#18: From awkward to awesome: the offsite formula for remote teams
Making offsites worth the airfare
👋 Hey Diana here! Welcome to the #18 issue of the Operations Optimist newsletter. Each week I tackle questions about building operations functions in startups and share my lessons from working in venture capital.
Summer is here, and it got me thinking about travel. While my trips are limited this season with a three-month-old on my hands, I’ve been thinking about past company retreats.
I think the problem is that most companies treat offsites like extended work meetings, rather than what they should be: opportunities to connect.
After organizing events on both sides of the Atlantic for the past three years, I have found a simple approach to make them meaningful.
5 steps to plan a meaningful company offsite
1: Location, location, location
Just like in real estate, location is everything. If you have a team flying in, choose a destination that’s accessible with 1-2 layovers. You don’t want your team to be DOA by travel fatigue and jetlag.
At Whimsical, we alternated between US locations (LA, Miami, NY, Austin) and European cities (Barcelona, Lisbon, Riga) to keep things fair for our team, as we are split between the two continents.
Pick cities with reliable ride-sharing apps, major airports that handle delays well, and widespread credit card acceptance to make operations part of this a breeze (cash is not king when it comes to dealing with reimbursements).
2: Perfect timing
Plan around milestones (product launches, company anniversaries), it gives a good reason to celebrate and bond. The other thing to optimize for is weather. If you are flying folks in, might as well get some sunlight.
Skip peak tourist times, major holidays, and aim for shoulder seasons when the weather is great but crowds are smaller. This also saves you up to 30% on accommodations while ensuring good service quality.
3: Early planning is everything
Start booking flights and hotels 5-6 months ahead for larger groups. The rest of the agenda can be figured out later.
Depending on your team size, book nearby Airbnbs or a small hotel – being in the same place creates a summer camp vibe that's perfect for bonding. There is also a good chance of serendipitous encounters if people are casually hanging out in the lobby or the hotel rooftop.
4: Duration sweet spot
This one depends on your setup. If it’s a team event where you don’t have international travel, two or three days might be enough.
But for us, four full days is the magic number for our distributed team. We typically arrive Sunday and depart Friday. This creates enough time for meaningful connections without disrupting everyone's family lives too much.
5: Agenda – AM for work, PM for fun
Find a balance between work and non-work, optimizing for the latter.
Our formula is spending the AM times for work, brainstorms, all-hands and cross-functional meetings, and PM for less formal activities, preferably outdoors. Think outdoor activities (hiking, wandering around, boating). If you’ve flown people in, you might as well have a good time outside of the meeting room following up on what you covered in the morning.
The other thing to plan for is meals together. People (mostly) love to go out for food. It also gives something to talk about if things get completely awkward. Pre-book dinners for randomized groups, book tables a few weeks in advance, taking into account dietary preferences and budget ranges for the event. ChatGPT is great at creating these randomized groups based on where folks come from, their departments and interests.
Outside of work in the morning, optional outdoor fun at noon and pre-booked dinner, I’d say leave plenty of unstructured time for organic connections that your team can take charge of.
The money question
You're probably thinking: this sounds great, but it’s waaaay too expensive.
And it’s true, it’s not cheap.
But if your team is remote or distributed, these retreats are the cornerstone of your culture. They're not a mere cost, they're an investment in retention. Our team consistently rates them as the most impactful moments of their employee lifecycle.
The key is setting the right cadence (say, once per year), choosing well-connected cities (which often means better prices), and creating an agenda that maximizes value for team wellbeing.
That's it.
Here's what we covered today:
Location and timing are critical: optimize for accessibility and shoulder seasons
Start planning early (6 months out)
Four day duration is the sweet spot for meaningful connections if you have participants traveling internationally
Less structure = more authentic relationships
Resources I have found useful:
Buffer has useful breakdowns of how they organize the retreats: