A guide to running offsites for remote companies
Rainforest QA is a distributed team. We have been distributed for seven years, with have Rainforesters all over the world and a truly global culture. On this seven year journey we have learned many lessons on how to run a global company with a coherent culture. According to the team our offsites are the most impactful thing we do to drive our distributed culture. With that in mind, here are some of our tips and learnings after doing ~20 offsites in 5 years.
One caveat: this post assumes that your offsite objective is to drive positive ROI and results in your business. We do offsites because they improve our business.
First though, what is an “offsite”?
At Rainforest, an offsite is where the entire company relocates to some third-party location, and works there for a week. We fly everyone there, put everyone up in a hotel, and organize a schedule. Typically we spend ⅔ of the time doing work, especially the kind of work that really benefits from being in-person, like brainstorming and planning, and ⅓ of the time doing ‘bonding’ things.
At Rainforest we do offsites three times per year, although this has varied as we have changed in size and remote-ness.
In the past, when ⅔ of the company was based in the Bay Area, these were actually “onsites”, where we brought the whole remote team to SF for a week. Functionally they were very similar to an offsite, with a few key differences which we will get to later.
Why do an offsite?
1) Minimizing remote culture drift
For remote teams, it’s really important to have opportunities to sit together, work together, and get to know each other face-to-face without the mediation of screens, cameras, and questionable internet connections. Ultimately, our productivity and effectiveness as a team have a lot to do with how well we know each other, how much we care about each other, and how much fun we have working together. The social connections your teams create at offsites make the company more likely to succeed.
This is especially true if you have a mixed model of some folks working in an office, and some being distributed. This is the model we’ve run for 7 years, and we find that distinct cultures evolved in our SF office and the rest of the world. Bringing these cultures together has been critical to avoiding too much cultural drift and keeping the team cohesive. Clearly the design of the offsite, the agenda and purpose are also critical, and we will explore those in more detail below.
2) Some types of work are vastly more productive when in the same room
There’s a reason why remote work has become so popular amongst software companies: writing code requires long periods of uninterrupted focus; and the cadence and workflow of high-quality software teams is really compatible with being distributed. To any developer this is likely intuitive.
It’s also intuitive that there are other types of work that benefit from being in-person:
- Brainstorming. The quick-fire communication, riffing and shared whiteboard that make ideation really effective are all fairly incompatible with being remote. Yes, it’s possible to do this with tools and norms remotely, but we’ve found it more productive and efficient to do these conversations face-to-face.
- Feedback. Sensitive conversations are far more effective when body language, tone, and the myriad other ways we humans communicate are in play. We try to hold feedback sessions (on multiple levels - company, team, chapter) in-person at offsites, to maximize the quality of the feedback we’re getting on the business. In the same way that travelling to customers gets you to a different level of insight into how they use your product, and how to improve it, so does an offsite enable honest communication about the thornier topics.
- Planning. Along with the brainstorming benefits outlined above, everyone being in one place at one time makes the cross-functional meetings that are necessary to refine company- and team-level goals much more effective. Especially if your team crosses many time zones (we have colleagues from the West Coast of America all the way to Tokyo) getting everyone together for the kind of 3 hour conversations necessary for real progress is borderline impossible. Our offsites have given us an excuse to be in the same timezone, and our thrice-yearly cadence allows us to plan for and review each half-year and year segment.
3) It helps us have a global mindset
This is perhaps more nuanced, and I’m not sure that all Rainforesters would agree. From my perspective, though, the globalized mindset that we attain through travel to other cultures different from our own is critical when we work with people and companies all over the world.
While I have been privileged to grow up in a continent, with a family and access to money that has enabled near annual travel since I was a child, many of our teammates haven’t. I’ve lost count of the number of times that one of our offsite trips has been a Rainforester’s first long-haul travel. There’s something really special that happens when a Ukrainian, a Philadelphian, a Tokyoite and a Londoner are all together in some far-flung part of the world, experiencing a new culture for the first time. I’m not sure that the economic impact of this can be quantified, but it has made our company a more global and empathetic place.
The economics of an offsite
So you’re probably wondering how expensive this is. The number one reaction I get from friends when I pitch the idea of the international offsite is that it must cost a lot of money. As with all things, it’s relative. The cost depends a lot on where your company is based. If, like us, your notional headquarters are in San Francisco, it’s actually cheaper to bring everyone to a new location than to bring some of the company to SF. This is true today, and was also true when we had ⅔ of our team in SF.
The other key aspect is frugality. We tend to optimize for low cost. This means our incredible Vital Squad (the back-office team) putting a lot of energy into sniffing out cheaper locations, both in terms of flights and in terms of accomodation and food. Okinawa and Budapest are the two most recent locations - in both cases relatively affordable to get to from most parts of the world, with cheap hotels (<$100 per night) and inexpensive food.
How to run an effective offsite
These are, in order of importance, the key things we’ve learned as we’ve tweaked and iterated on the offsite concept over the past 7 years.
By far the most important choice to make: what is the purpose of your offsite? The stakes are high. Think of it like a meeting that involves everyone in the company, for a week. If you’re like most modern companies you put an extreme premium on meeting time - bring this mindset to planning your offsite. At Rainforest, we use the offsite for two key things: improving the bonds across our team, and planning and reviewing progress.
