Distributed work is hard. Company retreats to the rescue!

Working with distributed teams is hard. A key ingredient to helping teams gel is the good old company trip. Here’s how we do it. TLDR: Meaningful work plus some fun – not the other way around.

It’s been another crazy week in San Francisco!

One dear SI tradition is to send the entire company to the US once a year. Our Berlin and San Francisco  staff get to collaborate, and we can meet customers in person and brainstorm features. Additionally it’s a great time to slot in team activities such as sailing the San Francisco Golden Gate:


While last year’s trip focused more on longer term strategy, this year was mainly tactical, and it was a huge success! It’s not exactly cheap to fly the entire team across the world, but it’s an experience I’d definitely recommend to other startups – even early stage startups.

How and what?

Monday kicked off with a Beth Steinberg workshop, giving teams a chance to pick a seasoned HR practitioner’s brain. We’ve not been able to hire dedicated product managers yet, but we have assembled a team of highly product-focused developers, so for them to soak up Beth’s learnings was a perfect way to start the week.

Our R&D department consists of 3 empowered subteams that work independently on major features. Between Tuesday and Friday each team went to visit 4 customers, presenting their current work, soliciting feedback, and discussing next steps, while also sharing the overall product roadmap. Customers were carefully selected to align with the team’s respective features. Each dev team was joined by one Customer facing person, helping the departments gel.

In parallel, I went to meet a few partners, competitors and ex colleagues to pick their brains on topics such as product growth and marketing.

Key learnings

Get everyone together in the same house – no matter what! 


We managed to secure a large AirBnB house in the Mission. It had it’s quirks and certainly looks better than it sleeps — broken airbeds, rooms without windows, no locks on bathroom doors, you name it. But having everyone in one spot was really crucial, and once we had gotten accustomed (and rented a new airbed from an outdoor supplier),  the benefits of a single house really made a difference: a huge living room and three balconies/courtyards for work, great eateries nearby, and of course Bart access.  No hotel plus rented workspace could have created the same sense of team spirit.


One customer meeting a day is sufficient

Although 4 meetings in four days doesn’t sound all that much, proper preparation and debriefing did consume a lot of effort, and in a way each debriefing turned into productive feature-discussions quickly.  Teams could be heard debating client feature suggestions  late on the balcony late at night, and I feel this level of intensity could only happen because teams were not overwhelmed by meetings but had “only” one per day.

Ensure the roadmap can be reshuffled after the trip

It’s happy coincidence that most of our current features are wrapping up in the next couple of weeks. We came back with our heads spinning, there’s just so much we need to improve on, and so many client ideas that need to be worked into the roadmap. We’re now at it, debating and prioritising suggestions, and merging them with our “old” roadmap, and while we’re not done reshuffling yet, we will have a good merge available once the current feature work is wrapping up. Next time I don’t want to rely on luck though, but proactively plan ahead.

Fun activities are important, but engaging work is crucial

We’re no strangers to fun activities: This year we went sailing, explored an Escape room, and of course had some nice dinners. Last year saw a roadtrip down to Santa Cruz plus cycling over the Golden Gate bridge, and the year before that we went hiking. But as fun as it is, nothing helps a team gel better than exciting and meaningful work. For us, that’s customer visits and roadmap discussions. No amount of sailing can beat the experience of working shoulder to shoulder with your remote peers on wowing a customer.

But, the cost?

We’ve often been asked if it’s not a bit frivolous to send all developers around the world. Shouldn’t we send just the marketers and product managers? I think not. We’ve spent roughly $40k on this trip, but the benefits outweighed everything. We reduced “man in the middle” friction by having devs talk to clients,  we ensured that our departments gel, and having a clear goal (“be ready to demo to client by date x”) helped prioritising our work. The preparation and debriefing offered deep insight to everyone involved. And our distributed team being able to gel is priceless.

Rather than sending fewer people and saving on costs we’ll probably be sending more people. We have already encouraged SF staff to come to Berlin for 3-4 weeks once a year, we’ll probably increase this to twice a year. And we’ll be encouraging developers to make the trip in the opposite direction as well – it worked exceedingly well in summer in a pilot visit, and more trips are to come.

I see this as an investment, not as a cost.

Fun fact

This is the second time already that our Berlin based staff decided to grab the opportunity by its neck and extend the company trip by a weeklong private road trip.

It’s totally fine (even recommended) for the US team too to extend the trip to Berlin for a private vacation in Europe by the way. But an entire dev team living on the road together for a week and not falling apart, that’s really something to be proud of!

In summary

Although it can be stressful at time, I can only recommend the annual trip to everyone who a) has a distributed team, or b) sells to clients far away, or c) both 🙂