How I Run My Virtual Offsites

I lead a 70-person group at a fully distributed company. Every quarter, I host a virtual offsite for my leadership team. Some have been amazing. Some have been terrible. Lately, I’ve had a number of folks asking me how I host my virtual offsites, so I figured it was time to summarize the learnings in one post!

In this post, you’ll find details on:

  • Why I run virtual offsites.
  • What tools I use.
  • How I set up my offsite schedule.
  • What session formats I’ve tried.
  • Mistakes that I’ve made, so you don’t have to.

Let’s get started!

Why host a virtual offsite?

It’s important to me that my leadership team meet quarterly to gain alignment and discuss big picture topics. But, I wasn’t convinced it had to be in-person.

In pre-pandemic times, my company encouraged two in-person meetups a year per employee. For my leads, this typically meant one meetup for our business unit (about 100+ people), and one meetup each of my leads would run for their specific team (a group of 5-20). On top of that, my leads were often traveling for conferences, customer meetings, and various learning opportunities.

While I knew a quarterly leadership offsite would be valuable, I didn’t want to add 4 additional trips per year for my very busy leads. Four leadership offsites per year means at least 8 additional travel days per year per person (not counting long-haul flights). Across my 10-person global leads group, this would sum up to approximately 80 work days spent traveling (packing, traveling, getting settled)… all on top of their regular obligations.

I was confident we could recreate the camaraderie and discussion virtually. We are a distributed team, after all!

I fully recognize that it’s not the same as getting together in-person. And yes, it means late nights or early mornings for some teammates (due to time zones). But, I knew it was a best setup for us. It meant we could get together regularly without introducing extra travel exhaustion. And, my leads didn’t need to be away from their families for our offsites.

From a recent team townhall!

What tools do you use for a virtual offsite?

The truth: it’s nothing fancy. We just use our regular, day-to-day communication tools. This means we can dive straight into the work without needing to learn new technologies. Here’s what we use…

Zoom: As a fully distributed team, we’ve used all sorts of video conferencing software over the years: Skype,, Google Hangouts, Slack Video, and Zoom. Once we settled on Zoom, it was transformational for our team. It was incredibly stable, had a clear “Brady Brunch” screen, included effortless screen sharing, and was very simple to spin up. We transitioned to Zoom a few years ago, and have never looked back.

Slack: We have also used all sorts of chat clients over the years, starting with IRC (holy steep learning curve), then to Skype, and now to Slack. My leads and I have a private Slack channel where we share updates, troubleshoot, and get support from each other. This “backchannel” has been critical in forming a team bond. During the offsite, this backchannel becomes our “offsite” channel.

Google Docs: At my company, we default to transparency… even when things are a work-in-progress. My leadership group has a single, “rolling” Google Doc for agenda-setting and collaborative real-time note taking for every meeting. For the virtual offsite, I create an agenda in Google Doc and share it for feedback about a week before the offsite. Then during the offsite, we rotate live note-taking in our Google Doc. (I also use Google Docs for my one-to-one meetings, see Mistake #6 on this post).

Other one-off tools: While not in every virtual offsite, here are some other tools we’ve used over the years for various virtual gatherings.

  • Trello: a structured way to share and organize ideas. One of the best uses of Trello during a virtual offsite was for a team prioritization exercise, where we ranked and categorized our priorities.
  • Mural: a collaborative art board that allows for collecting and reorganizing ideas.
  • TeamRetro: a structured virtual workshopping tool.
  • Google Slides – collaborative presentation making.
  • Unlock! – Yes, this is not a tool but rather a card-based escape room. Did I ask all teammates to order the same game, and did we play it virtually over Zoom? Yes. This was pretty involved but so, so fun. If you want to learn about how we set this up feel free to message me on Twitter and I’ll send you details.
  • A real whiteboard – So low tech! But, having a whiteboard behind you as you brainstorm ideas can be really helpful sometimes. I was able to do this by booking a conference room in my coworking space.

How do you set up your virtual offsite schedule?

First of all, you have to remember that Zoom fatigue is real. There is a maximum amount of Zoom time you can force on your offsite attendees before they glaze over.

Over the last few years, I’ve found that the ideal virtual workshop setup spans across 2-3 days, with no more than 5 hours of scheduled time, and includes lots of breaks.

For the globally distributed nature of my team, the ideal start time is 9am Eastern, which is barely late enough for west coast, and not too late for EMEA or APAC.

You’ll need to have a bit of attendance flexibility: You may not have west coast folks join for the start of the workshop, or maybe they’re audio-only for the first hour. You may not have APAC folks join you for the end of workshop.

For larger workshops, we’ve held sessions twice or taped them to accommodate schedules. For my 10-person group, we aren’t usually able to do that. Here’s a typical virtual offsite day for my leads group (all times Eastern):

  • Session 1: 9am to 10:30am
  • 15 minute break
  • Session 2: 10:45am to noon
  • 1 hour and 30 minute break
  • Session 3: 1:30pm to 3:30pm.

We typically run this schedule for two days, and then the third day can be a half day.

Across all of the offsites that I’ve run, I’ve done one thing consistently: kept the very first session entirely social. The way that I think about this is: when you arrive at a conference or offsite, you typically spend the first evening getting dinner or drinks together, and getting excited for the days ahead. I recreate this with a structured social session, where the only goal is to get to know each other, and bond as a team.

What formats have you used for your sessions?

