How to Build Virtual Connections

Vulnerability is the Key to Trust and Connection

I am impressed by how everyone opened up with vulnerability and understanding in today’s group coaching session. We have touched upon questions like how to jumpstart their career remotely, how to better manage relationships, how to deal with harsh criticisms etc. Underneath the openness and deep conversations, I feel the key is how to build trust and connections virtually. If we take a step further, we will find that vulnerability is at the root of trust and connections.

“Embracing our vulnerabilities is risky but not nearly as dangerous as giving up on love and belonging and joy — the experiences that make us the most vulnerable. Only when we are brave enough to explore the darkness will we discover the infinite power of our light.” — Brené Brown

Vulnerability makes us human, and it’s the humanity that makes people care to listen. This is why comedians like Ali Wong take on the risks to embarrass themselves. This is also why terrible rejection stories go viral. We don’t need yet another Instagram photo. What we really need is a peek into your not-so-perfect-world, so that we can relate to you and human together.

Last summer, I was taking a six-week storytelling class at Google and the final homework is to deliver a story we haven’t told before. Most of my classmates are in their 30s to 40s. Most have been through some personal traumas in their childhood. Most of their stories are loaded with heavy baggage. On the other hand, I can’t find anything significant enough to tell from my personal journey.

By week four, I stayed after class to ask my coach for guidance. I told him the story of how I first met Chris. Unlike others, mine was light, sweet, and very me. He told me that the most powerful stories often have few layers, and he thought my story would inspire the class. He asked me to tell my story in front of the class, and I ended up receiving amazing feedback.

This lesson taught me that vulnerability doesn’t have to be heartbreak, embarrassment, or rejection. The key is to simply be yourself. The more you can be yourself, the more people will trust and like you. If you can overcome the challenge to put yourself out there, people will reward you with connection, laughter, and love.

  • Business: When I interned at Google last summer, one VP shared this advice with me. This is especially in a highly competent workforce like Google. It’s way better to ask your smart colleagues because smart people can easily detect bullshit. You don’t want to fake that you have answers. If you are comfortable, you can go above and beyond by being truly honest with your colleagues, competitors, and potential customers. Since so few people are willing to do so, you suddenly rise above the competition. This pays off huge long term. 
  • Relationships: Chris and I know that we can be vulnerable and talk about anything that crosses our minds. This has taken a few years to build, but it has been the most powerful investment.

In the past few months, the pandemic has challenged us to adopt new forms of social connections. To get through this tough time, we need to choose connection over division.

That said, there’s a certain type of people we want to connect right now. It is important to set boundaries in digital connection and being selective about who to connect with. As a result, many of us have got to build deeper relationships and critical conversations with the people we live with. However, this intention has made serendipitous conversation and weak ties even harder to build.

Before we talk about how to build virtual connections, it is important to make sure we have taken care of ourselves. Remember that self-care is the most selfless thing we can give ourselves.

Here is how I take care of myself

  1. Being fully present and focus on where I have control over.
  2. Access my inner desire and intuition through meditation
  3. Write down 10 things I’m grateful for
  4. Do morning and evening workout
  5. Create rituals to celebrate daily life (e.g., intentional cleaning)
  6. Play the piano or make art to activate other senses
  7. Do one fun activity every day (e.g., lie down on the couch)

If you are looking for more self-care ideas, check out Quarantine RX.

After we learn to take care of ourselves, we can extend this connection to family, friends, and colleagues:

Connect with new friends

  1. Go for a walk with someone on the phone
  2. Reconnect with friends you’ve fallen out of touch with
  3. Quarantine Chat pairs you with another person to talk about anything
  4. Mon Ami pairs you with senior citizens through a volunteer phone bank

Connect with colleagues

  1. Host virtual happy hours to celebrate over your social lubricant of choice
  2. Do the same activity together from afar (e.g., virtual lunch, work sessions)
  3. On Deck created a virtual retreat playbook to help build trust and connection across teams
  4. Webflow created writing prompts to help team bond over Slack asynchronously

After this pandemic, I hope that these important realizations— value in-person connections, have more compassion for ourselves and others, and develop a deeper sense of service and humanity — will change our lives for better.

How I Plan a 3hr Retreat on Zoom

Step-by-Step Playbook for Remote Retreat

Last weekend, I held a remote retreat for my 7-person team at LivingOS. While I’ve planned many offline events before, I have never planned a remote retreat before. I did a quick search on my digital brain and several trusted knowledge hubs, but I didn’t find a playbook that fits my need.

To design a retreat that works for my team, I created a Messenger Poll to let my team vote on what they want to do.

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I also biased my team towards the items I want to discuss with * 🤓

Pre-Work: What We Did Ahead of Time

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  1. Personal Value Exercises: Due to popular demand, I created a worksheet to help my teammate find their top five personal values.
  2. Organizational Value Exercise: I created a team pulse check using the question framework introduced in The Five Dysfunctions of a Team by Patrick Lencioni. This survey helped me realize that my team struggled with the avoidance of accountability. While the book has recommended a few ways to address this dysfunction, we are still iterating to figure out which remedy works best for us.
  3. Write up Your Best Creation: Each member on my team owns a separate channel, and we love to celebrate our successes as a team. This not only helps everyone feel valued but also gives us the momentum to keep moving forward.

During the Retreat…

We split the three hours into bonding, brainstorming, and strategy.

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Full Retreat Agenda


We started the retreat with the Yes And Story Exercise from Improv.

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The key is to be fast on your feet and build on what your previous teammate has said. Since you won’t have time to plan ahead, you need to pay full attention to what the previous person has said. You also have to take action — even though you don’t know what you are doing — which perfectly resembles the culture of our early startup days. After all, if you don’t fire bullets, how can you win the game?

After the ice breaker, we each used a few personal stories to introduce the personal values important to us at the moment. This gave us the context that we don’t normally talk about at work and helped us better understand each other. Due to privacy, I’m not going to share the personal values of my team.


Before we get to LivingOS Principles, I want to feature what my team has accomplished in a couple of weeks 🎉

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Claire’s Awesome Work
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Elaine’s Awesome Work
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Mona’s Awesome Work
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Juhan’s Awesome Work
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Frank’s Awesome Work
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Charlene’s Awesome Work
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Chris’s Awesome Work

After getting a sense of each person’s scope and progress, we spent some time revising the LivingOS principles I drafted earlier. We soon found out that this project scope is larger than we thought. For example, we began to wonder:

How might we work on bigger projects together?

How might we set a universal objective?

We’ve got great progress on these questions, and I hope to share our learnings with you in the coming months.


Building on the brainstorming inspirations, we brought many great ideas to the brainwriting session on Miro. We went through a few user stories, fleshed out the customer perception for LivingOS University, and identified a few big opportunities to work on.

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We didn’t get to cover everything, so we decided to finish up the next brainstorming stages asynchronously and sync up in the weekly meetings.

Overall, I have learned a lot from my team and plan to run the next iteration in the near future.

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