How to design a well-designed offsite

Helena Seo
Groupon Design Union
8 min readJun 28, 2018


UX Design at Groupon is an organizationally-centralized but geographically-distributed team. There’s one time of year when everyone in the team — designers, researchers and content strategists — come together for our annual spring offsite.

The offsite has provided the team great opportunities to learn new skills, expand creative thinking, and most importantly unify and strengthen the team. It’s been an annual tradition since 2013, and we feel very fortunate to be a part of the company who values and invests in team building.

Our team just had this year’s offsite for three nights in beautiful Monterey, CA, in early May. It had a successful turnout, scoring 4.86 out of 5 in overall satisfaction based on the internal post-event survey.

This article isn’t meant to be another chronological documentation of the event for the self-indulgent celebration. Rather, the goal is to share a few useful tips and ideas on how we were able to achieve a nearly perfect satisfaction score at the offsite with those of you who are also planning for a similar event in the future.

I find that designing an offsite somewhat similar to the UX design process. You need to understand main demographics first, empathize their pain points and interests, go through multiple rounds of diverging and converging, and finally deliver the most creative possible solution within constraints.

1. Get the logistical headache out of everyone’s way

Similarly to any personal trip, having to rent, drive or park a car can be one of the biggest logistical headaches during the team offsites. Specially when nearly 30 people are in motion all at once, there are likely more chances of unexpected unfortunate instances. Those instances can take fun and excitement away from the actual offsite event.

This year, we decided to avoid the issue by investing in a shuttle service: One shuttle taking the locals from the Palo Alto office and another one taking the travelers from San Jose airport. Nobody in the team had to drive, and we could get around downtown via Uber/Lyft easily once we were in Monterey.

2. Involve everyone in planning, but with a specific ownership assignment

The more ownership the team feels themselves, the more active engagement and participation there will be at the offsite. Instead of a top-down planning, we decided to take on a more autonomous approach this year and truly practice “team of the people, by the people, for the people.”

Each team member owned some part of planning and operated in a designated committee, whether it was about running a skill training, selecting a dinner venue, producing event schwag, coordinating transportation, etc. Slack was an effective tool for the specific committee discussions.

Because of the shared responsibility, no one was overly burdened by the planning task this year. Also, as there was genuine, shared ownership of the event, everyone sincerely cared for and contributed to the success of the offsite.

3. Leverage the internal talents to better everyone

You’d be amazed to know how much diverse talent and knowledge exist internally, and how great it is to learn from each other. These internal knowledge transfer can be sometimes more applicable and practical than learning from an expensive external speaker, because the training content is more contextual to the daily task at hand.

We recruited the trainers within the Design team for both technical and soft skills a couple of months in advance, and asked everyone in the team to sign up for the classes of their interest. The sufficient lead time provided the trainers enough time to prepare for the class materials, strategize the right interaction model with the trainees, and design the difficulty level properly.

In this year’s offsite, the technical trainings were all about prototyping in a tool of individual’s choice: Framer, After Effect and CSS. As our design team focuses more on innovation of micro interaction and effective collaboration with engineering team, enhancement of the prototyping skill becomes more critical across the board.

Soft-skill trainings had two breakout sessions: How to improve storytelling skill using user-centered case and how to understand nuances of working with data. Both sessions were designed to help the collaboration with the cross-functional teams and empower the design organization further.

These internal trainings enabled continuing Q&As and motivated each other to hone in skills further not only during the offsite but also the post-offsite.

4. Design one-of-a-kind activities through a creative spin

A few images may come to a mind when you picture a corporate offsite: A roundtable for introducing each person, an icebreaker game, a blindfold challenge, and if budget allows, perhaps a ropes course.

