{"id":5236,"date":"2023-11-23T05:57:00","date_gmt":"2023-11-23T10:57:00","guid":{"rendered":"https:\/\/canny.io\/blog\/?p=5236"},"modified":"2024-03-18T16:59:37","modified_gmt":"2024-03-18T20:59:37","slug":"canny-cottage","status":"publish","type":"post","link":"https:\/\/canny.io\/blog\/canny-cottage\/","title":{"rendered":"Canny cottage near Toronto: post-retreat reflections"},"content":{"rendered":"\n

Is your team fully remote like ours? If not, did your team switch to being remote or hybrid during the pandemic?<\/p>\n\n\n\n

Either way, you know the struggles of keeping the culture alive when working remotely. Even the most introverted team members feel isolated. Don\u2019t get us wrong, we prefer and love remote work. However, we know it comes with its challenges.<\/p>\n\n\n\n

How do we overcome them? Team retreats.<\/p>\n\n\n\n

When your whole team travels together, very special connections form.<\/p>\n\n\n\n

Let\u2019s go behind the scenes of our latest team retreat near Toronto. We\u2019ll tell you all about the planning, execution, and lessons we learned from this experience.<\/p>\n\n\n\n

After every retreat, we send out a quick survey to see what the team enjoyed and how we can improve. We’ll share quotes from our team members throughout the article.<\/p>\n\n\n\n

Follow along!<\/p>\n\n\n

\n
\"Canny<\/figure>\n<\/div>\n\n\n\n\n

Why retreats?<\/h2>\n\n\n\n

Especially if you\u2019re a remote-first company, we highly recommend team retreats. They\u2019re a big investment (of time and money), but the benefits far outweigh the costs.<\/p>\n\n\n\n

We\u2019ve been doing team retreats since we hired our first person in 2018. From a 3-person to 16-person company, we\u2019ve always prioritized retreats (except for a break during the pandemic).<\/p>\n\n\n\n

Everyone always bonds so much during our retreats. People who typically don\u2019t work together start collaborating. Team members who might otherwise stay quiet come out of their shells. Everyone has a chance to share ideas, speak up, and get involved.<\/p>\n\n\n\n

Having fun together outside work helps to form special connections between people. Those connections then boost work relationships. We always feel extra energized and motivated after retreats.<\/p>\n\n\n\n

\n

\u201cRemote work is like a long-distance relationship. You don\u2019t see your coworkers for 4-6 months and start missing them. When you finally see each other, you have an awesome time together. That\u2019s what makes these retreats so incredible.\u201d<\/p>\nAndrew Rasmussen, co-founder of Canny<\/cite><\/blockquote>\n\n\n\n

<\/p>\n\n\n\n

This retreat near Toronto was our 8th retreat. We plan each of these retreats ourselves, with no external help. It\u2019s a lot of work, but we enjoy the process and feel very accomplished at the end.<\/p>\n\n\n\n

How we pulled it off<\/h2>\n\n\n\n

As the team grows, planning needs to become more and more detailed and strategic.<\/p>\n\n\n\n

Canny started with just two people\u2014me and Andrew. As the team grew, we planned retreats for up to five people, and it was pretty manageable. Finding affordable accommodations was much easier, and everyone could stay in the same place.<\/p>\n\n\n\n

Now that we\u2019re a team of 16, a lot more planning is involved.<\/p>\n\n\n\n

We\u2019re lucky to have a very passionate and dedicated team that helps organize. For Canny Cottage, six of us volunteered to help with retreat planning.<\/p>\n\n\n\n

Note<\/strong>: we created a Slack channel to get this going. Anyone can join, but everyone who does has to contribute. That\u2019s our only rule: no lurkers! \ud83d\ude42<\/p>\n\n\n\n

We typically start planning the next retreat as soon as the last one is over. Here\u2019s how it goes.<\/p>\n\n\n\n

Choosing dates<\/strong><\/h3>\n\n\n\n

Personal trips and other commitments often get planned 3-4 months in advance. We lock in the retreat dates early so everyone can block their calendars.<\/p>\n\n\n\n

First, we send out a survey to see which dates work for everyone. Usually, we do a spring and a fall retreat. Summer and winter tend to be busier for people, and we try to avoid intruding on anyone\u2019s personal lives. We also want to make sure most people can attend\u2014this maximizes the value we get out of the retreat.<\/p>\n\n\n\n

We always plan our retreats to include a weekend so we have full days away from work. From there, we keep things flexible.<\/p>\n\n\n\n

During our previous retreat in Japan, the weekend was rainy. Instead of trying to enjoy Japan in the rain, we shifted our schedule. We spent Friday outside and worked on Sunday.<\/p>\n\n\n\n

We used the same strategy this time. It works really well! It\u2019s also easier to book most things on weekdays.<\/p>\n\n\n\n

Tip<\/strong>: Choose dates early\u20143-4 months in advance. Ask for everyone\u2019s availability using a survey and optimize for the majority.<\/p>\n\n\n\n

Picking a location<\/strong><\/h3>\n\n\n\n

Once we find the dates that work, we start brainstorming destinations. Here\u2019s what we consider each time:<\/p>\n\n\n\n