3 Lessons for a High-Impact Off-Site

Even as asynchronous pros, we make a point of getting together once a year to connect in-person. After doubling our team size in 2025, our off-site looked a lot different this year. I was tasked with designing, planning and delivering this week and learnt a lot along the way. 

Here are my 3 lessons to deliver an impactful off-site: 

1. Balance Results with Relationships#

When imagining everyone in one room the impulse is to think of discussing roadblocks, moving projects along, and solving remote, async hurdles. My biggest lesson here is to leave room to breathe: it’s easy to overplan, and a great offsite lies in balancing the agenda between core sessions and activities. 

The magic happens in the gaps: the simple conversations, the “hallway track.”It’s vital to leave space and time for these moments. Snippets I overheard were more about building human connections, understanding how we work and also demystifying tricks of the trade we assume others know. 

Balance extends beyond the agenda into allowing team mates to take what they need. In the wise words of our COO Vanessa, “Make good choices”. Transitioning from remote to in-person can be exhausting, especially adding on travel to this. Help the team make the right choices to protect their energy levels, their ability to show up tomorrow in the best spirit, and let them know that they can communicate their needs to the event lead. No questions asked, just permission to be your authentic self. 

2. New experiences = new connections#

Beyond being together, memories are important. In a remote world you miss the birthday celebrations, trying the new restaurant down the street, or even conversation when getting coffee. 

This off-site was all about creating memories in 2 ways: activities and of course, swag. Finding activities which were relaxed, and that let the team step up or take a back seat on what they needed was really important. Building off our highlight of VR room in 2025, we prioritized visiting Basilica de la Sagrada de Familia, and unwinding with a Paella cooking class. Letting an external party take the reins and guide us through an experience helped foster camaraderie, and allowed our small team to gel further. 

My 2 personal highlights show the value in leaving room to breathe. The first night, I planned a casual, opt-in dinner. As the bar filled up, a pub quiz kicked off and who knew our crew loves a quiz, Bo knows so much about sport and Luke takes it very seriously. That unplanned shift turned a simple dinner into a highlight of the trip - the best memories often come from what you don’t script.

Another highlight came from a running list we kept throughout the year: things we wish we could do. Small ideas surfaced over 2025: sharing birthday cake, trying each other’s favorite snacks. On the final day, instead of standard hotel coffee break food, we hosted an international buffet tasting: Scottish shortbread, Philippine dried mango, sorrel from Barbados, Þristur from Iceland, and the winning stroopwafels from the Netherlands.

Both of these memories were simple, low-cost, and unexpectedly powerful. 

Of course, swag helps build identity and team belonging. High quality, useful products go a long way. Being the swag santa of the event was a role I was honoured to take on. Finding a theme which gets your team excited is crucial. Last note here is making sure everyone is included - even attendees who couldn’t attend got their swag pack to ensure they feel recognized and part of the team. 

Memories - they last a lifetime. 

3. Turn Offsite Energy Into Real Momentum#

Discovery of new projects, solutions to roadblocks, or new formed friendships. This momentum can make a huge difference to our year ahead, but it’s hard to capture. We love using Granola to capture insights from conversations, even from all the tangents and side tracked thoughts. Sharing these recordings and notes after that week helps us keep momentum, tune into our north star, and also share knowledge across the team. 

Our watercooler channel, brewtunes radio and monthly meet-ups brings our culture into our day to day lives. But off-sites cement our camaraderie, build momentum on the year ahead, and also make us unified in our understanding of what we’re doing and where we are going. 

I can’t wait for our 2027 off-site, to apply these lessons, and see how we’ve grown a year from now. 

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