Order Desk is a fully remote team spread across 12 countries. So for 51 weeks of the year, our work happens through Slack, Zoom calls, and the occasional voice note recorded between school runs and morning coffees. It’s a setup that works really well for us, and we love it! But for one glorious week a year, we close our laptops, get on planes, and meet in the same place to work, eat, and reconnect.
This year, we celebrated our 6th retreat on the beautiful island of Mauritius.
Six retreats in, the team has figured out a few patterns. Although the heart of the retreat hasn’t changed (get everyone in one place, give them space to actually be people), the logistics have evolved a lot as we’ve grown. With a myriad of issues like the travel routes becoming more complicated, and the visa landscape shifting more than once, we’ve learned what works for us and what doesn’t. A lot of that learning even happened mid-flight.
Now we’re excited to take what we’ve learned and share them with you!
The travel disasters
Every Order Desk retreat begins with one. Six for six. No exceptions.
This year alone, a suitcase showed up two full days after its owner did. Plus flight delays. Plus a few people are getting bumped onto standby. And then there was poor Izzy, whose suitcase actually exploded in transit, so he bought a brand new one…which then got lost on the way to his next destination. The man could not catch a break!
A couple of years back, someone got denied check-in at the airport because a transit visa rule had changed two weeks before their flight, even though we had already booked everything several months earlier. Another year, a visa got flat out denied, and the only reason that individual made it to the retreat was because Candice from People Ops personally emailed the Consular General at the embassy and basically asked very nicely if they’d be willing to take another look at the request. (They did. Bless them.)
So when we tell you that planning a retreat is mostly logistics and crisis management, what we really mean is: by the time everyone’s actually in the same building, eating the same breakfast, the planning team has already lived through about four crises you’ll never hear about. They’ve gotten weirdly good at it.
The food
We enjoy trying out the local flavors wherever we go, partaking in whatever the regional specialty is. Blue corn tacos in Mexico. Pho in Vietnam. Tea and cakes in Mauritius. Fresh orange juice in Florida (yes, Florida counts…leave us alone).
But this isn’t a Team Building Activity™. We had a conversation at one of the retreats about how breaking bread together is something almost every culture does, in different ways, with different rituals. And despite the team being spread across 12 countries, that was the part everyone agreed on. So trying out the local dish in the local place became our small way of saying “Thanks” to the place that’s hosting us.
Also, you can’t be in Hoi An and eat a Caesar salad. Well, you can, but why would you?
The schedule we don’t plan
In the early days, the agenda was packed. Our retreat days consisted of sessions, workshops, structured bonding stuff.
Somewhere around year three or four, the team started doing the opposite by intentionally leaving giant gaps in the schedule, and that’s when retreats actually got even better! People filled the gaps with stuff nobody could have planned for. Coffee on those tiny plastic chairs in Hoi An. The Disney Store mission in Florida. Karaoke on a catamaran off the coast of Mauritius, which I am still personally processing.
Turns out, if you give a bunch of adults who like each other a couple of comfy couches and no agenda, they’ll happily stay up until 2am talking.
The awards we do plan
The one thing we did keep on the agenda this year was the awards.
Our last retreat was the first time we ran peer-nominated Values Awards, where teammates put each other forward for embodying one of our core values. We weren’t sure if it would feel forced. Thankfully it didn’t, so we did it again! This year, two more teammates were recognized and nominated by the people who actually work with them every day, which is the only kind of award that means anything.
We also celebrated two five-year milestones. Five years at a small remote company is a real commitment.
A thing a teammate said that I haven’t been able to shake
After attending one of the previous retreats, someone told me the most surprising thing wasn’t the location or the activities. It was that everyone was exactly the same in person as they were on Slack. Same sense of humor. Same way of asking questions. Same way of caring.
I think about this a lot. Like, a lot a lot.
Most companies fly people somewhere to build a culture. We fly people somewhere because the culture already exists, and once a year, it’s just nice to be in the same room as the proof of it.
I don’t know if that distinction sounds small, but it doesn’t feel small to me.
The non-negotiables
Two things we won’t budge on.
One: We change the location every year. We’re never going back to the same place twice if we can help it. Curiosity is one of our values, and the simplest possible expression of that is “let’s go somewhere new.” (Technical caveat: Yes, we’ve been to Vietnam twice. But to be fair, one of those years was a split retreat, where half the team went to Florida and the other half to Vietnam. So for half the team it actually was new and that counts!)
Two: Villas, not hotels. Everyone gets their own bedroom and their own bathroom, every single retreat. When you work remotely, you’re used to a certain amount of quiet and privacy in your day, and we’re not about to take that away and call it “bonding”. This one is getting harder as we grow, and honestly, we’ll probably have to make peace with a hotel one of these years. We’re not there yet.
Swag is a deeply personal subject
My socks from this year’s retreat have been extra comfy on colder nights. Jamilah will defend the branded pen with her life. Travel mugs and sunglasses both have hardcore fans from previous years.
The funniest part is the family-and-friends economy that swag creates. Jamilah’s dog Raja called dibs on her towel before she’d even unpacked it. Yambo’s sister claimed his swag bag and his snacks. Felix’s partner already had plans for the new jacket before he’d even tried it on. And David’s kids immediately staked claim to his bookmarks.
There is no consensus on what the best Order Desk swag has ever been, nor will there ever be one. Just a lot of small negotiations happening in our households after every retreat.
The moment from this year people are still talking about
It’s a tight race. The ATV ride in Mexico ’23 had a really long reign as the all-time champion. Then the spontaneous night out in Vietnam ’24 came for the throne. But this catamaran karaoke situation in Mauritius might just be the new champ.
Something we stopped explaining
The cost, the logistics, the visa and suitcase saga, all of it.
It pays for itself in ways that don’t show up on a budget line. Work gets easier afterward. People make decisions faster because they actually know each other now. Ideas come out of dinners that would never have come out of a Zoom.
That’s it, really. We’re a remote team that genuinely likes each other, and once a year, we go somewhere and prove it.
See you in country number seven! 🌍
