Hosting A Deeper-talking On-site Event with A Remote-first Team

And we all had a great time exchanging thoughts and chatting with each other :)

田少谷 Shao
8 min readJul 24, 2023
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1. Background
2. Agenda
3. Preparation and Considerations
4. Findings, Feedback and Improvements
5. Why hosting?
6. Conclusion

1. Background

We’re a remote-first startup with an office in Taipei, having around half of the teammates based in Taiwan and the rest scattered across different time zones.

This April, we organised our first and biggest team-wide on-site event in Taipei, and also joined ETH Taipei hosted by some of the teammates and many other local crypto friends.

We had already planned a fair number of activities, but I believed there could never be too many since this was a rare once-a-year opportunity for us to meet each other physically.

Thus, I came up with a three-hour event, aiming to provide an opportunity for deeper conversations and make everyone get to know each other better. (tbh, I had never considered doing this for teammates I saw daily.)

By “deeper-talking,” it’s not about this event being better than any other. It’s about recognising that people enjoy a variety of social activities, and it’s not necessary to always default to going to a restaurant and discussing daily life. We all love some novelties once in a while and make life a whole lot more interesting, don’t we?

In this article, I’ll begin by discussing the Agenda of the team event in section 2, followed by Preparation and Considerations involved in brainstorming the agenda in section 3. Later, I will share Findings, Feedback and Improvements in section 4 and then briefly mention the motivation behind organising this whole thing in section 5.

And before we get started, let’s set the mood with some quiet and delightful background music by a Taiwanese band, which can serve as the ideal choice during the activity:

2. Agenda

First session: fill out 16 Personalities Test — 20 mins

Teammates were asked to take the 16 Personalities Test and register their types on a sheet. Check out the image below to get a glimpse:

Names are removed and most results are covered by black chunks

Based on the test results, we divided everyone into four groups, although not strictly following the four categories: Sentinel, Explorer, Analyst, and Diplomat. For instance, as seen in the light grey texts, one ISFJ-A was placed into the Explorer group, while the other ISTJ-A was assigned to Diplomat-T.

Second session: group discussion — 2 hr

Next up, we dove into a two-hour group discussion where I had prepared questions that I believed to stimulate interesting discussions. Some of these questions, in hindsight, may seem a bit edgy, so I’m sharing only a fraction of the original set:

  • (Icebreaker) Cat or dog as a pet? If you have to choose only one right now
  • If Gerald Cotton, the missing CEO of a defunct Canadian exchange Quadriga, were still alive, do you think it’s worth living in secrecy in exchange for immense wealth? If yes, this means you’d willing to switch places with him; else, it’s a no. (Inspired by Trust No One: The Hunt for the Crypto King)
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  • If your loved one’s brain function was shutting down, could you accept scientists or doctors replacing the brain with the exact same data/knowledge and continue living together? (Inspired by Ship of Theseus, a thought experiment and a Japanese Manga)
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  • If your fortune telling ability revealed that your child would die young from cancer, but you’d get to enjoy a short-lived but heart-warming period before the death, would you still want to have this baby, assuming you’re not yet pregnant, so abortion won’t be involved? (Inspired by Arrival)
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  • If human civilisation were now highly advanced, but there were even more dominant existences (ET) in the universe, leaving us with two options: either staying on Earth forever without venturing anywhere (like claiming a vow of renouncing war to the universe) or flying into the universe and never returning to Earth. Which one would you choose? (Inspired by Three Body Problem)
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  • What do you believe is the meaning of life, or how do you define it?

Last session: culture sharing time! — 30 mins

This session is rather cliche compared to the previous two: talking about the pros and cons of the team’s culture. It can be compared to one’s previous work experiences.

3. Preparation and Considerations

Before we dive into the findings and feedback from the activity, I’d like to briefly mention the preparation work and considerations I took into account while planning the agenda.


  • A slide to guide the entire team through event and clearly present the questions and instructions on the screen
  • QR Codes for quick access to filling out the results of MBTIs, group discussion choices and team culture sharing
  • A comfy venue and ideally some snacks and drinks!
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Agenda Design

Please note that these considerations are specific to this particular event and may not necessarily be applicable to other scenarios.

  • Each phase was intentionally designed to involve a higher level of group participation gradually: MBTI (individual) -> group discussion -> team culture sharing (everyone)
  • By placing the MBTI session upfront, we not only had a basis for dividing people into groups but also allowed teammates to finish their pending work before the activity began, enabling them to join asynchronously
  • Positioning the group discussion before team culture sharing aimed to create a warm-up effect, encouraging open conversations and reducing social awkwardness, especially for many introverted engineers. Given that activities like culture reflection inevitably involve pointing out potential improvements in existing workflows, understanding each other’s personality types, philosophy, and values of life allows us to empathise more with others instead of being too critical or pointing fingers at each other

4. Findings, Feedback and Improvements


The main finding from dividing people into MBTI groups and then asking behavioural questions is that MBTI isn’t a strong enough indicator of our choices. The answers to all the questions turned out to be quite diverse, even among individuals with the same personality type.

While this conclusion may seem rather intuitive and obvious, I had hoped to uncover some connections between MBTIs and behavioural decisions, but unfortunately, it didn’t pan out as expected :(


Here are the comments I gathered, even if some people might find them controversial:

  1. The team event provided a refreshing and different approach, leading to intriguing conversations that don’t always happen in other settings
  2. Language proved to be a barrier for some teammates who weren’t as confident in the language the activity was conducted in
  3. It would be great to have more variety in future events, covering a wider range of teammates’ hobbies, such as outdoor activities like hiking, which is popular and easily accessible in Taiwan!
  4. Surprisingly, one of my U.S. teammates actually appreciated the inclusion of “edgy” questions, as it contrasted with the overly politically correct atmosphere in U.S. society, which sometimes hinders discussions on certain topics — a pity in some ways
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In hindsight, there are two things that I could have done better:

  • More careful planning, especially when designing the discussion questions. Even though some teammates appreciated the edgy questions, I should have sought input from people from different cultures to ensure the questions were appropriate
  • Though I did ask around to collect feedback, I should have created a feedback form, to provide a more comfortable way for shier or less straightforward individuals to share their opinions

5. Why hosting?

For those who are familiar with my technical articles from an engineer’s perspective, might wonder: “Aren’t you an engineer? Why are you hosting team events?”

On the one hand, being part of an open-minded and flexible startup, of course engineers can contribute to organising events or activities that bring teammates together for fun!

On the other hand, it all started off as something personal: I wanted to spend more time with colleagues I rarely got to see. I also found value in seeking others’ insights on the meaning of life, as I couldn’t figure it out on my own. I have always enjoyed engaging in debates with people on philosophical questions and perhaps using the answers to shape my own new philosophies of life…

For a while, I doubted whether my intentions were selfish, hosting something primarily because I personally wanted it. However, I soon let go of self-deprecation. As suggested in Humankind: A Hopeful History, we don’t always need to have perfectly moral and selfless motivations. What truly matters is that we make an effort to engage in positive actions that benefit everyone around us!

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6. Conclusion

This is a record of my journey hosting a team event aimed at fostering better understanding among everyone through a personality test, engaging discussions on philosophical and life choices, and gathering valuable feedback on the team’s culture.

Based on my teammates’ positive reactions, I’m pleased that I took the initiative to spin up this activity and I’m looking forward to hosting more in the future!

As usual, feel free to leave comments down below if you’d like to discuss anything further and hopefully, until the next one ;)

Disclaimer: I consulted with ChatGPT to help polish the article