A virtual offsite meeting? Quicken visited Bora Bora

Even the most passionate advocates of remote work that I’ve spoken to miss in-person gatherings, particularly larger summit-style meetings in which a working group or department gets together and spends several focused days working through an annual plan, major product launch, or other key initiative that requires team brainpower. Like most, I’ve tried various techniques with my teams to replicate elements of the traditional offsite, from Zoom or Teams backgrounds, to virtual cocktail nights and team dinners, with varying degrees of success. I thought I’d heard them all, until I had a chance to speak with software company Quicken’s VP of Marketing, Linda Itskovitz.

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Itskovitz created a virtual offsite meeting for her marketing team in Bora Bora, a location the team picked after voting from a variety of options, just as they’d done in the past when picking a location for their in-person off-sites. “Talk about it like you’re really going,” she suggested, and in that vein she and her team acted like they were executing an offsite meeting with everything from travel dates, to selecting a hotel and providing a hotel map with room assignments for participants and guest speakers. A packing list was provided, and as one might expect, suggested meeting attire was sunglasses and shades. Participants even set out-of-office notifications, allowing them to focus completely on the ten hours of meetings scheduled over the course of two days.

In advance of the meeting, each participant and guest speaker received a care package with everything from themed snacks, ingredients for cocktails, hula hoops, and an inflatable pool complete with a shark for themed elements of the meeting. The various packages were not to be opened until the appointed time during the two-day meeting, creating an element of excitement and surprise. They were also intentional: “We wanted to make it more than just Zoom,” Itskovitz said, and items like the hula hoop were not just for fun, but provided the perfect excuse to get participants out of their chairs and moving, to break up the monotony of sitting for an extended Zoom session.

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“Be a little crazy and have a big imagination,” Itskovitz suggested, as she shared that rather than a traditional kickoff rife with PowerPoint slides, the team “met at the airport,” with each team member applying an airport-themed virtual background, and enjoying a tropical cocktail for the start of the offsite. Team members were even provided DoorDash credits, which avoided lost time for participants to prepare meals, and helped drive home the feeling that they were at a real offsite, with great food and snacks.

“This cost us some money,” she said, and she admitted she received a raised eyebrow or two when requesting funding for a “virtual” summit that some of her colleagues initially perceived as being a zero-cost extended Zoom meeting. However, the results of all the effort were surprising. As she would do after a traditional offsite, Itzkovitz polled participants and asked for feedback. Most key metrics on outcomes and engagement were actually higher than traditional offsites, and one commenter even noted that “I really felt like I was in an offsite!”

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Creating an immersive experience was key to the success of the virtual offsite; however, technology also played a role. Itskovitz emphasized the importance of using the capabilities of your meeting tools, highlighting Zoom’s ability to create breakout sessions and quick polls as heavily utilized features. She also sang the praises of collaboration tools, in Quicken’s case, Google Docs. “The ability to all collaborate on the same document was a game changer,” Itskovitz said, highlighting the importance of spending some time familiarizing yourself with the functions of tools you might take for granted, while missing key feature sets. Whether your teams are invested in the Microsoft 365 or Google Ecosystem, both have extensive collaboration tools that allow your entire team to live-edit documents, and even annotate and draw with a touchscreen laptop or tablet.

Toward the end of the conversation, I asked Itskovitz a question that’s always on my mind when discussing the new habits of virtual working sparked by COVID: Would she do a virtual offsite again if an in-person option were feasible? “I love to travel,” she said, “but I could easily see one big in-person session each year, complemented by a mid-year virtual summit.”

In an age when we’re all experimenting with how to be productive and foster and maintain team and company culture, a virtual summit might be a great arrow for your quiver. Follow Itskovitz’s advice to “be a little crazy and have a big imagination,” and you just might create an experience that your team loves and that generates much higher quality outcomes than a regular marathon of videoconferences.

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