We didn’t do any of that in this year’s offsite. Instead, we considered how these activities can uniquely leverage our creativity as a cross-functional design team. Here are a few activity examples the team thoroughly enjoyed and therefore scored high in satisfaction:

A. Introduction of everyone via a trading card

Just for a background, each quarter, individuals in UX Design team are paired up with a “buddy” who they normally don’t work with. Buddies go through a few conversational activities to discover each other over the quarter, and then present each other in various forms at the end of the quarter. This activity has proven to an effective way to build a supporting system within the team and create a collaborative, friendship-based culture.

The outcome of this quarter’s buddy activity was a trading card. We used it as a way to introduce everyone in the team at the outset of the offsite. Everyone had such an interesting story to tell about his/her buddy creatively, and the session itself played a nice ice breaker as we were heading to the three-day eventful offsite.

(Credit for designing the buddy trading-card program goes to David Schnorr and Matt Hanson! Stay tuned for their upcoming article that’s dedicated to this particular program.)

B. Team building through building a boat — a real boat that floats!

We wanted to pick a unique team building activity that involves creative strategy and collaborative problem solving to reflect our team’s strength, and boat-making activity perfectly satisfied our goal. We worked with Adventure Associates to help facilitate this event.

We formed 6 teams, each with 4–5 team members. Every team was given art supplies and asked to design, engineer and construct a boat in 2 hours. After the construction, a sailing championship began and competition was on! Both teams of the fastest speed and the best aesthetics were awarded.

This activity truly attested to everyone’s creativity, craftsmanship, and collaboration. It was also amazing to see how quickly role delegation autonomously happened based on team member’s strength and skill set without an explicit instruction.

(Boat on the left: Winner of the speed category; Boat on the right: Winner of the aesthetics category)

C. Laptop-less design activity

Most of us spend enough hours on laptop everyday. So we tried to avoid activities that involved a laptop except for the technical skill training sessions.

Among many great activities, one of the most successful creative exercises was the block-art building led by our own Kevin Fox. Everyone was given Lego blocks and a grid template to build any design of their choice in 30 mins. Despite the extreme time pressure, the team was able to create an impressive collection of block arts. This was a great way to stretch our creative (and mathematical) muscle in a different way.

5. Leave some room for personalization

In the group of nearly 30 people, there’s a broad spectrum of personalities, lifestyle choices, and skill levels. We designed the offsite with a structured framework with mostly maximizing togetherness, but with flexibility in some activities such as yoga in the morning and social mingling at night.

Skill trainings were done in a variety of breakout sessions where each person could get focused training based on their interest.

We also collected everyone’s dietary restrictions and menu preferences in advance, so that the hotel could accommodate most needs appropriately.

6. Start and end strong with meaningful celebration

Start: Our event was kicked off with State of Union where the team’s major achievements over the past year were acknowledged. The achievements included not only the success of the products but also the improvement of the process and operations. It was a great way to commemorate the countless accomplishments together and witness the team’s visible growth over the year. And the celebration fueled the positive energy to the rest of the offsite.

End: After the long three days of offsite, people usually get very tired, and all activities tend to become a big blur. To end the event strong with something to remember by, we played a video capturing all moments of the offsite. A photo/videography committee was formed in advance to capture the moments throughout the event. The below is the team video — hope you enjoy!

(Video created by Soffee Yang)

Closing Thoughts

We became a stronger and more collaborative team after the offsite. I hope our learnings and tips will also help many teams lead a satisfying offsite event. If you have any other ideas about the team event planning, please share them in the comments section so we can learn from each other!

I’d also like to take an opportunity to give a big shout out to the awesome Groupon Design team (A.K.A. Design Union) for everyone’s amazing ownership and participation at this event. Also special thanks to Pratik Mall, Ling Hu, Tracy Ulin, Kevin Mendoza and Tae Kim for helping me with this article.


Helena Seo is a Director of Consumer Experience Design at Groupon. We’re hiring all levels of designer/design leaders and content strategists. Want to work with us? Browse our current job listings or learn more about us at Groupon Design Union.

P.S. — Thanks for reading! If you found value in this article, please clap!



Helena Seo
Groupon Design Union

Design leader, people manager and product strategist. Currently Head of Design at DoorDash.