Plus IRL: How to plan your first remote team offsite

What we learned from our first in-person offsite as a remote company.

Last week was Plus's first ever offsite. We rented out a condo building in Chicago for a week, and our twelve person team flew in from eight different cities.

Plus is a remote-first company, and this was the first time that most of us got to meet one another in person, so it was very fun and very productive. We invest a lot of time and energy in trying to build a great remote work culture, but certain things are just hard to do over video. So during our offsite we focused on collaborative activities like brainstorming, small group breakouts, and discussing topics like company values and how to give and receive feedback.

We also made sure to schedule dinners and activities so people would be able to connect with one another in different 1:1 settings and create opportunities to have the lunchtime debates and hallway conversations that happen more frequently in an in-person work space.

Overall, it was a lot of work to plan the offsite, but we thought it was a great use of time and resources because we were able to spend time building relationships and collaborating on things that are challenging to do remotely.

If your team is thinking about planning an in-person offsite and want to see what we did and how we did it, here's the agenda for our offsite along with some color commentary on how we did it and what we learned for next time.


See the full agenda day by day here: 2022 Q2 Offsite Agenda

How did we plan it?

  • Our VP of Engineering, Prateek, took the lead on managing logistics (e.g., choosing a destination, booking the "house," writing a travel policy) and creating a draft agenda
  • As a leadership team, we outlined the core themes and topics for each day, and then we asked the team for feedback on the agenda and to volunteer to lead different sessions
  • Prior to the event itself, we walked through each person's session to make sure we were set up to have good discussions on each topic
  • For one of our weekly icebreakers, we asked the team what food/snack/beverage they would like to have a lifetime supply of, so we could stock the house accordingly 😄

What were some of the decisions we made along the way?

  • We chose to host the offsite in Chicago (even though no one on our team lives there) because there were direct flights for everyone
  • We decided to make this an "offsite" (80/20 focus on work/fun) vs. a "retreat" (20/80 focus on work/fun)
  • We booked an Airbnb instead of a hotel, so we could have common spaces for unplanned and unstructured interactions (but made sure everyone still got their own room and bathroom)

What were some of our favorite sessions and activities?

  • A brainstorm on how to approach longer-term technical challenges. Everyone on the team participated (not just engineers), and it was energizing to zoom out and think big about what's to come
  • A discussion about our culture and values. After months of working together, we had a lot of alignment on the key tenets of how we want to build this company and work with one another
  • Celebrating two of our team members' one year Plus anniversaries (check out Joe's one year reflections here), going to team dinners, a comedy show, and a Chicago scavenger hunt

What are some of the learnings for next time?

  • We had a pretty action-packed schedule, and it would be pretty tiring (both physically and socially/mentally) to do something like this every single quarter
  • Going forward, we're planning to try something in-person every quarter or two, but we will mix up the format throughout the year, e.g., an offsite, a retreat, and an optional co-working week in between
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