Applying design thinking to planning an offsite

Applying design thinking to planning an offsite

By Matthew Williams

With a design team of 26 people spread out through 5 continents, 14 countries, and 9 time zones, finding ways to make remote work effective is something we have worked hard to achieve through our meetings, interactions, and practices. But with 50% of our current team having never met each other in person due to starting during the Covid-19 pandemic, we knew there were certain collaborative and relationship pieces missing in our puzzle to create a welcoming and impactful team culture.

It’s a unique situation to spend hundreds, if not thousands of hours working closely with others and never spend time in person. But with most travel restrictions loosening in the countries where we all lived, we decided it was time to connect together as a team in person. With the high investment of time and resources to get us all into the same room, we decided to approach planning the offsite like any other design project to help ensure our time together would be well spent. Here was our approach.

Photo of the team meetup

Our first team offsite in 3 years | By Nikki Maller | CC BY-SA 4.0

Research: What did the team want out of an in-person offsite?

We knew that this offsite would be different than the past few, which were done remotely but we wanted to hear directly from the team. We sent out a short survey to collect opinions on these questions: What do you want to achieve by attending the team offsite, what concerns do you have about attending, and what type of theme should we explore together?

The responses about what we wanted to achieve at the offsite were unanimously centered around building stronger relationships with our colleagues:

“I’d love various opportunities to connect with people on the team and interact with them in ways I usually am not able to remotely”

“I hope we can feel even more connected with everyone on the team through inspiring conversations and learn more about and from my colleagues”.

Other key points we learned from the survey were that the team was interested in being playful and generative together to improve our collaboration as a team:

“I hope we don’t over plan in order to leave time for spontaneous moments together. Something as simple as playing games together could be an effective team-building exercise”

“I think it would be fun and engaging if we did activities that sparked meaningful conversations. I always like to explore things that I have in common (or not, and give room for discussion!”

A theme focused on systems thinking also began to emerge from the survey responses, which mapped closely to our team’s longer-term goals. It was also clear that we should approach this systems-thinking theme from a wide perspective to show the many different intersecting systems at play in our day-to-day lives and connect those to how they might influence our team and design system.

With a theme and direct input from the team on what they wanted to achieve, we were making progress and ready for the next step.

Exploration: Brainstorming to connect our goals and theme

We knew what the team wanted, but how do we get there? Our first step was to produce as many ideas as possible. Creating a range of ideas at the beginning of any project has always yielded a similar path of confusion > excitement > clarity for me, and this was the case even when designing an in-person experience. We brainstormed together as a group of design managers for a few weeks and made lists of possible presentations, activities, and games that could connect to our theme. We also made sure that each of us had dedicated time on our own to explore and refine our ideas to bring back to the group.

A twist: Hybrid meeting strategies

Every project has twists along the way and as we started to make progress and dive into the details we realized that a few of our team members weren’t going to be able to make it in person to the offsite (for various good reasons). We wanted to make sure that the experience felt natural to them and that they weren’t just “watching” others participate for a full workday. With a large range of time zones (14 hours!) separating the folks that couldn’t join in person, we came up with these approaches in an effort to include them in the offsite:

  • Asynchronous activities related to what we were doing in-person

  • Having a recording of each presentation that could be shared beforehand

  • Recreating the location-specific activities to work in other locations, or digitally

  • Creating a Slack channel with the folks joining remotely where they could collaborate together. We also made sure to have a couple of people who were attending in person to join to answer any questions or resolve any technical difficulties

  • Setting up the schedule so that there was one 2-hour meeting per day that accommodated all time zones, where remote attendees would join the in-person folks by video call

  • Multiple cameras and a microphone (including inexpensive solutions, such as using the mobile devices we had at hand) to make sure the remote participants could see and hear everyone

Photo of the team meetup

Having multiple cameras and passing around the microphone to help those joining remotely participate | By Matthew Williams | CC BY-SA 4.0

Planning: Bringing it all together

Once we felt like we knew how to support the folks joining remotely and had plenty of ideas, we began to group the ideas and create sub-themes for each day. The offsite was going to be 3 days, so we split the days among the managers on the team to begin the process of turning a rough outline into a detailed view of the day, including how our days would support those joining remotely. We also created one central Notion document where we put each day’s notes and agenda which helped connect the remote and in-person attendees as well as creating a central point for everyone to see what was happening.

