Team offsite plan tips and tools

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:

Team Offsite Planning Template 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:Screen_Shot_2018-01-25_at_7.41.00_PM.png
  • 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.


Brian, Product Marketing Manager and foodie extraordinaire, volunteered to put together a custom menu for our team dinner!
We took a look and changed cards around to make sure there was an even mix of presentations, brainstorming, and fun activities. Having everything available on the Trello board meant people could also easily chime in when they wanted to help out.

5) Make free time full of possibilities. 

I was very personally invested in this offsite because it combined two of my favorite things: my coworkers and my city, Chicago. For many, this was their first visit so they came in before  (or stayed after) the offsite to explore. Because of our shared Trello board, I was able to add a copious (read: obnoxious) amount of restaurant recommendations and suggested neighborhoods to explore in one singular place, rather than sending a bunch of emails.

5 Go-To Tools That Take Stress Off The Agenda

No toolbelt is complete without well, tools. Here are my go-to’s for offsite planning:


I love Airbnb for team bonding because for the event organizer, it’s a win-win: it’s way more economical than booking individual hotel rooms and frequently at offsites, people just want to hang out.  Especially if the goal is team bonding, physical colocation facilitates this organically.

A caveat is to make sure each team member is comfortable with this setup since AirBnBs mean sometimes a bathroom needs to be shared or it’s harder to have totally alone time. I made sure to ask anonymously (see Typeform below) to make sure an AirBnB was kosher. But if the team is on board, it’s golden for the planner.

For our offsite I picked two large Airbnbs with rooftop decks and pool tables, within walking distance of each other.  Because we saved so much money on the Airbnb, I was able to have everyone stay an extra day to have meetings and much coveted facetime. The most expensive part of an offsite is flying everyone in, so having the extra day was great to keep everyone focused and relaxed during the planned events and meetings.


For booking the actual offsite space, I used an app called Breather. It’s a fabulous tool for booking fun and functional office space in major cities. I picked a large space just five minutes driving from the Airbnbs. Breather spaces are prepared for work: wifi, whiteboards, Apple TVs, and bathrooms.

IMG_7164.jpgThere was plenty of room at the Breather for both sitting around the conference table and breaking out into brainstorming groups.

Eliminating all the unknowns (read: crappy wifi) makes offsite planning so much less stressful. The other nice thing about Breather is that they can help with catering. They directed me to a service which presented lots of different options for breakfast and lunch, so all I had to do was pick a few menus and get food delivered.


After last year’s offsite, I did a Typeform survey to see how we could improve. This came as a handy reference when planning this year’s offsite so we avoided boring sessions that can be easily done via video conference. We opted this year to focus more on interactive sessions like brainstorming. I used Typeform this time around to assess people’s interests, and I did a Typeform after the offsite to make sure we also learned from this year’s mistakes (looking at you unreliable internet).

Each member of the team led at least one session during the offsite, and two of my teammates joined forces to lead a candid discussion on communication preferences and best practices. Two weeks prior to the offsite they constructed an anonymous Typeform with questions around how the team communicates and asked everyone to identify areas where people thought we could improve. They presented these responses at the offsite, and it ended up being a fantastic and honest discussion about what we’re doing right and what we can improve upon moving forward.


During the offsite, it was important to keep communication transparent and centralized so things didn’t get lost in private text messages. We created a WhatsApp group which facilitated meeting up or sharing Lyfts to and from events. It was also great for sharing photos and just getting a sense of inclusion, rather than people randomly texting each other. While we usually use Stride to communicate as a team, having a temporary mobile messaging group kept our Stride rooms clear of offsite-related chatter.

IMG_7333.jpgA cooking class at the end of the trip capped off amazing teamwork with more foodie fun.

It’s very meta at Trello to use a Trello board to do projects, but in the case of this team offsite, using the Trello board along with a suite of digital tools that crowdsourced team input allowed me to punch much higher than my weight. As an individual, I was able to produce an event that previously would’ve taken a team of event planners to organize, thanks to the democratization of the planning process along with the transparency and easy access to information provided by collaborative tools.

Plus it was a lot of fun.

Next: The Best Advice For Remote Work Success From 10 Global Teams [Free Guide]

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