Top 10 Company Retreat Ideas for Planning Your Remote Team Offsite

Written by: Nicole Smith, Founder + CEO

How do you deepen company culture and create a sense of belonging in a remote-first workplace? Many companies are wrestling with this challenge as employees no longer come into a shared office space every day. This is even more difficult when onboarding brand new team members – primarily with Slack and Zoom. One solution is hosting a company retreat! It’s an opportunity to create shared memories, build community and get everyone excited and aligned about the future.

Our company (like many) abruptly went fully remote in March 2020. Prior to that, we had a fun, highly social work environment in a beautiful heritage building in downtown Victoria, Canada. Relationships organically grew over coffee shop dates, happy hours, spin classes, and team bonding activities like lunchtime board games, 2000-piece puzzles, and Prosecco Fridays. When our office closed, we also downsized from 21 to 4 employees; the pause in global travel shut down our sales overnight. Over the last two years, as we slowly (very, very slowly) saw business recover, we leaned into building a remote team that now spans from Honolulu to Montreal.

Today we have eighteen people (eleven of whom joined in the last 10 months!). We have gotten together over virtual events, Zoom trivia and online game nights, but knew it was time to invest in a corporate retreat getaway to meet IRL. We chose the beautiful setting of Whistler, BC for a 2-½ day getaway.

When planning our offsite, I wanted our getaway to be a mix of 50% fun and 50% work-related ideas. In this post, I share all the retreat planning steps Flytographer took, from setting goals, to planning logistics, to specific programming, to team-building activities, keeping the power of designing “memorable moments” in mind.

Photo: Aly in Victoria for Flytographer. A photo of Flytographer Natalie (based in Honolulu) taking a film photo.

1. Set Offsite Goals

What are the outcomes you are seeking? Your goals are the first place to start, as they will impact everything else you plan for your company retreat. We had three:

1. Team bonding. Build trust and a sense of belonging among teams with fun shared memories. 
2. Deepen company culture and knowledge. For us this meant a refresh on our company’s 9-year history, values, our future vision and deeper insight into our individual teams, key customers and photographer community.
3. Brainstorm great ideas. We mapped out brainstorm sessions into this event so everyone had an opportunity to contribute and see themselves in our company’s future.

Photo: Emily in Whistler for Flytographer. A photo of our whole team having fun on our photoshoot together.

2. Create a Theme

Now that you have your company retreat goals, you may want to consider a motivational theme or word that you can weave throughout the programming. Our offsite theme was “Rising” because we are:

• Rising as a company after a difficult two years.
• Rising as teams that are newly formed and expanding.
• Rising as individuals through conscious leadership and adopting growth mindsets.

Photo: Emily in Whistler for Flytographer. A photo of our team capturing memories on our company photoshoot.

3. Think Through Logistics

Logistics are important to plan well in advance. In addition to the retreat location, travel, accommodation and food, it’s a great opportunity to bring in thoughtful swag as a memorable moment that can deepen team bonding. Some of our logistical considerations included:

• Inspiring Location. We wanted to be outdoors in an inspiring setting, close to nature (time of year is a factor to get good weather). Outdoor activities were a key part of our “fun retreat activities” so this was a key consideration.
• No home turf advantage. Everyone travelled there and was able to avoid the distractions of being at home. We wanted it to be in a new city that many of our team had not visited yet.
• Limit flights. Finding a place where the majority of the team was a short drive away (for considerations of cost as well as an environmental footprint). Carpooling was another great way to extend team bonding.
• Individual hotel rooms. We booked nice, affordable accommodation so everyone could have their own private room for downtime between fun activities. For many it was their first trip since the pandemic started, so we wanted to give everyone their own space and ensure they had a place to be on their own if they wanted to.
• Event space considerations. Renting spacious meeting rooms with good light that also allowed for onsite catering maximized transition time between lunches and retreat activities. Finding a meeting space with these criteria made it easier to get all the great ideas flowing faster! Ensure your retreat venue has A/V equipment so you can present slides and videos on a big screen visible to all.
• Food. As a large group, we arranged team dinners with set menus and pricing at local restaurants each night. Food preferences/allergies were collected in advance. We assigned seating each night, to ensure the entire team mixed around and had time together with different people. For our first night, we hosted cocktails and an ice-breaker exercise in an adjacent bar before moving to dinner, so everyone could get to know each other in a more casual, fun way. Breakfast was assigned a budget and each person simply expensed, so our team could start their day however worked best for them. It was great to see many organically grab breakfast in small groups! Lunches were pre-ordered and brought into the meeting rooms to make best use of all the time we had in that space.
• Memorable swag. Consider useful, eco-friendly personalized swag to surprise and delight team members and build brand affinity. We opted for branded organic cotton tote bags, cozy branded sweatshirts, and reusable stainless steel water bottles that had our retreat’s logo and individual names engraved on them. Even cooler? Our hotel had a cold water/sparkling water tap in the ice room on our floor! Our lead developer, Nik, also thoughtfully gifted everyone with a hand-carved wooden iPhone stand that he personally made! It was truly a memorable moment watching everyone’s faces light up at our first dinner when they discovered their gifts.
• Gathering feedback. Designing a quick Google survey to send within a few days post-retreat was a great way to gather feedback while the experience was still fresh in everyone’s minds.

