# Use This Startup's Playbook for Running Impactful Virtual Offsites

Many team retreats have the tendency to leave participants feeling exhausted, sick of slide deck presentations and itching to get back to the emails that have been piling up in their absence—and virtual offsites add marathon Zoom sessions and interruptions at home to the mix.

## PLANNING: A FRAMEWORK TO SET INTENTIONS

As we settle into the new normal of working from home (or living from work as some have taken to calling it), all of a startup’s regular milestones now need to be conducted remotely: product launches, performance reviews, strategic planning sessions, board meetings, and so on. Offsites may have been paused or put off initially, but as many startups embrace remote-first policies and plan to stay out of the office for at least the rest of the year (or even well into 2021), there’s no reason to hold off any longer.

> Team retreats offer up a venue for discussing important topics, brainstorming new strategies and deepening relationships — activities that are more important than ever in a constantly changing world.

For Mellard and Wang, the first step is thinking deeply about what the team should experience. “I had these ideas and I knew what I wanted out of the offsite, but I didn't know how to get people through that experience necessarily. That’s where Mike came in,” says Mellard.

### Write chapters, not books

Wang’s approach to translating Mellard’s vision as CEO goes more than a few years back — and the inspiration comes from an unlikely source. “I went to Georgetown for undergrad, and the Jesuits’ focus on [cura personalis](https://college.georgetown.edu/discover/cura-personalis/?ref=review.firstround.com) — the idea of taking care of the whole person — was deeply formative,” he says.

“Big retreats are an easy way to convene a large group, but a bad way to facilitate connection.”

> If you take a first principles approach to designing your team offsite, what would you do differently? If you thought about your retreat like a 3-credit university course, what would your employee outcomes be?

#### Use this experience design framework:

With that broader philosophy in mind, Wang cautions against getting right down to the brass tacks of which session will go where. “Run through a framework of laying out your objectives and outcomes, design principles and program theme before you even start delving into the details of pulling together the actual schedule.”

### CRAFTING THE SCHEDULE:

The next step is to translate these outcomes, principles, and the overarching theme into the details of the event itself, taking on the session design. “Create checkpoints along the way,” says Wang.

### Play and wonder

“Surprise and joy seem absolutely critical to me right now,” says Mellard. “Our days are a monotonous meld and everything’s both stressful and blending together.”

Here’s a sampling of how they infused play and wonder into Sitka’s offsite agenda:

- **Send an interactive surprise.** “We sent everyone 'Regeneration kits' as curated packages in advance of the event, with instructions not to open beforehand."  
- **Get in costume.** “One of our employees is battling a terrible condition and has been quite sick, so I asked her if she were to plan a party, what would the theme be? And she said ‘Under the Sea.’ So that’s what we did.”  
- **Create something together.** “We held a cooking challenge on one of the evenings. We split into groups of three, creating breakout rooms on Zoom so each group could cook together live.”  
- **Schedule free space and play time.** “We held two ‘blank space’ happy hours across the four-day event without any formal agenda.”

### Inclusion of families:

“Inclusion of families was a top priority for me,” says Mellard. “Right now, kids are seeing their parents work up close, in a different way.”

Here’s what that looked like: “The cooking challenge night was open to family members. We also held a communal dinner one night, where everyone ordered takeout from a local restaurant and then hopped on Zoom, with families joining in.”

## EXECUTION: PRACTICAL TIPS

What follows are the tidbits Mellard and Wang found most impactful as they ran sessions during Sitka’s virtual offsite:

### Facilitation matters. Think cruise director, not train conductor.

“Founders and people leaders tasked with running the team offsite should consider bringing on an external facilitator.”

### Welcome white space and get comfortable with silence

“There’s a lot more coordination that has to happen virtually, it’s not as simple as posting the agenda on the whiteboard for everyone to see in the conference room.”

### Mix up mealtime.

“The biggest thing here is variety,” says Mellard. “Some days we did lunches on our own, giving everyone extended time to make it for themselves. Another day we had ‘open lunch tables,’ where you could choose who to virtually have lunch with.”

### Make sure the (virtual) show runs smoothly.

“Have a run-of-show document, down to each minute.”

## THE FOLLOW-THROUGH: SUSTAINING THE DRUMBEAT

“As the event took shape, we kept repeating one of our design principles: **Drum beats, not lightning bolts.** A drum beat is something you consistently return to.”

> If you don’t review the work product or revitalize the energy you had going until the next retreat, you’ve squandered the capital you invested.

Here’s a quick rundown of how that’s been working so far:

- **The Monday morning ritual**: “The morning ritual flex space from the offsite really resonated, so we’ve made an effort to work that into our regular cadence.”  
- **Sustained inclusion of families**: “We created a Sitka Littles program, which organizes activities for the kids of employees.”
- **Onboarding**: Overhauling our entire onboarding process to include entirely different materials and activities.

## TYING IT ALL TOGETHER:

“If you’ve never had a conversation that’s even approached vulnerable territory, maybe starting out with gratitude journaling would be too aggressive.”

Ultimately, the key takeaway from this experience is the importance of adapting your approach based on your unique team needs and dynamics. Creating space for connection and engagement remains essential, now more than ever.