29 Company Retreat Ideas to Help your Remote Startup Team Connect

Lauren Zyber

By on 07/12/22

29 Company Retreat Ideas to Help your Remote Startup Team Connect

One of the biggest challenges for remote teams is finding the time and space to genuinely connect.

In between all the startup hiring, there's of course many ways to host virtual team events, coffee chats, or holiday parties. But there’s really nothing like getting the gang together for some in-person bonding time. 


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Our own Purpose Jobs team recently had a team retreat in Detroit. We flew in our Colorado and Wisconsin teammates, hosted a community-wide happy hour, did some company planning, and ate a lot of food. Like seriously, so much food. 

We had a blast and cannot wait for the next one. If you’re planning a company retreat and wondering what to do and how to do it, we’ve got lots of company retreat ideas to make your next one a success. 

 

 

Company retreat ideas: getting started

1. Start planning early

Planning an event takes time. Planning a few days or even a week of events can be a big lift. Establish who is in charge of planning so they can get going on the details. If your startup team is small and you want everyone to be able to attend, make sure you start discussing potential dates early enough to give people a heads up and block off that time. 

 

2. Take ideas from the team for the company retreat

Whether you’re spending time in a local hub or going someplace new, get input from the team. Send out a survey to see what people are interested in. You never know who might have the inside scoop on fun things to do in that location.

 

3. Keep the details organized

Schedules, activities, lodging, food, COVID-19 testing, receipts … keep all these details straight with notes and documents. When it comes time to share the important info with the team, you’ll have everything organized and won’t miss anything. 

 

4. Check in with your team for limits

Not everyone is comfortable with doing the same things. Especially as the pandemic continues, check in with your team on their comfort-level for traveling and doing large in-person activities. If your team is small and everyone is doing the same thing, make sure you’re choosing restaurants that accommodate any food sensitivities or allergies. Going kayaking? Make sure everyone is okay with being in water and knows how to swim. 

 

5. Make things optional

Everyone has different comfort levels and preferences. Attending a giant mixer at the hotel lobby isn’t everyone’s jam, so let it be optional. And be sure to communicate with the team that not everything is mandatory. Of course you want everyone to have fun and find the retreat productive and enriching, but people get there in different ways. It’s good to respect that.

 

6. Send a packing list

If you’ve planned activities that require certain attire (swimming, hiking, snowboarding, etc.) make sure you let your team know what they should bring. For those with physical limitations, provide details that will help them best assess the activities and if they need to bring things like wheelchairs or other aids.

 

7. Send out any pre-work

If you’re planning on doing some high-level collaborative work together (keep reading to see more about that), make sure you give people some time to be thoughtful about it. For example, our team recently discussed and evolved our mission, vision and values documents in addition to some serious goal-setting. This required some thought in advance of what we need to work on as individuals and as a team.

 

8. Get the team excited

If you’ve chosen a big city, get the team pumped by sending information about that location. You could even send everyone a fun book on the city’s history. If you’re going global, help the team get more resources on the language and culture. Send little lessons in team emails or on Slack. Whatever you’re doing, get the team super excited for it.

 

Company retreat ideas: activities for connecting

1. Kayaking

Adventure out on the water with your teammates. Kayaking is a fun way to explore while still having conversations and enjoying the outdoors. Want to up the team bonding? Go canoeing to really stretch those teamwork skills. We absolutely loved our kayaking trip on the Detroit River!

team retreat - kayaking 3
Kayaking on our company retreat

 

2. Try the local food scene

Sharing a meal is always a great way to bring people together. If you’re exploring a new city, check out some of the cool spots in the food scene. If someone on the team is local, pick their brain for fun spots. Whether it’s a food truck, iconic diner, or a trendy fusion restaurant, you’ll have fun eating good food and catching up with the team. If you have a large group of people, try to book as much as you can in advance and be sure to know any COVID restrictions (if any) ahead of time.

 

3. Happy Hours

Work happy hours – maybe you love them, maybe you hate them. If you want to have one as a part of your company retreat, make sure it’s in line with what your team enjoys. Rooftop cocktails? Amazing. A few brews in the beer garden? Also a great idea. Whatever you decide, make sure you’re being respectful to the people who don’t drink and try to find a place with non-alcoholic options, or make this one optional.

 

4. Hiking

Taking a more outdoorsy route? Go for a hike! Even if you’re in a city or metro area, you can try to squeeze in a nice stroll along the riverwalk or hiking trails on the outskirts. Depending on the length of the hike, make sure you come prepared with snacks, drinks, picnic supplies, etc. 

 

5. Embrace the winter

Company retreats don’t have to only be a summer thing. You can plan an epic trip in the winter if you embrace winter sports and activities. Check out a ski lodge for skiing, snowboarding, or reading by the fire with a hot chocolate. If you’re not in the mountains, go cross country skiing! 

 

6. Surf & sand

Enjoy a tropical getaway in the sun. Whether you’re staying at an Airbnb on the beach or a hotel in a warm, coastal city, your team can enjoy good weather and get some vitamin D. Plan a relaxing afternoon on the beach to help the team unwind and chill out together. 

