Five Lessons from Engineering Serendipity in a Virtual Environment

startups, spark, how to engineer serendipity, social experiments

Over the past few months, I’ve been slowly experimenting with how I can take Hidden Questions online, while not sacrificing the intimacy of the relationships it builds as well.

Hidden Questions started as a question game I played with friends and colleagues, which eventually expanded to other strangers. The goal of which was to deepen our friendship within minutes rather than weeks, months, or even years. In sum, a game where each person has to answer the question truthfully, but is not required to reveal what the question is. The catch is that if the person decides to conceal the question, they have to take a “punishment” (i.e. crazy hot sauce, disgusting foods, durian, Beanboozled jelly beans, etc.). Before they decide to or not, other participants can ask clarifying questions, as long as it’s not “Is X the question?”, and bet additional units of “punishment” if the answeree chooses to conceal the question. Of course, if the answeree does reveal, the people who bet will take the “punishment” instead.

Some references:

What’s changed?

After over 30 sessions in the past 3 months, a few things have been hotfixed since the in-person game:

One-time perishable links – While not the be all end all, vua.sh lets us create a “secret messages” where only the people with the link can access the question – and only once. Once the link is opened once, it’s dead. So, this gives folks a peace of mind knowing that no one can go back and find out what the questions are. The people who create these questions are the last group/individuals who play.
One-slide Powerpoint presentations, reminiscent of Jeopardy, with increasing risk/depth factor of questions, scaling punishments with question difficulty/depth.
Mailing the “punishments” to the people I’m playing with, like Sean Evans and his team does for their show, Hot Ones, where they mail their 10 hot sauces to their guest before the interview. This way, I can keep people accountable to the punishments
Zoom, or an equivalent web conferencing tool – Social distancing at its best. Even better now, ’cause I get to play with people outside the Bay Area as well.

The five lessons I learned

Total conversation time virtually = 100%. Total conversation time in-person > 100%.
First answer makes a difference.
For group calls, preface with introspective intros.
The “extroverts” take over.
Take the bio break.

1. Total conversation time virtually = 100%. Total conversation time in-person > 100%.

Only one person/topic/conversation can happen at a time. Whereas previously when we played in-person, multiple conversations can happen at the same time often with the people in your closest proximity. Conversations tended to be more free-flowing. Web conferencing has limited the surface area of content shared in a given time period. Less content surface area means fewer touch points of kinetic energy. Less likely for people to find a spark with each other. When we played the game in-person, total conversation time exceeded 100%. When done remotely, it equals exactly 100%. Group calls, unfortunately, kill the side conversations. Now, only one or two people out of the entire group stand in the spot light.

That said, there isn’t any noticeable difference when only two people are playing.

Zoom (and other equivalent web conferencing tools) is fine, but I don’t love it.

Anyone who’s tried a Zoom Thanksgiving, Christmas or New Years celebration with either friends or family knows. Earlier this month, I co-hosted a little 2021 kickoff with friends on gather.town. Here’s the exact venue (password: strada) we designed in gather.town, if you’re curious. I found it to be a better option than Zoom for group calls. One of gather’s advantages was its ability to prioritize speakers by proximity. But with surround-sound headphones these days, it’d be nice to be able to focus on conversations by turning your avatar’s head in a certain direction, and dampening the volume of others in relation to the person you want to focus your attention on.

So, I’m still on the search for a better option. If you know of one, I’d love to know!

2. First answer makes a difference.

The first answer sets the stage for the rest of the game. Just like the “b” in y = mx + b, how deep and thoughtful the answer to the first question is determines how vulnerable everyone else will be for the rest of the game. And to set the stage, I usually start and answer the first question to help others benchmark the depth they could, but don’t have to go into. In another light, the first answer establishes the social contract for the next hour or two.

3. For group calls, preface with introspective intros.

Most of the participants (e.g. friends, colleagues, strangers) come in with little context as to what the activity will be, other than 3 things:

It’s an opportunity to get to know strangers better through answering questions.
Be prepared to be vulnerable. If you aren’t ready to let down your guard rails, it’s okay to decline for now.
And please prepare a punishment/we’ll be using what I mailed you for the game.

So, when the call starts, I start off by setting the stage before we begin the game, especially for group settings. For most people, fear, uncertainty, and an aversion to being vulnerable logarithmically increases as the number of people present increases. At the same time, given the constraints of this experiment, all of the times I’ve played this game never go past the the point when the vulnerability aversion curve severely flattens out. That usually means eight or less people, including myself. The optimal number of participants I found is four people.

The biggest part of the anxiety is often: “If I’m vulnerable, (a) I hope the others won’t judge me, and (b) I expect reciprocity.” That is the expectation. But for many, it’s hard to be the first who takes that leap of faith.

And subsequently, to reduce the anxiety, prefacing comes in two folds:

Introductions
The preamble
The rules

Introductions

It’s a knee jerk reaction for most people to regress to a definition of themselves consisting of their job title and company, especially with strangers. Just like in college, we compartmentalized ourselves by our major and year. In that context, when players introduce themselves, my goal is for them:

Not to compartmentalize themselves into a professional modality;
To force themselves to think more creatively about themselves;
To spice things up.

So, I have them introduce themselves with some permutation of the below questions. And because some of the below questions require a high cognitive load when asked on the spot, I share these with them 2-3 days beforehand (with a reminder the day before).

