i.
It sounds so straightforward now: you sit down, you have a Conversation (yes, that C-word), and you iron things out. Simple. That’s what teammates do, right? Talk it out when the going gets tough?
At least, I thought so. It was the basis of our company, Tribeless, after all: creating safe spaces for challenging, often necessary conversations.
But in the days — no, weeks — leading up to this decision, I did the opposite of what I preached: I hid. I avoided all contact with him. I was paralyzed by fear; by the thoughts that kept me awake at night. Anxiety was my constant friend. I was a horrible excuse of one.
I’m opening with this because I want you to know that this wasn’t easy for me. Far from it, actually. It was quite possibly the hardest conversation I have ever had, and I facilitate hard conversations for a living.
I’m sharing this with you now in hopes that you’ll be inspired to have one with the people who matter most. You’ll never know how it might change your life.
But first, let me tell you a story. The story of how Tribeless came to be.
ii.
Ariff and I first met in 2013 through a mutual friend. We went on a couple of adventures together, but lost contact in 2014. We remained distant until one day, I stumbled across his Snap — he was looking for rock-climbing buddies.
I’d just returned from San Francisco then, and was looking to reconnect with old friends to stave off the loneliness. I immediately hit reply.
So one fine day in December 2016, I joined Ariff and his climbing friends for a day of sore limbs and pushed limits. I was surprised by how well we got along, despite not having stayed in touch, so when Ariff asked if he could come for an innovation camp I was mentoring at in Thailand, I excitedly said yes.
It was in Thailand that Ariff, Shawn and I cemented our friendship. The day after New Year’s, we sat in a hotel room playing 36 Questions To Fall In Love — which is rather premonitive of the kind of work we would later do.
Upon our return to Malaysia, I invited Ariff and Shawn to the Tribeless Conversations I hosted every month. They loved the concept of it: bringing strangers together for authentic conversations. They started co-hosting with me — Ariff would welcome the guests and co-facilitate the conversations, while Shawn would cook (he’s an incredible chef). We had a lot of fun.
While co-hosting these Tribeless Conversations, we became enamored with the idea of creating a tool. I remember sitting around a table with the boys, dreaming aloud: “Wouldn’t it be so cool if people could use the tool to host Tribeless Dinners, wherever and whenever they want?”
We bounced a few ideas around, doodled them on paper, and got to work.
The tool — lovingly christened “The Empathy Box” — was simple: using a few simple mechanisms, it created a safe space for its players to open up and have a conversation over personal stories in an intimate and respectful way.
It was our baby, and we were its doting parents. We were over-protective, only taking it out at playtests and community events. I think, more than anything, we were scared. We daren’t open it up to the world, to failure, to rejection…
Until one fateful day in September 2017, when I was accepted into Ashoka Changemakerxchange, an impact retreat for social entrepreneurs in Asia.
It was the Box’s first interaction with the outside world. Would it survive?
Much to our surprise, it thrived.
It was the talk of the summit. EVERYONE wanted one. Some even wanted to work with us to create a custom version for their respective communities.
I came home to Malaysia brimming with excitement. We were onto something.
We grew more confident in the Box — and our abilities. When an opportunity to share our work at an empathy festival presented itself, I leapt at the chance. Two weeks later, Ariff and I were on a fully-sponsored flight to South Korea.
It was on that South Korea trip that Ariff and I truly solidified our friendship. It was always strong before, but because of our mixed dynamic as friends and coworkers, it had become relatively strained prior to this trip.
But Ariff took me by surprise. He wholly embraced his vulnerable side, laying his cards on the table — and giving me permission to do the same. We’d also made friends with a phenomenal group of women (using our Box no less!), who showed us what it meant to be strong and kind. They were the perfect role models for friendship, and I am truly grateful for the time we shared. (Thank you, World Culture Open, for the opportunity!)
It was an exciting time in our lives. From product development to personal development, everything we did was fresh, new and flush with possibility.
But like all good things, it had to eventually come to an end.
iii.
Ever since Ariff returned from South Korea, I could sense something was off.
Even as Tribeless gained traction, registering ourselves as an official entity, launching our inaugural Host Program and expanding to 20 cities across 4 continents within a month, making 1000USD in revenue our first month of operation, winning grants from Ashoka and the Robert Bosch Stiftung to create custom Boxes with (these)abilities (SG) and Sticky Rice Love (HK)…
Something felt off.
His performance was slipping. He was making mistakes; dropping balls he normally never would. He was stretching himself too thin, getting agitated over the littlest things and needing more breaks than usual.
Shawn and I ran after him trying to catch the balls before they hit the ground, but it was a Sisyphean task. We would sit him down and talk it out, but things would inevitably revert back to the way they were.
At first, we wrote it off as university stress (Ariff was completing his last year), but as weeks went by with no progress, we suspected the issue ran deeper. He just wasn’t…himself.
Morale started to run low. We weren’t making enough to cover our expenses. Shawn and I worked on Tribeless full-time, so we were running on personal savings and the generosity of our family. Even though Ariff only contributed part-time, ALL of us were starting to feel the pinch.
Days creeped by. The tension in the air grew palpable. Eventually, Shawn and I had to ask ourselves:
Was Ariff a right fit for the company?
We were growing at unprecedented rates. We weren’t the same company we were two months ago, let alone when we first started co-hosting dinners. We needed someone who was all-in, with the relevant skills and experience.
From what we could see, Ariff wasn’t that someone. But our friendship — and my inherent conflict-avoidance tendencies — stopped me from acting on it.
I allowed my heart and fear to get the better of me as a leader. I neglected my responsibility towards our stakeholders, our customers and our community.
And I paid the price. For weeks, I couldn’t eat. I couldn’t sleep. I suffered from chronic anxiety. Ultimately, I had to face the facts: I needed to fire one of my best friends. And I had one chance to get it right.
iv.