 

7. Explore city icons

If you choose to go to a big city for your company retreat, be sure to explore the city! Check out the local spots, the museums, the things that make that city so special. 

Coney_Island_Detroit

 

8. Start the day with team breakfast

Coffee shop, brunch spot or bagels in the office, take the time to kick the morning off right. Avoid talking about work at this time and just let the team connect as they get geared up for the day.

 

9. Leave time for rest

Make sure not to jam pack your entire day with activities. Getting the team together is fun and exciting but it can also be overwhelming and a lot of social interaction. Many people on your team might have families they need to be with too, so be respectful of people’s time and let them have some time for themselves.

 

10. Get moving!

Heading to Miami? Carve out some time for beach volleyball. Spending time in Detroit? Schedule a session of yoga in the park. Whether you’re doing a pickup game of basketball or exploring a city through bike rentals, get the team moving. 

 

11. Have a self-care day

Does the team need a little pampering? Take an afternoon off getting massages or going to a spa. Other ideas include guided group meditation, journaling exercises, or quiet nature walks. Company retreats are a great time to get recentered and focus on what matters. Health is a huge part of that. 

 

12. Roast some s’mores

Maybe it’s the Midwestern in me, but I never get tired of a good ole s’more roasted over a campfire. If you’ve chosen a city, try to find a rooftop bar or patio with fire pits. If you’re in a cabin in the woods, build a campfire (hey, that’s a team-building activity in itself)! If you’re doing your retreat in the fall (especially in the Midwest) you can often book a bonfire space at an apple orchard or pumpkin farm outside of a metro city — there are loads of hiking trails in the metro Detroit area!

hiking in michigan

 

13. Host an all-team dinner

This is one of our favorite things to do on a team retreat. The all-team dinner, which happens on the last night of the retreat, is a great way to connect, unwind, and reflect on the past couple of days. Our team is small and has enjoyed family-style meals that we can all share, but if you’re a large group, perhaps hosting a buffet or banquet style dinner would work better. Always check for dietary restrictions and make sure everyone can find something to eat. 

 

14. Spotlight the team

Whether it’s a toast at the final dinner, camp-style paper plate awards, or little shout outs throughout the week, spotlight your team members who are doing amazing work. It can be hard to give recognition when everyone is working virtually. A little recognition can go a long way. 

 

Company retreat ideas: ways to move the business forward

1. Carve out time for productive work

Don’t get me wrong: team bonding definitely can move the business forward. But if the entire week is jam packed with activities like kayaking and city tours, people might get behind on daily tasks, checking in with customers, or staying up to date on emails. It’s a great idea to plan ahead and block your calendar the week of the retreat, but also make sure you’ve prepared for the week in advance. 

 

2. Reserve a coworking space for the team

If your team is small enough, look into renting a coworking space for the couple days or week that your team will be in town. This way, you can all come together, work on high-level projects, get aligned on company vision and more. You can still plan activities in the day, but if you need some space to get work done, check out a coworking space.

team retreat - coworking
The Purpose Jobs team worked at Bamboo downtown Detroit during our company retreat

 

3. Re-align on mission, vision and values

This is a great time to get out of the weeds and focus on the purpose of your company. When everyone is together, it’s great to reconnect on why you’re all working on what you do. If the team is smaller and at an earlier stage of the company, this is a great time to move the mission, vision and values forward. If you’re still fleshing these out, spend time working on this as a team. 

 

4. Set goals — or roll them out

When the team is all together, this is a great opportunity to work on quarterly or annual goals. Whether it’s as a company, department, or individual team, take this in-person time to think big and build a game plan around it. But don’t forget the game plan. A vision without a plan will never be reality. If your leadership team has been working on quarterly and annual goals, the team retreat is the perfect time to share them with the company. 

 

5. Bring in a consultant

If you need a little help getting organized around goals, bringing in a fresh pair of eyes can help you breakthrough. Even more than goals, a consultant can help make space for productive conversations, identify issues with process and culture, and guide you in making a plan for improvement. At our recent retreat, our consultant led us in a “Start, Stop, Continue” activity where we discovered that the majority of our team wanted to stop having Friday huddles in the summer. Who knew? Having the space to be honest about what’s working and not was key for our team to move the business forward.

 

6. Do an all-team training

Getting trained on something in person is so much more productive than taking an online or virtual course. If you’ve been wanting to bring a DEI expert to the team to talk and train people on removing biases, now is the time to do it! Bring in those experts, host training sessions and, and create a space for meaningful conversations. It’s so much more productive and authentic in-person.

 

7. Give a “State of the Company” Address

Call it a townhall, all-hands, state of the union speech, whatever. Let your company know what’s going on. How are you performing? What is the leadership team working on? What is the people team working on? Are there any new benefits that will be rolled out soon? Does the company plan to go public anytime soon? What’s the path to profitability? Let people know what’s going on. The people will appreciate it.

We hope these company retreat ideas help you brainstorm your next get together with your remote or hybrid team. Our own team has found these events to be fun, refreshing, rewarding, and a chance to have quality time with the people we work so closely with.

team retreat - kayaking

If you use any of these ideas, let us know! We'd love to see how your team does company retreats. 

 

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