What unusual quirk or habit do you have that most people do not know about or would see you differently if they knew?
How did we meet?
- This question usually pops up sooner or later. Often more naturally when we played in-person. Now, when done virtually, it seems to have a high recurrence of popping up only when there’s an awkward silence. The reason I ask this one is to establish common ground for players to chat over. Sometimes, I supplement that with theirs and my first impression.
If your life were written into a book, what would the title of the book be? And what would you title the chapter you are on right now?
If you were writing a memoir of your life, is there any portion of your life you would omit from the final copy?
What is the question I should be asking you but have yet to ask?
If your life were a game of blackjack, where your life prior to the pandemic was the first card you were dealt, and your life after March 2020 was the second card you were dealt, what two cards were you dealt? And would you keep asking the dealer for more?

Once each individual introduces themselves with their name and answer to the above questions, I ask people to take a guess as to what that individual does for a living, where people can be as creative as they want. Why?

People are forced to use the right hemisphere of their brain, which warms their creative muscle up for the game.
It shows the other person you’re showing effort in wanting to get to know them better rather than resort to, what I call, “lazy questions”. It’s a little trick that I learned from one of my mentors who spent decades in behavioral analysis.
- Some examples of lazy questions:
  - How are you doing?
  - How’s the weather?
  - What do you do for a living?

Guesses are often accompanied by chuckles, if not outright laughter.

The preamble

This is something I picked up from my buddy who used to lead his own Burning Man camp.

“Before I share the rules of the game, I’d love for you to take a second to to notice who stands out to you. Whom you think you’ll like. Who might have caught your fancy. Who you plan to meet up or hope to meet up with after today. And who you think you’ll become fast friends with.”

About 10 seconds later, “Now, notice whom you just don’t think you’ll click well with. Whom you don’t like. Or whom, for reasons only known to you, you won’t catch up with after today.”

And 10 seconds after that, “Finally notice who, for whatever reason, you didn’t notice at all. Take a moment and pause… and ask yourself why you didn’t notice them.”

This usually gets people introspecting and contextualizing the information they heard in the introductions. A moment when they start turning their judgment from outwards to inwards.

The rules

Then I share the rules as I mentioned at the top of this post, as well as answer any questions others have. I played around with introducing the rules:

Before the introductions
Between the intros and the preamble
And after the preamble

And contrary to what I thought, there was no noticeable difference in people’s ability to be vulnerable. Then again, that could just mean I didn’t have large enough of a sample size for each test.

4. The “extroverts” take over.

The game itself is designed so that everyone gets multiple turns to speak. But when caught up in the moment, some people end up getting more airtime than others.

While there is a strong correlation between being sociable and extroversion (and being reticent and introversion), there is more nuance than first meets the eye. Admittedly, I don’t have the best nomenclature, but I’ll try not to regress to generalizations. So, for the purpose of illustrating this point, I’ll use another set of characterizations: the sociable and the taciturn.

The sociable thrive in new (and old for that matter as well) environments, often overshadowing the taciturn. The sociable will, more often than not, rise to the occasion and usually work to fill in the void and answer questions/comments first.

The taciturn, on the other hand, often wait for “their turn”, which in many cases, will not come unless the host gives them the opportunity to. It’s not necessarily about giving each person equal airtime. In such cases, I learned it’s not just calling on them to speak, but noticing signs of when they might want to speak.

The former leads to an uncomfortable situation of hot potato. And any shy introvert who has been in the K-12 system, is no stranger to the anxiety induced when teachers randomly call on students. Subsequently, setting up either conscious or subconscious guardrails, which is counterproductive to the experiment itself.

The latter puts an emphasis when people speak not through words, but via their actions. There’s a rough rule in psychology that 60% of communication comes from gestures and micro-gestures. 30% from tone, pace, and how you say something. And 10% from the actual content of what you say. To be more inclusive of the taciturn, it’s about noticing the 60%:

Raised eyebrows
Opening their mouth to speak, but end up closing their mouth.
Leaning into the screen
Most reactive inflections on their face or body

Note: The taciturn participants of this game did volunteer to do so, so if you’re trying to generalize to a wider population, your approach might need to be more nuanced.

5. Take the bio break.

If the game goes on longer than 1.5 hours or if I see a significant number of players’ attention waning, I usually ask if people want to take a bathroom break before continuing. Though it rarely does, it’s nice to have a 5-minute period of relief for people who need to:

Use the bathroom,
Refill their drink of choice,
Or just take some time to walk around after all that time sitting down.

Equally so, I make sure the game never goes over 2 hours.

I do want to be respectful of people’s times. Even if it’s on a weekend.
Cutting gripping conversations short leaves room for more. An excuse for the players to reach out to one another to continue the conversation.

In closing

The whole reason I started these social experiments – from Brunches with Strangers to Hidden Questions to hosting in-person events pre-pandemic – is that I love engineering serendipity. A retreat I hosted with five other friends in April 2019 resulted in one startup investment, one romantic relationship, a new home purchase, a scaled-up cooking competition, and many more new friendships that, over time, transcended geographies and professions. And, only the last result was what we had initially charted our course for. The rest, a product of the right people at the right time at the right place under the right circumstances. Serendipity.

In trying to engineer serendipity, I’ve brought people together in the proverbial “right time and place”. That’s the easy part. For the “people” and “circumstances”, I would be pretentious to say that I can pinpoint the exact variables for either. But I can say, it’s not complete guesswork. The next step, and will always be the next step, is how can I reduce the unnecessary friction and increase the potential for a relationship to begin? And systematically do so?

What can I systemize? What doesn’t need to be? And what, if systemized, actually detracts from the experience – from the relationship?

I’m not going to pretend I know everything. Even the discoveries I’ve made in this round of Hidden Questions are subject to change and nuance as well. Nevertheless, because the truth exists in some black box out there, it makes the journey extraordinarily thrilling.

Photo by nine koepfer on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!