When he walked into our usual café, it felt like all the air was sucked out of the room. I watched him out of the corner of my eye as he placed his order and came over to our table.
“Hi guys,” Ariff said, with a hint of hesitation. I took us both by surprise by reaching up and giving him a hug hello. “Hey, thanks for coming today,” I smiled, and after a beat, gestured to the five cards laid out before me.
Response Cards are a core component of The Empathy Box. They model the ideal response (showing love, asking questions, and so on), while ensuring that the other party will be listened to (you can’t speak until your cards have been addressed by the speaker).
“I’m using the Response Cards, because I want to listen better to you.”
My intention was to create enough safety for him to feel comfortable with me. We hadn’t spoken in a while. I knew there was a lot of unresolved tension between us — possibly animosity and resentment. I had to clear the air.
“First of all, let me say I’m sorry. I’ve allowed my fear to get the better of me, and you’ve had to face a hostile work environment as a result. I want you to know that my emotions are a reflection of me, not you.”
His expression remained hard. Taking a deep breath, I continued.
“I also wanted to thank you. You’ve done so much. You’ve remained so strong and patient in spite of all the chaos that’s going on. I truly appreciate that.”
His expression softened a little. I went on.
“I want to be honest with you — I’ve observed that you haven’t been your best self lately, and that’s reflected in your quality of work. You’re my friend, and I’m here to support you. So if there’s anything you’d like to talk about…”
Ariff looked at me for a few moments. Then, thankfully, he started to talk.
And thank goodness he did, because otherwise we wouldn’t have known the amount of sh!t that was going on in his personal life. I felt absolutely terrible. I’ve been so caught up in my own fears that I’ve failed to be there for him as a teammate. As a friend.
I sat with my head down, turning possible responses over in my head. Shawn took my hesitation as a cry for help. “Would you like me to take over…?” And normally, I would’ve. GLADLY. But my knack for avoiding conflict got us into this mess; I had to be the one that got us out of it.
I shook my head at Shawn. I had a nagging feeling that Ariff wasn’t done; that it wasn’t the right time to say our piece. So I ventured: “Before we go on, Riff, is there anything else you’d like to talk about?”
Ariff looked at me and sighed. Later, I will remember this as the moment it all changed. The moment it shifted into a Crucial Conversation.
“I feel like I’ve lost you two as friends.”
Shawn and I sat perfectly still, stunned into silence. What more was there to say? Ariff had called out the elephant in the room.
How can we be good teammates… when we’ve stopped being friends?
“We don’t hang out anymore. I feel like I can’t even talk to you, because I know you’re busy and I don’t want to impose. Not just for work, but for everything else, too.” He shifted in his seat, clearly uncomfortable.
I reached out and patted his arm. “Thanks for telling us, Riff. I love you, and I care about you as a friend.” He gave me a faint smile. I take it as a subtle go-ahead for what I was about to say next:
“And that’s why I believe that Tribeless is not a good fit for you anymore.”
I held my breath and waited for his reaction. No thunder. No eruptions. Turns out the world doesn’t stop spinning on its axis, even when you’re almost 100% certain yours will.
Ariff’s expression morphed into one of understanding, concern, and dare I say, relief. “You know… I’ve actually been thinking the same thing. I feel like I’ve been weighing you guys down.”
I rushed to assuage him, though it was probably more for me than for him: “And it’s not your fault!”
Ariff nodded, his expression thoughtful. “But I won’t leave you guys hanging. I’ll just take a minor role.”
I gently took his hand. “I don’t think it’s right for you to have strings attached now. Go explore. Work at other companies. Gain more experience.” I smiled, and he smiled back. “The door is always open for you to return.”
We delved into what came next. Ariff didn’t really care about severances or compensation. What he really wanted was a say on the Box — “it’s our baby, the 3 of us,” he insisted. We agreed to work out something that felt right for the three of us when the time comes.
We didn’t lock anything down, but in comparison to the animosity and anxiety we felt at the start of this conversation, negotiating the nitty-gritty of legalities felt like a walk in the park.
“And now, we can be friends again!” I exclaimed excitedly, because it was true.
Before this, I couldn’t even look Ariff in the eye without feeling a twinge of irritation. Why wasn’t he pulling his weight? Acting as a founder? And so on.
Now that there aren’t any strings attached, I’m overcome with gratitude. Ariff has been nothing but helpful and committed. He just wasn’t the right fit, and that’s perfectly fine. Shawn and I were now free to move ahead.
And when the three of us do work together again, it’ll be just like old times —but with a renewed understanding of each other’s capacities and capabilities.
“It’s not you, but it’s not me, either”
When founders break up, it’s easy to fall prey to the single-villain narrative. But human relationships — especially when entangled in the complexities of friendship and business — are a lot more nuanced than that.
There’s a wise saying we love in Tribeless: “No one’s at fault, but everyone’s responsible.” Each of us had a part to play in this mess, and each of us owned the consequences of it. Even though we started out hesitant and resentful, by creating a safe space and establishing a shared purpose, we were able to lay our cards on the table (literally!) and just talk.
No arguments. No judgment. Only empathy, understanding and respect.
THAT, is how breakthroughs happen.
I couldn’t be more thankful for ours :)
If you’re going through something similar — whether it’s with a colleague, a friend, or a loved one — I hope this gives you the courage to have that crucial conversation.
And if you ever need some help with that, you know where to find us.
Gwen Yi is the founder of Tribeless, a global movement to create safe spaces for honest conversations around the world. We equip everyday folks with the tools and skills to do so via The Empathy Box, our proprietary methodology. To date, we have facilitated 900+ hours of Tribeless Conversations for people from 80+ nationalities and 5 continents. Will you join us? :)
