We just wrapped up our offsite in Osaka, the first time we’ve held a retreat in a location where nobody on the team is a local.

With our team now at ~10 people, gone are the days of just a handful of us meeting up and figuring out what to do on the fly. Ensuring a meet-up is productive, fun, and leaves everyone feeling more connected takes serious upfront planning.

During our last retreat in Singapore the team consensus was they’d like the next one to be in Japan.

For starters, finding an Airbnb for >10 people is a genuine challenge, at least in Japan. The only reason we opted a 10 day trip was due to the property already being booked either side. Of the handful of large houses, Osaka was roughly 50% cheaper for a large house compared to Kyoto.

A week after returning home I sent a feedback form to collect everyone’s perspective. Below is what I learned from those responses plus my own reflections.

What went well:

1. People naturally congregated with their functional groups (product people in one corner, growth in another), creating organic collaboration and knowledge sharing
2. Working on something meaty rather than known issues maximises time together
3. The Design → Engineering → QA feedback cycle took hours instead of days, dramatically increasing iteration speed
4. Getting everyone involved in using the product and discussing their experiences built shared understanding across teams
5. Visiting a country and culture that most of the team had not yet been to
6. Build understanding and empathy on the challenges each function has rather than being annoying when marketing asks you to do an unplanned task out of the blue
7. Outdoor activities give a change of environment for new types of interaction to emerge
8. Not forcing everyone to do everything works well. Some people love sports some people hate it. Let people opt in/ out as they please
9. Leaving time for unstructured time in common spaces
10. A fancy dinner with drinks on the last night gave everyone a chance to unwind and celebrate our time together

What we can improve:

1. Food is Japan is meat-heavy and a little hard to meet everyone’s dietary preferences
2. A bigger team makes everything more complex, more upfront preference gathering would have helped
3. When planning technical work, some more upfront scoping work to prevent any bottlenecks when working on planned projects together
4. People arriving at different times, missing days, and struggling with jet lag created discontinuity. A tighter arrival window would help
5. Running concurrent activities to give people some choice
6. A bigger office space in the house or ensuring a WeWork is within 10 minutes

For any remote startup considering their own team retreats/ meet-ups, the ROI is definitely high. I estimate we ship 4-6x faster when together (our changelog is living proof).