Organizing retreats for remote teams is so much fun.

Few years ago, I landed in Honolulu for a week-long retreat we had organized.

Flying 90+ people to Hawaï required months of planning and a crazy budget of $341,202.56 😱

Buffer team meeting in Hawaii, Jan 2016

I remember meeting a team member for the very first time and thinking  “I never realized he was so tall… I guess I’ve only ever seen him through Zoom!”,good times!

Today, with COVID, things look different. We can’t easily meet in person anymore, most get-togethers have been cancelled.

Yet remote teams still need to meet, unite and discuss. Here’s how 10 remote teams ran their virtual Retreats, despite the pandemic!

How the Microverse team felt about their 2020 retreat.

If you’d like to hear from the remote teams directly, here you go! Else, keep reading for my summary.

Setting the retreat tone & rhythm

As you get started, you’ll have to decide what type of team retreat you’d like to organise:

Offsites and team retreats often sit at one of two extremes: focused on strategy at the expense of relationships, or filled with forced-bordering-on-cheesy bonding activities.

The same holds true for virtual offsites, plus the added downsides of marathon-all day Zoom sessions where everyone’s glued to the monitor and stuck in their chairs — all while they’re trying to juggle their personal life, whether it’s interruptions from kids, pets or roommates at home.

- FirstRound Review.

You’ll need to understand which guiding principles you will be using. I found this approach by the Sitka team fascinating! See how much thought they have been giving here:

Retreat Preparation

Most teams mix synchronous and asynchronous time in their virtual retreats. Here’s the Microverse team “Rather than set strategy over 2 days of in-person workshops, this time we evolved our company strategy, objectives and key results over a two-week period before we met synchronously”.

Also, the Parabol team decided to “Limit video conferencing to 4 hours per day: for the sake of time zone differences and “Zoom fatigue” we kept our time together short and intentional”.

HelpScout gives us the perfect illustration of instructions for a hat-making activity that had both an asynchronous and real-time component:

A Retreat Apart: Planning Help Scout’s First Ever Remote Retreat

Small groups work wonder!

Balsamiq team members, singing away!

People connect better in smaller groups, especially when paired with random people. Here are some examples of activities that you could be doing in smaller groups, as suggested by remote teams:

  • Everyone records a video to give a tour of their own house or working space, like MTV Cribs.
  • Gift exchange: Set a price limit and assign everyone a different team member for a mystery gift exchange. Send to remote workers via international post.
  • QuizBreaker: Team members privately answer a set of questions. Afterwards, a quiz goes out where everyone tries to guess who asked what!
  • Virtual escape games are a really great option.
  • You could put team members in the spotlight and let them be the star in their own story. You’ll be surprised by everyone’s hidden talents.
  • Invite people from the outside to learn from them: it’s the perfect time to open your minds! What workshops or speakers would be inspiring for your team?

Of course, you can also think of opportunities to connect different teams and let people present their work to the entire company so everyone can learn about each other’s project. But remember...

“If your offsite consists of several days of teams just presenting slide decks with a few breaks peppered in between, something’s failed along the way.”

-FirstRound Review

Working with constraints.

An online event takes some preparation but it gives you a lot more options to work with. It’s interesting to also think that you may want to wait to discuss ideas until one month before the event, as predicting how we’d all feel in a few months might be impossible.

So, people can’t see one another. Gifts or home food delivery may be fun, here are some cool sleepers the team Bearer had delivered to their team members:

Thoughtful planning

Staying on time is hard for all teams, it’s especially hard when you’re having lots of fun and forget about the time. It is important to ensure that people get breaks. For instance, scheduling ‘bio-breaks’ to get water, use the washroom....

As a rule of thumb, it would be nice to keep almost everything “opt in.” In essence, you would communicate that everyone should do what they personally needed to recharge. Even if that means holding off for a session or two!

Here’s some great additional advice from the HelpScout team:

  • Invite people into the planning process
  • Lean into the weirdness — and video
  • Set expectations and get creative with your kick-off
  • Over-communicate the schedule and send lots of reminders
  • Keep time zones in mind
  • Support spontaneity. Be yourself and have fun with it!
  • Mix up real-time and asynchronous activities
The BRYTER team virtually got together!

Maintain the link, even post-retreat

During those tough times, maintaining a link feels key. Team building doesn’t stop on the last day of your virtual retreats. Here’s some inspiration from Hotjar that’s been doing some great team building exercises:

  • The “10 things about you” list - Team members share a list of 10 interesting facts about themselves: anything goes!
  • 15-minute coffee & learn sessions - The team takes turns delivering short presentations on something we do, something we know, or something we are.
  • 30-minute chatroulette - co-workers are randomly paired up to have a 30-minute chat.
  • Weekly ‘Gamejar’ gaming sessions - a dedicated social fun hour where team members come together to play online games
  • 60-minute Wednesday bonfire -  the entire team catches up or talks about interesting topics and personal growth.

Over to you now!

  • If you’d like to be inspired by even more amazing People Ops specialists and COO organizing retreats, check out our full database!
  • If you have questions, email me on rodolphe (at) remotive (dot) io or DM me on Twitter :)

PS: Another cool exercise I wanted to share that I would recommend everyone to try out:

Remotive helps you hire remote employees: Hire remotely today!

Remotive helps you hire remote employees: Hire remotely today!