Organizing a Remote Offsite for 15 people in 4 Time Zones

Alice Default, Co-Founder + CEO at Double

Alice Default

CEO + Cofounder at Double

How Double's CEO planned a virtual team offsite

Since we founded Double two years ago, our team has always taken time every quarter to re-align on our vision. We take this opportunity to think about our next steps as a team to build a flexible assistant service for busy executives, to help them save time and stay focused.

As a small team, our weeks are intense and we’re heads down non-stop. Setting aside time to take a step back on a regular basis gives us the space we need to challenge our assumptions, think out of the box, re-invent delegation from the ground up, and deliver the best experience to our clients and doubles. Though intense, these quarterly sessions have pushed our different teams closer, made our vision clearer, and our processes stronger.

For the first time ever, we held this event 100% remotely in June. We usually fly people in so we can all be in one place, so we had to adjust the way we organized this offsite to accommodate team members in Roma, San Francisco, New York, and a few spots in between.

I will share our week illustrated in detail, what we learned along the way, and tips on how to make it work for your team. Shoutout to Google Ventures' Sprint and Alan's Product Strategy Sprint, from which some of these exercises were inspired.

Goals of the week

We have iterated countless times on the format for this event. However, our main goals have never changed:

  • Regroup as a team around our vision, take a step back from our day-to-day, and reflect on our past quarter to get better before the next one.
  • Build quarterly roadmaps for all teams using our collective knowledge and experience. We don't just sell software, we sell a full experience, so we build our roadmaps together to make sure that our product is able to support our operations and customer success teams with new features as well.
  • Spend time together in a different setting, mixing people who don't work together on a daily basis to build stronger ties and come up with innovative new ideas.

Schedule for the week

We usually schedule our planning sessions for 2 full days with everyone. Being remote this time, we decided to do 2-3 hours per day over a full week, with individual "homework" on some days. This is how we organized the week:

Monday

Goals of the day

  • Reflect on Q2
  • Realign on Double's vision
  • Share company goals for Q3

Icebreaker | ~20 min

The team knows that I love starting these types of meetings with a small icebreaker. They help get everyone awake, active, and participating. With everyone being remote, this exercise was even more important to me to get the energy going.

Retrospective | ~1h 30 min

The retrospective is our time to think about everything that went well and not so well in Q2 as a team. Everyone takes 10 minutes to write things they've liked, learned, lacked, or longed for in Q2 on post-its. We used Mural to do this remotely.

Remote-Offsite-Whiteboard-Retrospective


Our board at the end of the exercise

Double vision + Q3 company goals | 30 min

To ensure everyone is aligned and prepared for the days ahead, I took some time to re-share the company's vision as well as the company goals for the next year and the next quarter. At Double, our current focus is growth and figuring out our go-to-market strategy.

We ended the session with some homework due the next day. I asked the entire team to take some time by themselves to think of ideas that could impact each of our current levers and add them to a table in Notion. Each idea needed to have a clear title, a well-defined "Problem to solve," and a suggested solution.

Tuesday

Goals of the day

  • Start building our culture doc
  • Categorize all roadmap ideas as must-haves, to explore, to prioritize, and later
  • Decide which ideas to explore on Wednesday

Culture exercise | ~1h

While we started Double 2 years ago, we still hadn’t taken the time to properly define our culture. We decided this was the quarter to change that. As a first step towards determining the company we want to be, we wanted to get input from the entire team. We asked everyone to answer four questions in a Typeform by themselves. Between each question, we took a small break to share some answers in small groups.

Roadmap idea generation | 2h

For this exercise, we returned to the list of 60+ ideas we gathered from the team through our individual brainstorms on Monday. The goal was to review the ideas, build upon them, and organize them into four categories: must-have, to prioritize, to explore, and later.

At the end of the session, we had 15 ideas to prioritize, 8 to explore, 14 to save for later, and 26 must-haves. The 8 ideas to explore would be examined on Wednesday.

Remote-Offsite-Roadmap-Ideas


A view into the Notion board we used

Wednesday

Goals of the day

  • Collaborate with different team members
  • Explore ideas that required more solutions research
  • Identify which of those ideas should be prioritized for Q3
  • Have some fun!

Roadmap idea exploration | 3h

We split the team into four small teams (mixing engineers and designers with ops, customer success, and marketing) and assigned each team two ideas to explore. Each team was asked to read through their ideas and work together to design one solution to propose to the rest of the company. They also had to evaluate the Impact and Effort of the proposed solution. We used Mural once again to brainstorm and work remotely on the solutions.

Take a break 🕺 | 1h

During our offsites, we always take some time to hike, cook, and play together. Since this wasn't possible this time, we did a virtual escape game instead with SF-based company Reason, which we highly recommend.

Remote-Offsite-Culture-Activity


Offsite 2019 vs Offsite 2020

Thursday

Goals of the day

  • Present solutions from brainstorms to everyone
  • Get everything together for team leads to prioritize roadmaps

Brainstorm presentations | 2h

We all came back together to see what each team had come up with for their two ideas to explore. For each idea, we picked someone outside of the initial team that had worked on that idea to present it. They go through the sketches and explanations available, as well as the recommendation for Q3 in terms of impact and effort.

Roadmap prioritization | 1h

This exercise is done with team leads only. We came back to our table in Notion with all the categorized items and looked at the "Must-haves", "To prioritize", and "To explore" ideas. From the 8 ideas we had explored, we had 6 left with a good enough effort/impact ratio to be prioritized.

Friday

Goals of the day

  • Decide on action steps for main topics of the retrospective.

Retrospective action steps | 1h

We split into three teams to think about action steps for the two main topics that came out of the retrospective on Monday. Each team took some time to discuss before categorizing them as "Start doing", "Stop doing", or "Continue doing." As a full team we went over all the ideas and voted on our favorites.

Remote-Offsite-Next-Steps

Learnings

Here are a few learnings I'll keep in mind as I plan our next remote offsite:

  • Make sure that the rest of the week is as light as possible for everyone on the team. Even though it's "just" 3 hours per day, taking a step back, brainstorming, and prioritizing takes a lot of energy. Especially remotely, where staying focused is harder than usual.
  • Start preparing sooner, to allow more time for the team to brainstorm individually on the high-level goals (we had one afternoon only this time).
  • Take more time to research our brainstorms beforehand, to be able to base them on facts, like data, current processes, and user stories.

I hope these learnings, as well as our plan for the week, will be useful as you start preparing your next remote offsite or planning session with your team. If you've already planned one, I'd love to know how you did it.

If you’re interested in a more detailed version of our agenda and how I ran each exercise—from culture survey questions to how we chose presenters— email me for a copy at [email protected].

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