Note, for founders: you will need to wave your ‘founder stick’ a little bit to force integration if this is your aim. Humans are naturally cliquey, and it’s super exciting for everyone to catch up with long-term colleagues that have morphed into close friends. It’s critical, though, that new teammates are welcomed and that the team comes to them. Nothing is more intimidating than a large and boisterous group of people that have a lot of in jokes and are all merrily chatting away.
If there’s one piece of advice I have, it’s to find yourself the most capable administrator in your company and put that person in charge of the offsite.
Organizing one of these events is intense. Even just the individual travel to the location quickly becomes a mind-boggling matrix of flights, connections and timezones. Your organizing team needs to be seriously aligned with and excited about the purpose and meaning of the offsite to the company, and should be showered with praise as often as possible (we love you Vital Squad!!!).
Most importantly, you need conference rooms on site wherever the team is staying. We prefer a single large space that can fit the whole company, with secondary break-out spaces for individual teams. In the past we’ve tried hotel rooms, we’ve tried offsite conference facilities, and just using shared spaces in hotels. None of them are worth the cost savings. Hotel facilities are expensive for a reason - they are massively more efficient.
We’ve learned that we like to reserve the conference room for the entire stay, 24h per day, because people like to work and socialize at weird times, and there’s a lot of upside to having a default congregation space. Without a single space that is dedicated to hanging out after work, it can be easy for socializing to get siloed.
Second, you need meals on site. For the reasons outlined above, there’s a ton of upside to minimizing friction in the day-to-day experience of your team. We’ve tried almost every variation of this imaginable, and none of them are as good as breakfast and lunch where you’re staying. Dinners out are good ways to end the days off, and keep everyone focused through the afternoon lull.
It should go without saying, but good internet with WiFi capable of handling your entire team (x2 devices per person) that won’t go down, and won’t have shenanigans, is a must. Most hotels with conference facilities have already stress tested their WiFi, and good signs include the hotel having an IT technician on hand, and online reviews about fast internet.
Finally, plentiful break-out spaces are important. If you’re doing the offsite right, there will be a lot of spontaneous one-on-one and small-group conversations throughout the week. You want these to be quick and easy to convene, with minimal planning friction.
Perhaps counter-intuitively, we’ve found that you don’t want the location itself to be too exciting. You want your team to be focused on work. And there will be locations that are simply too distracting to focus for five whole days. We’ve found that ‘second-tier’ cities (no offense implied) to be ideal. For example, you probably don’t want to choose New York or Tokyo as offsite locations. In theory, everyone can take a week after the offsite for vacation and exploration, but we have a lot of parents who have to get back to look after their children. Probably the best location, in terms of achieving our offsite goals of focused work and team bonding, was a small AirBnB castle near Montpellier in rural France. Zero distractions!
That said, you want the location to be easy to get to from anywhere in the world. Ideal is close to a major international airport, with plentiful options for connections. Our goal with choosing a location is to minimize time, energy and stress spent on getting from home to the hotel, and it’s often a hard balance. For example, the castle in France was an hour’s drive from the nearest regional airport, and it added at least half a day to most of the team’s travel. Not good.
This is last not because it’s unimportant, but because the agenda is so specific to your company and what you’re trying to achieve with your offsite that it’s hard to be prescriptive. However here are some basic rules we’ve discovered over doing these many times.
First, creating plentiful opportunities for serendipity is key. The offsite is an amazing opportunity for new and valuable connections to be made across your team. From something as simple as a board-games night, to creating more structured programs to pair up people that don’t know each other to go for coffee or sit together at meals, it’s worth putting some energy into thinking about this.
Related, be careful not to pack the agenda too densely, because everyone will be too tired at the end of the day to socialize and spend time together. You want to create a good balance of structured and unstructured time - we’ve settled on roughly ⅔ structured, ⅓ unstructured.
Don’t schedule too much organized “fun”. Everyone has a different idea of fun. My idea of fun, for example, tends not to be highly aligned with long tours of cities full of dates and numbers. We’ve found it much more successful to allow the team to crowd-source ideas for what they are excited to do (visit a museum, go to a local brewery etc) and to have most evenings unstructured.
It’s also important to recognize that, in a software company, there will be a lot of introverts. A week of forced socializing is exhausting, even for those of us that thrive on human interaction. Be mindful of this when scheduling the week, and don’t expect to get important and thinking-heavy work done on the Friday. The team will be exhausted, and gentle wrap-ups, karaoke, fun time will be much more useful.
Finally, our team is optionally invited to show up the weekend before the offsite to do some exploring and socializing. This also doubles as a good way to fight jetlag. There are always family obligations and other reasons why this may not be practical, and that’s fine. But for those in the team that are willing and able to spend time before the offsite doing more tourist-y things, this is a nice compromise.
In closing, these are some of the important things we’ve learned over the course of running a number of offsites, through different company configurations and levels of remote-ness. Hopefully they can be useful to your team. Please let us know of any feedback via twitter or email!