We Moved Our In-Person Retreat Online. Here’s What Happened

Shogun was set to have an on-site retreat in Costa Rica in 2020.

Planning began earlier this year. The dates were set for mid-July, and the operations team started sharing details with the company at large in February. Near the end of that month, we sent information to staffers on how to book their flights through our travel portal.

And by the end of the first week of March, we pressed pause on everything.

You know what happened next: The novel coronavirus spread rapidly around the world. While we hammered out a companywide response plan, postponing the on-site retreat was next on the list.

Safety is paramount, and it was a no-brainer to scrap plans for an in-person event this year. But we also value connection time as a company; we’ve had a couple retreats in different countries throughout the years, and it’s always been a great opportunity to spend time together and get to know each other.

So, we decided to recreate the event the best we could — online.

purple illustration of coworkers in a Zoom video call

Going From an In-Person to Virtual Event: First Steps

Once our Shogun co-founders, Finbarr and Nick, gave us the go-ahead, planning commenced!

And... I felt very overwhelmed by the idea at first, to be completely honest.

I'm the people operations manager at Shogun. While I’ve organized in-person retreats before, this was the first online-only event I was tasked with planning. It was daunting to figure out where to start and how to organize it all. (Thank goodness I’m a yogi and know how to work through the panic with some deep breaths and meditation to clear my mind!)

I started the process by putting together a Miro board with ideas around a general theme, which really helped as a jumping-off point. From there, our eight-person leadership team offered feedback and we made revisions to the plan.

Getting Buy-In

Everyone agreed that some form of a virtual event was needed. But, there were extremely diverse opinions about what it should look like and what the goals should be. 

Essentially, the “why” was a little difficult to come to consensus on; we had never done a virtual conference before, so there was nothing to measure it against and no prior experience to build on. 

Some of the concerns we had were:

  • How can we be inclusive of everyone in a global company when people are spread out across different time zones?
  • What will the level of interest and participation be?
  • How can we find the right balance between professional and social events?

And, essentially: Is it worth it to trade valuable work time for these activities, or would it just feel like another thing to do?

Overall, we knew we couldn’t replicate the magic of what happens during an in-person retreat. And we didn’t want to set up expectations that our virtual event was in any way a replacement for that.  

Ultimately, after many iterations of what the week would look like, we decided on four key items we wanted to accomplish with the event.

We wanted to:

  1. Give people an opportunity to discuss how they were feeling around the recent news of our upcoming growth,
  2. Foster more social connections,
  3. Create some new rituals to improve transparency between departments and
  4. Reward people with some awesome swag and time off.  

So, we scaled back from a full week completely dedicated to events to a few optional activities each day, Monday through Wednesday, with two days off at the end of the week.

purple illustration of coworkers on a Zoom video call

Deciding on an Identity

Once we had our goals in place, we needed a name for the event.

Our creative technical support engineer, Charles, helped here: He brainstormed a few ideas and then the Ops team voted on their favorite one. We decided on Sho-up — a combination of our company name and the action of employees “showing up” virtually to hang out with team members and participate in our activities.

Then, it was on to the fun stuff: perks.

purple illustration of a backpack and dog wearing a hat

I put together a proposal of swag items, ran it by Rachael to get her feedback, and then presented it to Finbarr and Nick for their final approval.

All team members received the following:

  • A black TIMBUK2 backpack,
  • Copper Cow Coffee Thai iced tea and Vietnamese coffee, and
  • A bunch of Shogun-branded goodies, such as a tank top, coffee mug, socks and hat

Oh, and team members didn’t know they’d be getting these items — a big purple box showed up at their door with a note to hold off on opening it until the first day of the event!

Recruiting a Team

The project was primarily my responsibility to manage, but I enlisted help along the way: 

  • Rachael, our director of operations, was there as my sounding board throughout. Her input was extremely helpful. 
  • All members of our leadership team submitted ideas and feedback based on what they knew their teams needed. 
  • I roped in Chelsea, our UX researcher, to help with the breakout discussions. She was instrumental in helping us plan this activity with Miro! 
  • Lynsey, one of our support team members, designed graphics for our “Save the Date” and retreat agenda. 

Lastly, we had a whole troop of people who assisted with hosting duties during the event — they led the discussion groups, coffee chats, department presentations and skill-share talks. It was a true team effort!

Kicking Things Off

The event took place October 12-14, 2020. 

We held events at various times of the day to accommodate workers in different time zones. We encouraged people to participate, but attendance was optional. We also dedicated a special Slack channel to the Sho-up so employees could interact with one another about it throughout the week.

Because we decided to scale back the event to just a few days, Zoom worked out well. But, there are many new virtual conference platforms out there for larger-sized event planning. With the future of work moving toward a more remote/virtual model, it’s great to see so many remote-first solutions popping up!

purple illustration of a coworkers in a Zoom video call

The Reception

During and shortly after the event, feedback started rolling in. Thankfully, most of it was largely positive.

Here's what a few team members had to say about our first Sho-up:

chelsea myers Sho-up quote card
a purple and black illustration of anonymous survey feedback
jill nahajewski Sho-up quote card
a purple and black illustration of anonymous survey feedback

Now: Where do we go from here?

Looking Ahead to Future Events

Based on the feedback we’ve received about the Sho-up — via a combination of Slack, video calls and an anonymous Google survey — we absolutely want to continue doing virtual events, even when we can return to in-person off-sites.

As we grow our operations team, we’ll ideally be able to distribute the planning logistics across a few people. Because, real talk: Planning the Sho-up was extremely time-consuming, especially on top of my regular job responsibilities. Knowing how much time goes into something like this now, I’d definitely give ourselves a longer time horizon to plan!

Additionally, I’d like to gather input from leadership first before spending time putting together a proposed idea… maybe have that group meet with their teams and submit a few ideas and suggestions about how they’d like to participate. Then, using that input, create the vision.

Lastly, we’re looking to make some of the activities during Sho-up (department presentations, skill-shares, coffee chats and breakout discussions) ongoing. It would be nice to figure out a regular cadence and host these gatherings in smaller doses throughout the year.

All-in-all, the event was a big success. We'll see what the next gathering — whether in-person or online — brings.

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Tiffany Cagwin

Tiffany Cagwin is the people operations manager at Shogun. She's a yogi and remote-work advocate living in Syracuse, NY.