Photo: Emily in Whistler for Flytographer. A shot of our team showing off our “Flytographer Arms.”

Photo: Aly in Victoria for Flytographer. The design on the back of our branded retreat crewnecks.

4. Design the Program

Our intent with programming was 50% work-related, 50% fun times.

Mornings were spent in a conference room learning more about the company’s past and future, our customers, photographers and teams as well as brainstorming together.

Afternoons and dinners were for fun activities that were purely social in nature. We also made sure to build in plenty of breaks for self-directed time between activities and dinner; always important for the introverts, but more so especially for everyone as many were on their first trip since the pandemic started. 

Before your start your first official session, consider setting intentions for the offsite. Include a motivational talk from the CEO, ground rules (example: phones off, be on time etc) and an overview of what they can expect over the next few days.

5. Pre-Company Retreat Team Hangouts

Before the offsite officially begins, invite each functional team (Marketing, Dev, CX etc) to meet up casually for some “pre-game warm-up” bonding before jumping in with the whole group. 

• Leadership Team Connect. Our leadership team came up a day earlier than everyone else to have dinner together and then a working brunch the next day so we could align on the goals/agenda/intentions for the week, meet IRL, and share our standout assessments (how we can work best together). We then took a break while the rest of the company arrived, checked into the hotel, and got themselves settled.
• Team Bonding. Each department lead then met up with their reports for a coffee or walk that afternoon for 2 hours to spend unstructured time together as a functional team. We did this before the first “official” offsite event (meet-and-greet cocktails and dinner), so everyone had a chance to connect with their team IRL and to ensure that no one was “coming in cold.”

6. Get to Know You (GTKY)

With so many new employees over the last few months, it was important for us to share the journey of our startup (it’s been nine years!) so they can better understand where we’ve been while we get excited about where we are going. This included a deep dive on our top customers, our community of photographers around the world, and a chance to see the “day in the life” of each team at Flytographer. We started our company retreat with GTKY content.

• GTKY Company. We showed a short, humorous video history of the company (important if you have a lot of new hires like us). You forget how much institutional knowledge and stories live in your brain! Showing the evolution of your product and brand over time is really illuminating (and perhaps cringey as you look at your OG logo!).
• GTKY Customers. This was a short video with fun facts about our top customers. We included surprise video messages from four customers who shared what they love about Flytographer. There were some tears and some laughs while reminding our team of the impact their work has in the world. Overall it was a very memorable moment for everyone.
• GTKY Photographers. Another short video with fun facts about our photographers, including a few quizzes interspersed to ensure engagement, was a great way to get to the know the faces behind our busiest and longest-term photographers.
• GTKY Teams. Each team did a 10-min presentation on “A day in the life” so we all got to see behind the scenes of Marketing/Dev/CX etc, with a fun Q&A after. Topics included our daily schedules, what teams see as their biggest challenges and opportunities in their work environment, and how other teams can help.

Tip: Weave your company values throughout your programming, wherever you can!

7. Idea Camp

Idea Camp was time put aside to connect, brainstorm and think more deeply about the company.

• Icebreaker activity. Before jumping into our big brainstorming morning at Idea Camp, we wanted to do an icebreaker activity that aligned with the theme of our company retreat. We invited everyone to share a 1-minute “Rising Story” — something (a challenging situation, event etc) that allowed them to “rise up” and see the silver lining or grow from a difficult situation. Tip: Prepare your team the day before by telling them of this activity and ask a few volunteers from your leadership team to share their story so everyone can hear examples, have time to think about what they want to share, and feel less vulnerable when it’s their turn. The team bonding that came out of this short event was really powerful as people shared sides of themselves that allowed all of us to connect more deeply as humans, not just co-workers.
• Reiterate company values, mission, vision. The leadership team took turns presenting our company’s focus and main objectives. 
• Walking brainstorm. We shared 3-5 different topics or questions and wrote them on large post-it boards that were hanging around the room. We gave silent space for people to think, write down their thoughts on smaller post-its, and then post their ideas to the question/topic board. This allowed people to be reflective and ensured everyone had quiet time to think without engaging in “groupthink.” After 30 minutes, we asked everyone to go stand in front of the question they felt most passionate about. This led to small group discussion for the next 45 mins about each of the ideas, then each group took turns sharing the best 1-3 ideas to the whole group. Note: this is only the first step in a multi-step conversation (no promises to execute ideas/timelines)!

