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Feb 20, 2019 18:12:46

Offsite No.1

by @hum | 1131 words | 🐣 | 215πŸ’Œ

Sarah Hum

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Last week was our first team offsite. We brought everyone together in Lisbon for some good old team bonding. 

As a remote team, it's so important that you get face time with everyone. Equally important is actually hanging out in person. With our 4th teammate joining, we felt that this would be a great opportunity to meet up.

If you're building a remote company, don't underestimate the benefits of meeting in person. Here are some highlights from our week together and why we're already so excited for our next one!

Pre-offsite planning

Since we were a small team, planning was fairly easy. We picked a city (Lisbon), we chose a neighborhood (Alcantara), and we set dates. There's was a coworking space nearby that would be perfect for working during the day. Everyone booked their own flights and Airbnbs and we were set.

There was no specific goal for this trip other than getting to know each other.  Something about being behind a screen hides a lot of everyone's personality. We planned to work together during the day. Outside of that, we had time and space to just hang out and explore Lisbon.


We weren't goofing off the whole time! We worked a pretty regular week. Having a space with reliable internet is crucial. We worked from Coworklisboa, one of the oldest spaces in Lisbon.

We were able to do our team syncs and other meetings together. Andre ran a great session about customer success at Canny and how we can do better.

My favorite was the PechaKucha. It's a presentation format where you show 20 images for 20 seconds each. Our theme was [Your Name] 101. It was a great way to get to know more about each other. Great for new teammates!

Some things are really nice about going into the office and seeing everyone in person. We won't have that luxury every day as a remote team but when we do, it'll be all the more special.

Food & sangria

β€œOne of the very nicest things about life is the way we must regularly stop whatever it is we are doing and devote our attention to eating.” – Luciano Pavarotti

We had lunch and dinner together every day. After hours of working, it's great to take a second to chill out. We had a lot of wine and beer this week but the drink of the week was definitely sangria. Particularly because, on Chinese New Year, we order 2L but got 4L instead. Lots of laughs and good conversation were had.

I highly recommend cooking dinner yourselves. One, it's cheaper. Two, there's nothing like enjoying a home-cooked meal together.

The highlight is definitely the Sunday pork roast. Slow roasted in the oven for 6 hours with vegetables. And of course, Andrew made some homemade sangria.

Planned activities

We played most things by ear but thew in a couple of planned activities for structure. Our activities of choice were:

  1. An escape room
  2. A cooking class

I highly recommend them both. Escape rooms are becoming a tradition at Canny. It's fun to race against the clock and stretch our brains differently. If your team is bigger, split up and do the same room to see who escapes first (or who doesn't).

Cooking classes are awesome for a local experience. We baked pastel de nata together. They were the crispiest, melt-in-your-mouth, tarts we had all trip.

Some other ideas:

  1. Scavenger hunt
  2. Potluck
  3. Boardgame night
  4. Arts and crafts
  5. Lunch-and-learns/lightning talks
  6. Cooking competition


Outside of planned activities, we left space for being spontaneous and downtime. We did a lot of hanging out and watched a bunch of Friends. One night we ended up at a bar where musicians were performing fado, a Portuguese genre of music. Definitely a highlight.

During the week, we were also working closely with a marketing candidate. Learning from our previous mistakes, we made sure to actually experience working with them.

By the end of the week, we made her an offer and welcomed Elen to the team!

We wanted to take advantage of everyone else being in the same city so Elen flew out to Lisbon on Sunday. Just in time for the pork roast and team photos. It was short but sweet.

One beauty of working at a small company is flexibility for these magical things to happen. They often turn out to be the more memorable parts of the trip.


What a shame it would be if we didn't take some time to see Portugal! On Saturday, we rented 3 scooters and rode out to Sintra.

We explored the underground caves at the Quinta da Regaleira, enjoyed the views at Castelo dos Mouros, and had great tapas in downtown Sintra. 

If the weather's nice, get outdoors! Go on a hike, see the sunset. We're indoors and on our laptops most of the time.


Photos & photoshoots

Whether you hire a photographer or do it yourself, taking photos is a must! Your whole team isn't together very often. Did you even meet up if you didn't take a selfie together?

Get in the habit of documenting your time together. It's great for the memories but also they'll come in handy down the road.

We had a lot of fun doing photoshoots. All you need is a cool location and some natural lighting. All we used was an iPhone balanced on a tripod. Here we are on our day trip to Sintra with our scooters.


It's also a great opportunity to capture images for your company about page.

How much everything cost

We had no idea what to expect going into it how much everything was going to cost. We figured four people in Lisbon for a week wouldn't break the bank. We naturally err towards saving money when possible but splurged a little here and there.

Canny covered flights to and from Lisbon, accommodations, food, transit, activities, and coworking for the week. We estimated it would cost around $1,000 per person.

After all was said and done, here's the breakdown (in USD):

  • Flights: $1,309
  • Accommodations: $905
  • Food: $997
  • Transit: $294
  • Activities: $653
  • Coworking: $182

Total: $4,340 ($1,085 per person)

Pretty much exactly our estimate! Now we have a pretty good ballpark for future offsites. We like the idea of doing one every 3/4 months. Especially while we're still a small team. Of course, the numbers would be quite different if we were in an expensive city. Lisbon seems to have a pretty average cost of living.

If I were to make one adjustment, I would spend less on food and more on activities. Saving on food is easy: cook meals at home. It's much cheaper and you get to bond as a team. I would rather spend that money on another team activity. Skydiving anyone?

Up next:

What we're thinking about for our next retreat (Hackathon, more cooking, one house, etc.)

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