While planning my first few virtual offsites, I found myself searching the internet for ideas and not finding many. How do I make sure this doesn’t turn into a 5-hour long, open ended Zoom meeting? We ended up experimenting with a mix of formats, or adapting things from in-person workshops that we run. Here are some formats that have worked well.

Red/Yellow/Green check-ins: This is something that my organization has learned from our Reboot workshops. At the start of a day or a session, we take a moment and each person goes around the room and says red/yellow/green on their ability to focus for this session. Example: “I’m a bit yellow today because my kids are being super noisy, but I’m hoping to be green once they go down for their nap.” It helps the team understand what’s going on with each individual.

Icebreakers: This is where everyone takes a turn and shares something about themselves. We’ve done everything from Two Truths and A Lie, to The Origin of My Name (this is a particularly fun one). During the pandemic, we had everyone take 5-10 minutes and either share photos from a recent vacation, or give us a tour of their office. It was a really fun way to “travel” virtually during the pandemic, and get to know your colleagues a bit better.

Breakout groups: This is where we take a particularly challenging topic, break it up into smaller chunks, and assign groups. Each group goes off in their own Zoom, and then comes back after 45 minutes to share their discussion and learnings. For these, we actually don’t use the Zoom Breakout room functionality, it’s too fussy — we just set up different rooms and then come back.

One-to-one coaching: I’ve found these to be pretty powerful workshops. We pair up leads who don’t normally work together, and give them about an hour to help each other solve one problem. The pair will spend half the time on brainstorming on Partner A’s problem, and then half the time on Partner B’s. It’s a great bonding exercise and may help unblock folks with fresh perspectives. At the end, everyone comes back and shares what they learned, which is a beneficial discussion on its own.

Townhall / Ask Me Anything: This is a good opportunity to bring in an executive leader into your small group setting, and encourage folks to bring questions they have. Questions sometimes turn into discussions, and that’s ok! It gets your team some visibility, and builds camaraderie between your team and the exec you invite.

From Sara Rosso’s blog post on the “How I Roll” workshop.

“How I Roll” Exercise: This is a fantastic visual exercise to do if your team is still forming. It helps teammates get to know each others’ personal preferences on a number of work-related topics. Early bird or night owl? Message me on Slack or give me a call? Once each teammate completes the plot, they can share out their choices. At the end of the exercise, you’ll get a pretty good diagram of your team’s natural tendencies. We’ve taken a screenshot of our diagram and shared it with the broader team as well. I learned about this exercise from my colleague Sara Rosso, who has a detailed blog post (including templates) on this workshop.

“How Might We” Exercise: I learned about this product exercise from my colleague Simon Wheatley. One teammate will walk the group through a customer journey, while everyone else jots down on post-its (or virtual Trello cards) ideas on “How Might We”… improve X. Afterward, you review all the cards and categorize/prioritize the list. Details on this exercise, along with many others, can be found in Google’s Design Sprint kit.

Tell me about the virtual offsite mistakes that you’ve made.

This is becoming a theme on my blog :) Here are some of the mistakes I’ve made, so that you can host can amazing virtual workshops right from the beginning.

Mistake #1: Packing too much into the schedule. In my early offsites, I tried to do too much, and tried to stretch out the days too long. Conversations need space to breathe. Humans need time to absorb content. Breaks are critical in ensuring you have a focused group.

Mistake #2: Not setting a clear agenda. On the other end of the spectrum, when I planned too little, the meetup was meandering and felt unproductive. Now, I always set one or two “big picture goals,” with structured sessions that support these goals.

Mistake #3: Not asking for feedback. My most successful workshops are ones where I brought my agenda to the weekly leads meeting and asked for feedback. Feedback helped me make sure the workshop topics were relevant and important to attendees.

Mistake #4: Not seeking a facilitator. When you’re leading a team and also running a workshop, your role can be confusing to the group – are you a conversation facilitator, or are you a participant? I’ve started noting in my agendas when I function as workshop facilitator, or when I function as a participant. In the future, I’d like to invite external facilitators so I can stay focused and present as a lead in the meeting.

Mistake #5: Not clearing your calendar. Every teammate has made this mistake and regretted it! Treat offsite days like at real conference day. Block off your calendar. For EMEA/APAC time zone folks, it can be tempting to work a full day then join the offsite in the evening. Don’t do this. Breaks are critical in ensuring you can bring 100% to the workshop.

Mistake #6: Keeping it internal-only. Seek out external speakers! This can bring a bit of inspiration and out-of-the-box thinking to your team. It can be someone in a different part of the company, or someone fully external. It helps make the offsite a bit more exciting and “different” feeling from a regular work day.

Wrapping Up

Now that you’ve run a successful offsite, here are a few things to do in closing.

Make sure to leave time at the end for a closing session. There will always be some light housekeeping items and todo items that need reiterating. Get that out of the way. Then do an actual “wrap up.” For me, we do a “teammate checkout,” which means we go around the room and everyone says how they’re doing and one thing they learned from the offsite. Sometimes I’ll jump in with a recap before we all close Zoom. The wrap up doesn’t need to be overly formal, but it’s important to mark the ending.

Screen cap of a recent internal summary.

Document the offsite for your team. As a lead, this is a good activity for you to do. It’s an opportunity for you to write a retrospective on how the offsite went and what discussions were particularly meaningful. You’ll appreciate these summaries over the years – I go back and reference my offsite recaps regularly.

Thank you for reading. This was my first post written fully on an iPad and the WordPress app (achievement unlocked)! If you found this useful, here are a few of my other posts on working with distributed teams.