8. Learn a New Skill: Hackathon

We took time during one lunch break to give everyone in the company an opportunity to sit with the dev team for 5-10 mins each. The dev team helped them write one line of code that was then published in our booking platform. It gave everyone a little more insight into dev work, fostered a sense of belonging, as their line of code is now in our database, and most importantly, was really fun! 

Photo: Aly in Victoria for Flytographer. The Dev Team shows the whole company how to write a line of code in our system one-on-one.

9. Make Sure to Schedule Fun

As mentioned above, we wanted 50% of our company retreat to be purely social. We scheduled this time in the afternoons between morning working sessions and team dinners. There is a lot of choice for things to do in Whistler, but here’s what we opted for, being mindful to choose activities that were accessible and comfortable for all.

• Local trivia scavenger hunt. This is free activity that was outside in the fresh air and a great way for small teams of people to get to know each other as they explored Whistler on foot. Teamwork got creative as people found unique ways to win — and we learned so many fun local facts about Whistler on top of it!
• Disc golf. A fun team building activity that is accessible to the whole team (sporty or not). Everyone received their own disc and competed in small teams on the free course available in the mountain forest.
• Team photo shoot. Of course we did! We booked a 60-minute Flytographer shoot after dinner on our second night. By then, everyone had had a couple days to loosen up, and a photo shoot was a playful way to capture fun group memories, get professional headshots of new team members and see our product in action. We also wore our new Flytographer-branded sweatshirts for a cohesive team look in the photos.
• On your own. We prepped a list of optional morning activity ideas, like a polar bear swim or hike around Green Lake, that people could do on their own or with a teammate if they chose. This offered easy ideas for people who wanted to do a little bit extra. If you are at Whistler, there really are so many other fun activities you could do, such as biking, ziplining, kayaking and wellness options (my favourite is the Scandinave Spa!).

Photo: Aly in Victoria for Flytographer. Snaps of our team having fun playing disk golf at the end of our retreat.

10. Reflection + Gratitude Closing Exercise

Research shows gratitude is helpful, powerful and rewires our brains. Giving thanks can make you happier. I personally shared my 3-minute morning gratitude practice with the team and the impact it has had on my life, both at work and personally. In this vein, we closed our corporate retreat with a reflection and gratitude exercise. The last couple of years have been wild for many of us, so doubling down on gratitude just felt right.

Gratitude Activity. Prep a Google form in advance and send a link to everyone at the start of activity. Inside the form, list the names of everyone at the offsite. Invite the entire team to spend one minute writing a line or two about each of their colleagues: What’s something you admire/appreciate or are grateful about this person?

When you come across your own name, reflect on and write what you’re personally grateful for. Answers will be anonymously collated and shared in an email to each individual privately after the retreat. This was a wonderful thing to arrive in your inbox a few days later — truly a memorable moment. It’s something people can save and refer to when they are having a rough day in the future and remember the impact they are having on their community.

P.S. If you are curious, I share my personal daily gratitude ritual on my Instagram page.

Photo: Aly in Victoria for Flytographer. A photo of Andrea reflecting & writing thoughts in a notebook.

Takeaways

Highlights:

• The road trip carpool there and back was one of the highlights — we had the best conversations with great ideas as we got to know colleagues better.
• Personalized swag was a hit and the cozy sweatshirts were great for a cohesive team photo!
• Everyone wanted more time together — this was better than the alternative, that they felt it went too long!
• So many great ideas bubble up when people feel safe to share and have more context about the company.

What I learned for next time:

• For our next company retreat, I’d work on building and maintaining excitement before, during and after the event. I think there’s a lot of opportunity to tap ideas from the entire team, get help with planning fun activities, and continue to elevate the retreat experience every year.
• I would consider doing this twice a year vs annually. The momentum and company culture was absolutely transformed. There is nothing quite like in-person team bonding!

We also would like to officially welcome our newest team members who all were able to get updated headshots during our remote company retreat photoshoot!