La dolce vita con Canny: team retreat in Italy

· 9 min read
La dolce vita con Canny: team retreat in Italy

A few weeks ago, we came back from our team retreat in Italy. Each trip is unique, and we’re excited to share why this one stood out.

Retreats bring us new energy and ideas. We bond, brainstorm, and collaborate in person. For a remote team like Canny, these retreats offer the in-person interaction we miss. This retreat had a big goal—to launch Canny Autopilot. Here’s what went down in Perugia.


Retreats always need extensive preparation. As the team grows, we need to think through everything even more. In particular:

  • Dates: what works for everyone (or at least the largest number of people)?
  • Destination: which place doesn’t require visas (or issues visas easily)?
    • Where can most of the team easily get to?
    • We prefer places that offer interesting sightseeing/activities
  • Accommodations: are there enough beds, bathrooms, and common areas for work?
    • Ideally, we also look for accommodations with cool features like a pool, sauna, views, large kitchen, ping pong table, and more
    • Is there good wifi?
  • Food (restaurants, supermarkets, etc)
  • Work meetings: who wants to talk about what? What are some high-level decisions we should all discuss? What are we trying to accomplish this time?
  • Activities: what are we going to do for fun?

With 15 attendees, finding the perfect place is challenging. Early planning is key.

Assemble the troops

Eight retreat planners volunteered to help. We started with destination, accommodation, and food research.

Start planning asap

We sent out a survey with proposed dates almost immediately after the previous retreat. The sooner we lock them in, the faster we can start planning the rest.

Team retreat dates survey

Cross off the big things – destination & accommodations

We’ve tried different retreat formats at Canny—large cities, smaller remote towns, and something in between.

Here’s the tradeoff: in prominent cities like Tokyo, we are forced to split the group between multiple Airbnbs. It’s also harder to come together in one place and have meetings.

Canny in Tokyo

Smaller towns can offer larger accommodations (with fun perks like a pool, gym, theatre, and more) but don’t have that much around them.

Canny Cottage

Our post-retreat surveys revealed that most of the team prefers a cooler space over a larger city. This goes back to our goal—come together to collaborate and share ideas.

We took that feedback and prioritized smaller towns with fun Airbnbs. We also had to consider visa requirements and flight durations. This is when we have a spreadsheet going with viable options and columns relating to the cost of flights and accommodations.

We chose a town in Italy called Deruta. It’s in the province of Umbria, next to Perugia. Our primary reasons were:

  • Large accommodations with just enough bedrooms, bathrooms, and common areas
  • Excellent amenities like a pool, sauna, hot tub, ping pong and foosball table, gym, and even donkeys!
Canny in Italy

Collect ideas

We always set up a Canny board to crowd source ideas for the retreat.

Retreat ideas in Canny

After we have a prioritized list of ideas (based on votes, cost, proximity to our accommodations, and more), we pick the best dates for them. Typically, it’s easier to book many things on weekdays. That’s why we usually swap one or two weekdays with weekend days for work and play. This way, we avoid crowds and sometimes get a better price.

Our winning ideas this time included:

  • Truffle hunting (with a dog!) and pasta-making experience
  • Exploring Perugia (capital of Umbria)
  • Authentic Italian cooking class at our villa
Cooking class in Italy

Plan work

This retreat the biggest thing on our mind was Autopilot—our AI-powered feedback management tools that we just released. We used this time to:

  • Determine the final steps to get it ready for launch
  • Finish writing and testing code
  • Align with the rest of the team on functionality, marketing, messaging, and more 
Canny coworking in Italy

We’ve been working on Autopilot for some time. Getting everyone together in person to tackle the final roadblocks was very impactful. Communication flows faster and easier when you’re all in one room.

We also had meetings about go-to-market priorities, customer experience, and Canny’s overall direction. Everyone could voice their concerns, ask questions, and align on our future.

Make it happen

After months of waiting, we all met in Rome. Some of us explored the city for a few hours, while others drove straight to the Airbnb.

Canny in Rome

We always do a kickoff presentation to get everyone excited and set goals for the week ahead.

We made time for fun too. The Airbnb amenities were amazing—perfect for strategic chats overlooking the Italian countryside.

Canny working from Italy

During one of our days off, we went on a truffle hunting experience. A trained dog named Dado led the pack. He sniffed out the truffles, dug them up in seconds, and immediately asked for treats.

Truffle hunting in Perugia
Canny truffle hunting

After we collected enough truffles, we explored a local winery and then learned how to make pasta and cookies from scratch. All this hard work called for some rest, so we had a wine tasting along with all the food we made. It was also Ramiro’s birthday so this was an awesome way to celebrate all together 🙂

Canny in Italy

Other highlights included exploring Perugia and Assisi and cooking an Italian dinner at our villa. It’s safe to say that we all brought home some new cooking skills.

Another highlight for me was our PechaKucha night. PechaKucha is a Japanese presentation format. The presenter is only allowed 20 slides, and they have 20 seconds per slide. It’s a quick and fun way to present anything you want.

When new team members join Canny, we ask them to do a PechaKucha about their lives. Since we’re all remote, we do them virtually.

This time, we did them in person. Anyone could do one and pick any topic they liked. As a result, we learned about:

  • Bikepacking from Niall
  • Fast & Furious from Ramiro
  • Being a dad from Eric
  • Having pet pigeons from Miko

Learning about each other outside of work is always special. We find more things in common, get new ideas, and just become closer. This helps us work together better and understand each other more.

PechaKucha presentation about Fast & Furious

Canny in Italy: what we learned

As we mentioned, we send out a post-retreat survey when we come back. It helps us make the next one even better.

Here’s what we learned on this retreat.

  • Plan meetings more in advance and in more detail. Meetings can easily go off-script and overtake an entire day.
  • Try not to schedule a major public release during the retreat. This put pressure on certain team members.
  • Think about food more. Assign responsibilities in advance.
  • Ensure we’ve got sufficient Internet connection.

Overall, this was another great retreat for the books. We’re now busy with planning the 10th Canny retreat!

Canny in Italy

We hope these tips will help you plan your retreat, too. Share your retreat learnings with us too—we’d love to hear about your experience.

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

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