Planning a remote offsite

The team I support has traditionally done offsites twice a year. We are very distributed and find it useful to spend time together in the same location as a team at a planned cadence. This is important to get to know each other socially, plan work, and have some planning and strategy conversations. We usually do them in the summer as a team and the entire company does a large gathering in the winter. Due to Covid this year’s plan was delayed but after some thought we decided to do a “remote offsite”. I shared our experience via a Twitter thread and got questions around logistics so I’m sharing notes on what worked for us. A lot of these ideas came from the entire team, particularly my stellar staff team which is the managers and engineers who report directly to me.

Tip: The best offsites tend to be team efforts including the planning.

Goals and organizing principles

Offsites can have many different goals and in my experience I’ve found it’s easy to try to do too much with the shared time and cram a lot of different things into the agenda because of a fear of not using the time together efficiently enough. With this being a remote offsite there was a little less of this pressure since no one was traveling to be present for it. However, we were still asking a lot of people to collectively spend many hours of their time with this gathering. Focusing on a few goals seemed useful. I used the most pressing needs of the team as the lens to focus our goals. Our team has been growing rapidly over the last year and a lot of people are newer to the team and the company. On the work front, we already knew what we were working on for the rest of the year so a planning and strategy exercise wasn’t necessary. Given these, clarifying our goals and keeping them narrow made sense and we came up with:

  1. Sharing context on the work planned for the half

Having concrete narrow goals also had the additional benefits of helping me as the organizer because I was less stressed about what I would not get done.

Do not replicate in-person over Zoom

As an organizing principle it was also important to remember to not try to reuse elements of a successful in-person offsite and replicate them over Zoom. The most important one to discard was the idea of trying to have a series of meetings crammed over a few days. While planning an in-person off-site a key constraint is optimizing for travel and people being in the same location. With a remote offsite you can throw that constraint out and avoid Zoom fatigue in the process. Our offsite was spread over Tuesday to Thursday afternoons for 2–3 hours each over 2 weeks. We picked weeks that worked for the majority of the team via by informally polling people in the month before. Typically this is planned months in advance to accommodate for travel plans. Not everyone could make it all days and that tends to be the norm with these numbers and is ok. Due to the spread, most of the team could attend at least some sessions.

Agenda

With the goals and timeline in place, I crowd-sourced a rough agenda and then edited it to a shortlist of ideas with my staff. We then assigned DRIs (Directly Responsible Individuals) to each session via self-selection from the staff group or finding volunteers from the larger team. The DRIs then essentially planned the entire session they owned. Our agenda outline:

  1. Lightning talks where everyone shared their team’s plans for the upcoming half. Facilitated by Stanley, this allowed everyone to learn in an engaging way and went a long way towards achieving the shared context goal

Additional logistics details

  1. The team size at the time was 35 people, made up of 4 sub-teams spread across all US time zones and Tokyo. We planned around this with the previously mentioned shorter sessions, spread out over 2 weeks.

Things I would have liked to have done which I ran out of time for

  1. Facilitate a shared recognition exercise. In a previous offsite we facilitated a way for the team to share highlights and kudos for other team members. These were collected ahead of time and then shared anonymously with the team. It was a very popular exercise

Overall our first remote offsite as a team went pretty smoothly and while missing the energy of an in-person gathering I think we achieved the goals we set out with. It was definitely worth the time it took to set up and participate in which is probably the most useful metric.

Key lessons learned or reinforced

  • It is very important to plan enough to ensure that logistics are ironed out ahead of time. Zoom admin, pre-assigned note-takers, smooth hand-offs, scheduled breaks etc go a long way in helping stick to the agenda and reducing fatigue. It also goes a long way towards encouraging engagement and signalling that this is a good use of everyone’s time.

Hope this helps some folks. Happy remote offsite planning!