Tuesday 27 September 2022

Why I took my team to Costa Rica for a month

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The day we founded Roadmunk we didn’t talk business plans or product strategy. Both me and Tomas, my co-founder, only had one topic on our minds: culture.

It was a freezing winter day in 2012, so we holed up at Tomas’ apartment, made tea, and talked about the values we wanted to bring to our company.

What kind of team did we want to build? How would our personal beliefs be reflected in our business? By the end of the conversation, we knew we wanted to create a company with culture at its core.

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When we talked about culture, we didn’t just mean pingpong and snacks. (Although those are fun to have.) We wanted a culture that went deeper than a bag of trail mix.

For us, it’s about balance: between career and fun, between hard work and freedom, between business and friendship.

It can be tough, because although our team is small, it’s split. Our operations staff works from Toronto, while our dev team works in Waterloo. I’ll often go weeks without a face-to-face with some of my employees.

The decision to ship our whole company to Costa Rica for a month came from a desire to truly live by our culture-first mandate. I admit, I wasn’t immediately on board. There was the cost, and the optics  —  to our investors, to our clients. But we didn’t want culture to be something that we said we cared about, but didn’t actually live and breathe.

I’d never been big on formal team-building  —  it implies you don’t have a team to begin with. (Plus, it’s corny.) We were also very aware that so much intense time with coworkers would come with its share of challenges. But that actually reinforced why we were going.

This was about getting to a deeper level  —  even if that meant uncovering some muck along the way. It was about finding an even more intuitive cadence within a team that was already in sync.

The logistics

Step one: Find a house with a strong internet connection.Step two: GO FOR IT.

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Okay, it wasn’t that simple. First, this didn’t happen overnight. Although we’re still a young startup, it took three years to get our company to a place where an extended remote work excursion was feasible. After browsing Nomad List and considering several countries in Central America, we settled on Costa Rica. The beach was too hot and distracting, so we found an amazing Airbnb in Monteverde, a town located inland, where the weather is more temperate.

Technical considerations included security, privacy and (most importantly) internet. We made each potential host send us a screenshot of an internet speed test. Maybe they thought we were neurotic. (Maybe we are neurotic?) But it was better than having to turn around and come home because we couldn’t do any work.

Why a full month? It’s long enough to adopt a fresh mindset, take fun side trips, and enjoy a solid chunk of winter away from home. (Side note: it wasn’t a rule. Several employees came for two weeks rather than a month  —  their choice.)

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Roadmunk covered room and board, plus the cost of transportation to and from Monteverde. Employees just had to cover their flight and any after-hours activities. Some non-work highlights included a crazy, mile-and-a-half-long zipline over the canopy, trips to the coast for the weekend, and a gorgeous hike through Monteverde.


The house itself was big enough to comfortably sleep our team of more than 10 full-timers. It had several guest cabins, so people could have their own space to sleep. And there was an enormous amphitheatre on the property, where we did yoga every day. All in all, an awesome spot to find balance between working hard and relaxing hard.

What happened

There were, obviously, some questions going into the trip. Would we actually be productive? Would we drive each other nuts? What if we all got sunburns?! In the end, the advantages definitely outweighed the anxieties.

We learned each other’s rhythms

There’s a lot you can understand from cooking with another person. During the trip, two people were assigned to cook each meal. Which meant that employees who rarely overlap had the chance to collaborate on a fun project: making food!

When it was my turn to cook with Sameena, our head of product, something very cool happened. We chatted for about two minutes at the beginning of the process, then completely immersed ourselves in chopping and prepping. I don’t think we said another word until the meal was complete. We were completely in tune.

At the office, things are hectic. But by cooking together and living together, we got on the same wavelength. Employees who don’t regularly work together were able to reach a level of trust and understanding they never would have otherwise, while employees from the same teams were able to strengthen their bond.

New space, new perspective

We broke through a few stubborn business roadblocks during our time in Costa Rica. Getting out of our office  —  and far away from our usual frustrations  —  gave us some serious clarity. We nailed down our mission statement. We cracked a design conundrum on an upcoming feature that had been nagging us for months. We had a lot of high-level conversations about where the company will be going in the next 2, 3, 5, 10 years. And we proved that remote work can be just as effective as staying put in your hometown office.

Which isn’t to say it was all clear skies. One UX dilemma, in particular, caused a lot of friction: there were definitely some tense back-and-forths as we worked towards a solution. That’s where walks came in useful. (I’ve always loved the idea of 1-on-1 walking meetings.) By making space for daily walk-and-talks, we were able to face stubborn problems from a more relaxed perspective. And yeah, the scenery didn’t hurt.

Empathy, empathy, empathy

This was my first time in Costa Rica, and I was completely taken with the warmth of the community where we stayed. My impression of the Costa Rican culture is that it is based heavily around relationship-building. Canadians may be known for being polite, but we also keep our distance. By immersing myself in a very different milieu, I gained a new perspective on my relationships  —  both with my team and Roadmunk users.

Key word here: empathy. Spending a month in a house with your coworkers, you inevitably get closer. Guards come down, stories get told, you learn what makes them tick and what irritates them. And that rubs off on our users.

At the end of the day, building a world-class product is about understanding your customers’ motivations and needs, then putting yourself in their shoes and delivering a tool they will love using. Taking a month to focus deeply on the human side of our business offered a profound sense of empathy  —  which inevitably boosts the bottom line

The takeaway

Culture isn’t a gimmick or a “nice to have.” On a business level, our trip was entirely justified: during our month away, we surpassed several sales milestones. It was the strongest month we’d had up to that point.

This is why putting culture first doesn’t mean putting business second. I strongly believe that everything flows from culture. As Roadmunk gets bigger, it won’t always be possible to take our whole team to another country for a period of remote work. But the fact that our core team shared this experience will positively impact the company for years to come.

Only good things can result from a team that knows each other and grows together. That’s why I took my team to Costa Rica for a month. Not just to build an exceptional culture. But to build an exceptional culture that would translate into an exceptional business.

This post was originally published on the Roadmunk blog. Read the original article here.

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Q24N is an aggregator of news for Latin America. Reports from Mexico to the tip of Chile and Caribbean are sourced for our readers to find all their Latin America news in one place.

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