The Ultimate Guide to Traveling Abroad With Your Entire Company

We took our entire staff (and families) to Costa Rica for a month. Here’s why we did it.

This past summer, we decided to take our entire company, including their spouses and kids, for a month of work and play in Costa Rica. It turned out to be one of the the best decisions we’ve made. I’m grinning ear to ear writing this and recollecting our time together.

We have staff in 5 different cities, so we were dreaming about how we might be able to get everyone together for an extended time of working, dreaming and creating. Then we had this crazy idea… and the Costa Rica trip was born.

So why did we do it? Initially, because we wanted to get out of the box, and have an adventure. Life is too short not to take advantage of great experiences. Here at Webconnex, we work really hard, but we also value family and play. We also believe that travel brings people together and expands your horizons. Experiencing new cultures and meeting new people is just good for the soul. So, if there’s an opportunity for adventure, we’re in (it’s another advantage of not being slaves to investors). If we think a crazy idea is possible, and feel like it will be good for our company, we have the freedom to do it.

It truly seemed crazy at first. Traveling to a foreign country for a month with our entire team and their families. There were so many questions; How would we handle logistics? Where could we all stay? Would everyone want to go? How would be able to actually work remotely? What about infrastructure? How would we handle customer support?

We spent a lot of time researching and dreaming, and we’re more than happy to share our experiences. One important note. (note: When planning, it’s important to shift your mindset from your current job position. I think it’s important to view yourself as a host. Your job is to make things smooth, and comfortable.)

Choosing The Destination

Choosing where to go can take some work (OK, in full disclosure, I’m a surfer and so is my co-founder Eric, and our CTO Nanno… so, a destination where we could work and surf would be ideal). I’d been to Costa Rica years ago on a surf trip and really enjoyed the country, the people and the culture. There are so many amazing places to go! Here are some of the things we considered before we selected our location. Here are the things I recommend you consider:

• Safety. I know this is obvious, but some people have traveled more than others, and it’s really important that everyone feels safe. Remember you may have folks with small kids going too. Every foreign country is different and they do have different risks than we do here at home, so it’s important to make sure your teams reads up on the local culture and make themselves aware of the local common sense safety protocols.
• Travel time & difficultly (remember you may have staff with kids): While a trip to Thailand would be epic, it’s also probably not realistic. We had about 10 small children on the last trip, so we needed to make sure the travel times and layovers weren’t unbearable. However, we also went away for an entire month, so it’s OK to put up with a bit of travel time. The travel itself is never awesome, but the sweetness of a month away makes one travel day seem short.
• Time zone — A big part of our business is supporting our customers. We take our customer support really seriously, so we think it’s important to be within two time zones of our local time.
• Infrastructure for business — Being connected to internet was most important. Since we run a software company, we needed to be able be online and have stable connection for code changes, email support, live chat and also VOIP for telephone support. Reliable internet was a top priority (we even asked our local rep there to run some internet speed checks before deciding on location). We also did research into the local wireless options. A lot of us added the local Costa Rican phone chips to our Mobile phones. You’ll want to check with your local carriers to see if you can add a local chip to your phone. Make sure whatever phone solutions you’re using here can be updated to reach you there. We use Ringcentral, so we were able to use their VIOP option.
• Accommodations — Finding a place to stay probably took the most work. We went for a month, so we needed to find something that could accommodate everyone, keep everyone together, but also provide enough privacy. We settled on a great condo complex in Tamarindo. All of the condos have at least 2 bedrooms, a kitchen and washer & dryer. The complex had a nice common pool, and it was right across the street from the beach. It worked great for us, because it was small enough that everyone was able to see each other at the pool, but large enough that people could have privacy when they wanted it.
• Access to restaurants, grocery stores & activities — It’s important to remember that a big part of your job though this is making people comfortable. We took 30+ people, so there are a lot of different needs. It’s important to find a location with a lot of options. Everyone has different interest, different budgets, and different tastes. We wanted a place with a lot of food and activity options within walking distance. There was a convenience store across the street and a major grocery store a short drive away. There was truly something for everyone.

Other things to consider:

Set expectations. It’s important to let everyone know what’s expected of them before heading out. Will you be working full time, business as usual, or a lighter schedule? We had some major software deadlines, so our development folks worked really hard. However, support is a bit lighter for us in July, so the support staff had more flexibility to work lighter hours (this year with all of our customer growth, support will be pretty busy). What is expected for meals? Will the company pick-up the tab when everyone is together? We stocked our “office” there with food for lunch and snacks while working. We also did one company dinner a week where we pickled up the tab. We also paid for several group activities (our team got to vote on what we wanted to do). What about families and spouses? What’s expected of them? It’s good to talk through everything before you get down.

Seek maximum participation. It was very important to us that we had our entire team go. While it wasn’t mandatory, it was our goal for 100% participation. We paid 100% of the expenses (flights, transportation, lodging) for every staff member and their families (even kids). Obviously, it’s not realistic that every spouse can also leave for a month, but every spouse did come down (even if only for 10 days). Having everyone, and their families there was a total blast! It was awesome for everyone to get to know each others families. I think this was one of the trip highlights. When you get to know someone’s family, you truly get to know them.

Takeaway from our experience

Honestly, we decided to take the trip because we thought it would be a ton of fun and and amazing experience. It was! But it was so much more. It drew our team closer, unified us around common goals and created deeper bonds.

I came away with one profound understanding. We knew that we had a fantastic staff. However, after spending a month together, I knew that in addition to being a great staff, I was blessed to work with truly amazing human beings. They are people I enjoy spending time with. People who care about each other, and people who care deeply about the world around them. People I can call my friends.

It truly was a once in a lifetime experience.

P.S. Last month, we let our staff know that we are heading back again for another month long trip to Costa Rica. Let the countdown begin.