Remote Work

Working Remote: How We Use Company Retreats to Stay Connected

A cartoon drawing of a man with a headset on while working remote.

While we pride ourselves in our ability to work remote, we also greatly value physical time together. Every six months, we host one-week-long team retreats where everyone gets together to brainstorm, get to know one another better, and have fun as a company. These retreats also serve as a way for us to collaborate together on big projects that might be more difficult to accomplish completely online.

Typically, we have one in Minneapolis (where a handful of our team is currently based) and one somewhere else. Recently, we had a retreat in Los Angeles. When it came to deciding where to go, we looked to where another majority of our team lives: California. Our company retreats also offer us a break from the usual work grind and a chance to bond over meals and conversation. 

Travel logistics

We typically have our team members fly to or (if they’re local) arrive at the destination by Monday afternoon, and then everyone heads back home on Friday. We block out hotel rooms for everyone traveling to stay at. The hotel is picked based on location so that when people arrive in the city, it’s easy to get to through a rideshare app or public transit ride. The hotel location is also decided based on where we will congregate as a team for the week. In past retreats, we’ve met at a rented coworking space or an Airbnb that fits our needs as a spot to work, meet, and hangout. 

Tiffany, Melisa, Corwin & Jake enjoying a rooftop view of Minneapolis

Tentative retreat schedule 

Each day of the week we try to accomplish something work-related but without forcing the normal daily work routine. For example, we kick-off the week by hosting an all-team meeting that we call our Company Overview. These are strategic meetings where we discuss where we are headed in terms of finances and major product launches.

We also make time for departmental meetings and brainstorming sessions. While we do brainstorm online together, doing so in person is irreplaceable. It’s also great to sit down as teams and experience those meetings together, physically. 

Another meeting we make sure happens are in-person one-on-ones with employees and managers. Rather than having one-on-ones in a conference room, we like to switch things up and make them more of a bonding experience by taking walks or sitting outdoors if possible. It’s important to note that these meetings occur separately throughout the week and are not jammed into one day. We like to space things out and keep our retreats open-ended and flexible. 

Rachel & Savannah taking a stroll along the Minneapolis riverwalk

Just for fun

In addition to the work-related happenings, we prioritize “watercooler” time at our retreats. Teammates are encouraged to take coffee breaks together at nearby cafes or go for walk exploring the area during what are normally work hours, so they can just talk and build on their relationships with each other.

We order lunch each day and also invite everyone to eat dinner at a local restaurant together each night. Dinner is optional as we understand being in-person for a week can be exhausting and that people need time to recharge. On the first night, we ask everyone to join us for a team dinner where we all kick off the week. We also schedule in fun team activities throughout the week like hiring a local artist to host a private craft workshop for our team. 

The entire team working on crafts during a recent artist-led workshop

Post-retreat

We’re always thinking about new ideas to keep our retreats fresh and encourage our staff to let us know feedback and how we can improve the overall experience. We do this in the form of an anonymous and optional survey that gets sent to everyone at the end of the retreat. We ask the team what worked for them and what didn’t, how the schedule felt and what could be better, and overall, if they have any additional feedback. The only way we can improve and get better as a team is through iteration!

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