How to easily plan a remote team offsite (hint: crowdsource it)

Trello’s marketing team is remotely distributed, so our annual offsite is the opportunity for everyone on the team to connect in person. Those connections and good vibes carry forward for many months to come as we strive to assume positive intent in all of our interactions.

Recently the team, who hails from all over the US and Canada, hopped on planes and came to the great city of Chicago to bond, learn, and grow. As the planner of this team offsite (and a native Chicagoan! Go Cubs!), I wanted to make sure the 3-day event accomplished our business goals while also having a healthy dose of bond-building fun.

The Realities Of Remote

When team members are not co-located, interactions happen on digital tools which can sometimes obscure the humanity behind the typed words, especially if people don’t see each other for long periods of time.

We have many ways of digitally connecting to remedy these issues, but nothing beats face to face interaction for team building. The good news is that a small amount of in-person interaction goes a long way in fostering connection. Managers of remote teams need to recognize this need and organize infrequent offsites that have a strong purpose, as well as fun.

So where did I begin? How to create the perfect offsite? Here’s what I learned along the way, which will hopefully make the lives of any other managers and offsite planners much easier.

This story begins like most others in my life, with a Trello board:

5 Tips For Planning The Perfect Team Offsite

A good offsite plan doesn’t need to place all the responsibility on the organizer. (Just let that idea settle in for a second.) However, it is your chance to set a clear direction for how your team should participate and make it a valuable time together.

1) Iron out a clear set of goals. 

Make sure everyone attending is on the same page (or board in this case) about the purpose of the offsite. Just like meetings without a stated goal, an offsite with no direction can feel like a giant waste of time. Having alignment on what needs to be done gives attendees a sense of purpose and a feeling of accomplishment when stated tasks are complete.

For this particular offsite, the goal was a balance of team bonding, learning about each other’s roles and projects, and longer term planning. This was stated clearly on the Trello board, and then put physically on an actual whiteboard in our offsite location. In fact, the very first thing we did as a team (besides an icebreaker sharing random facts about each other) was to articulate the goals and have them visible on that whiteboard throughout the duration of our time.

2) Identify and state the expectations. 

Bringing any team together means acknowledging different contexts. Part of the job of any offsite planner is to create a shared context for the event. Physically this is done by being in the same space, but philosophically people need to be aligned not only on goals but group norms: the standards of communication and collaboration that are expected from each other.

This can be anything as basic as “Be respectful” to designating a person to be the devil’s advocate during brainstorming sessions to alleviate groupthink. Right next to my team’s goals were the rules for engagement. We kicked the offsite sessions off by brainstorming them and putting them up on the room’s whiteboard where they stayed for the duration of the trip.

Having team input into the norms ensures they are relatable, relevant, and communicated in the team’s common language. For example, we are all big fans of Kim Scott, so one rule was “Use radical candor = Be honest and caring!” We also decided to add “Take a risk!” and “Be present” to the list. You could physically see people smile and open up once they realized the tone and expectations from each other.

3) Simplify the logistics. 

The hardest part of any offsite, the logistics portion, can be handled easily with clear team communication and digital tools. 

Here’s how:

• Initially, I sent out a Typeform getting everyone’s availability and picked the dates of the trip without a single email.
• Then I put instructions on the Trello board of when to fly in and out, and everyone booked their flights individually. Each person put a card in with their flight info so it was easy for everyone to see when people were traveling:
• In addition, I added cards to the boards with information like codes for getting into the Airbnb or Breather office space, so no one had to scramble and search for emails.

4) Have your team own the program. 

In my experience, for an offsite to be truly great, everyone involved should contribute to planning and programming so they have proverbial skin in the game. In our case, we had a list on the Trello board where team members were asked to add ideas for sessions they either wanted to see or run.

People could also vote up session ideas so we had a sense for demand. After sessions were ironed out, I added lists for each day and making the schedule was as easy as moving session idea cards from one list to another, adding time allotments to each one. Pretty soon, the schedule basically made itself.