect, Even (And Especially) When You’re Anxious

In the depressive depths of my social anxiety, listening became the light that guided me to meaningful relationships. But it wasn’t like that at first. Initially, listening was my crutch in social situations

I resorted to playing the listener role, as I was too afraid to share my opinions. It was a coping mechanism — well, way better than drinking at least – which I did plenty of to numb my anxiety. 

But the more I practiced listening, the more it became a skill. Whether it was homeless people or business leaders, I sat, asked, and listened.

Today, listening is sacred work for me. 

As I write the last line, I cringe — uh, this sounds so new agey — but I’ll stand behind it. After all, I’ve had 10,000+ conversations over the last decade, listening and connecting with people across three continents. 

Credit: Ian Chew

Listening is when I’m surrendering to the flow of the conversation — when I’m here for the other person, not my ego.

This is what I call Deep Listening

Putting it simply, it’s listening without an agenda, so that you could fully immerse yourself in the conversation, and stay open to however the conversation unfolds. It’s just like how you would travel without an itinerary and map, being engrossed in the local scenery. 

Here are three steps to listen deeply and mindfully: 

1. Ask 

You don’t need “deep” or “creative” questions. You just need simple questions that open up the conversation. Why? In my experience, thought-provoking questions might seem impressive, but you can achieve the same effect with simple questions. 

What do simple questions look like? You already learned about them in English class: 5W1H. But here’s how I think about them a bit differently: 

  • Who, What, Where: These are usually helpful to flesh out the context of what they’re saying, so that you can ask relevant follow-up questions. 
  • When: This helps with context-setting, and has an additional superpower — they help you travel through time with the other person, which often reveals deep insights and stories. For example, “When was the last time you…” or “When did you first…”
  • Why, How: These are my favorites. As they are open-ended — they leave room for a variety of answers — they unlock the door to a deeper conversation. For example, “Why do you feel…” or “How did you realize that…” 

2. Hold space 

Edward Brodkin, a psychiatry professor at the University of Pennsylvania, defines holding space as “[offering] them the opportunity to be seen and heard fully.” 

Once you ask a question, give them time to express themselves. This isn’t about shutting up and waiting for your turn to speak, this is about gifting your kind, nonjudgmental attention towards the other person.  

Here are a few ways to hold space:

  • Acknowledge your thoughts and emotions. Then, bring your attention back to the person. 
  • As you wait for their response, remain present. You could breathe mindfully, or sip your water slowly
  • Lean into the silence — even if it’s awkward. Silence is how “we have room to listen” (h/t: Laura). Or, as Claude Debussy is attributed for saying: “Music is the space between the notes”
  • It can also be helpful to affirm that you’re here to listen, as not many people are used to having space for self-expression. 

3. Listen 

As you hold space, listen to them without an agenda

Wait, agenda? What does that mean?

Business meetings aside, most of us don’t enter a conversation wanting to evaluate, critique, persuade, or mediate. But we often end up doing so because of our “secret agenda” — our preferences and prejudices, which distort what we choose to listen or to ignore.

Even Daniel Kahneman, a Nobel Prize-winning researcher who has studied biases for decades, admitted in an interview:

“I certainly do not claim to be immune from [biases]. I suffer from all of them.”

Given the challenge, how can you listen more mindfully? 

Treat your mind as background noise

This is known as external mindfulness, and it’s about broadening your awareness to see your thoughts as a small part of your surroundings, rather than getting consumed in them. 

As you do that, focus on the other person. The energy behind your focus isn’t discipline — it’s curiosity. For example… 

  • Why did they say that? 
  • What are they really trying to say?
  • What do they mean by that word or phrase?

A listening experiment for you 

Now that you have an idea of what deep listening is, try it in the next conversation you have. 

You don’t have to do all three steps. I mean, I’m always skeptical of listicles that encourage the reader to apply A-Z… That’s more realistic than Elon Musk quitting Twitter (or can he even do so now? I digress)

Just ask yourself this one question before and during the conversation: 

“What’s so interesting about them/what they’re saying?”

As you lead with interest, listening and holding space will become a lot easier. Why? It’s a beautiful paradox: when you hand over the spotlight to others, your brilliance doesn’t dim — it shines even brighter than ever.  


Manning-Schaffel, V. (2021, August 3). What does it mean to hold space for someone? Shondaland. Retrieved February 13, 2023, from

Daniel Kahneman on Bias. Social Science Space. (2013, April 1). Retrieved February 13, 2023, from

Cohen, L. (2021, October 26). External Mindfulness for Social Anxiety, part 1: Introduction. National Social Anxiety Center. Retrieved February 13, 2023, from

About the Author: Ian Chew

Ian Chew is the founder of Deeper Conversations. Despite his social anxiety, he's had conversations with over 10,000 people, and he's been featured by top media outlets like CBC, Inc. Magazine, and TEDx. He's also taken multiple therapy and mindfulness courses, such as Power Of Awareness by Jack Kornfield and Tara Brach. Click here to visit his website.



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