Here are a few of the specific ways we connected our goals and theme:

Assigned “Coffee meet-ups”

One of our goals was for as many different individuals to have quality time with as many other people as possible. We did this by assigning everyone to a one-on-one meeting to start the day. Printed conversation starter cards and prompts that related to that day’s activities were given to allow folks to get to know each other while getting in the right mindset for the day’s events.

Photo of the team meetup

Printed conversation starter cards | By Carolyn Li-Madeo | CC BY-SA 4.0

Day 1: Connecting physical systems with digital systems.

With introductions and icebreakers to kick off the offsite, we all attended an immersive digital art exhibition (at L’ateliers des Lumieres). (The remote attendees did a related activity online). We divided into smaller groups and were tasked with finding a collection of physical objects that were connected in some way to the immersive art exhibit they’d just seen. Each group shared their findings with the larger group and the remote attendants at the end of the day, resulting in a dynamic conversation of varying opinions about the experience we’d all had. We realized that the opportunity to challenge and disagree with each other in a safe environment outside of our direct work really connected us in a deeper way, and was an important skill to bring back to our day-to-day work. That balance of creating space to disagree without a “falling out” is a difficult but worthwhile goal for team building.

Day 2: Seeing systems and defining emergent systems around us

In order to investigate the various systems that are required for a city to operate we split up into smaller groups, each with a specific activity related to systems thinking in a city which included an architecture tour, a sewer museum, a transportation exhibit, and a visit to a city garden and park. The folks participating remotely also went on various field trips in their local areas to map to the in-person activities. We came back together after and rearranged the groups so that there was a representative from each of the previous groups to collaboratively draw a map of the ‘perfect’ city (our remote participants built their own map together using Figma).

In our team meeting, we focused on prompts such as: How can you apply what you learned from your system of focus to improve the quality of life of your designed city? In what ways can connecting systems together improve or detract from their impacts?

This activity allowed everyone to connect in new ways, see the interaction of systems, and understand how those principles could apply to our team and mission.

Day 3: Playing with systems

On the final day, we created another opportunity for small groups to use design thinking to create together. Everyone received the same set of supplies and was tasked with creating a game and its corresponding instructions within a certain time frame. The groups then took turns to play one another’s games and give feedback, allowing the creators an opportunity to iterate and improve. This activity gave everyone a chance to see a different, more playful side of their co-workers while in the act of creation. It also showed that even with all of the groups starting with the same component that systems don’t constrain our possibilities but allow us to explore in a more effective way, mirroring how we could approach our day-to-day work.

Reflection: How to measure the effectiveness of an offsite

Immediately following the conclusion of our offsite, the team Slack channel was filled with photos from the week, notes about how great it was to get to know each other, and ideas and plans for the next time we would be able to meet in person. This showcased how our relationship as a team had really evolved. We also saw the spirit of the “coffee meet-ups” continue as there was a team-initiated Slack channel that assigned folks to meet virtually in a casual manner.

Even with this overwhelming feeling of positivity, we wanted to give attendees a safe space to give feedback and suggestions, we did this by sending a survey where we asked 3 questions to be graded on a scale of 1 through 5 (e.g. I have connected with folks who I’ve never met in order to build healthy working relationships), along with 3 open-ended questions (e.g. Is there anything you think could be improved upon for next time?) and a space for any other comments.

“The offsite was a great opportunity to get to know my colleagues and spend quality time with them. I feel much more connected to this amazing team”.

With positive grades and responses, along with a list of possible ways to improve next time, it was a fitting conclusion to using design thinking to plan an effective offsite.