Some reflections on planning all-company offsites

Lessons learned from doing two company-wide offsites a year: on designing intentional gatherings, making mistakes, and getting (hopefully) a little better at it every time

Brittany Jezouit
🏡 wfh
9 min readApr 3, 2024


Snapshots from an offsite in Austin, Texas.

My first day of work at Medium was at a company offsite in the Catskills, about two years ago. I was lucky that the start of my tenure at Medium lined up perfectly with the very first all-company gathering since the pandemic began. Since we’re a fully remote company, many Medium employees had worked at Medium for years without meeting any of their coworkers in real life.

I’m even luckier, now, to get to plan offsites for Medium as part of my job, alongside a thoughtful, talented team (shoutout to Brik Olson and Cameron Price, and everyone else who helps make these events happen). Last fall, we held our third all-company offsite, and we’re getting ready for another one in April. We’re fully committed to remaining a 100% remote company, and so, somewhat counterintuitively, these in-person gatherings are becoming critical to the way we work. While some other companies are quietly walking back remote work policies, we’re committing to our remote-first mindset — while recognizing that in-person time is hard to fully replace with time in a digital portal.

These all-company gatherings fill in the gaps of a fully-remote workplace — they help us align on a vision, build momentum, and learn to work together more effectively.

There’s no single way to plan an offsite, but now that I’ve done a few of these, I’m understanding more about what makes a uniquely Medium offsite. Here’s some informal reflections on what we’ve learned so far, and how we might do things differently now that we’ve had some experience.

Focus on human connection… but it’s okay if work *is* the way you connect

Medium’s mission is to help deepen our collective understanding of the world, so we think of the mission of our offsites as being to help deepen our understanding of each other. By spending quality in-person time together for two weeks a year, we hoped to bring back a sense of trust that would enhance how we worked for the rest of the year.

A lot of company offsites prioritize this by putting work aside for the week — essentially planning a week-long all-company vacation. Maybe this works for some folks, and I’m not against trying it out to see what impact it has. But I think it’s a missed opportunity to acknowledge that the work is the common thread that brings us all together. We all care about our work deeply, and it’s okay to embrace that as a way to connect with each other. My colleagues bring their full, creative selves to work, and it’s fun to see that energy in-person.

Set a clear purpose, but don’t over-engineer it

I read Priya Parker’s The Art of Gathering before we planned our offsite in Austin. One of Parker’s main points is: Every gathering should have a clear purpose — one that’s not generic or applicable to any other event. It should, as she says, “stick its neck out a little.” We’ve set purposes and intentions for each offsite, and having it written down is a helpful reference throughout the planning process. What we plan has to pass the purpose test. For example, if our purpose is to work on projects that don’t fit into our day-to-day structure, then a hackathon is a great fit for that purpose and a status meeting with our regular teams isn’t.

The Art of Gathering also spun me into a creative event-planning frenzy. I wanted to make the purpose unique!! and memorable!! I wanted to create an unforgettable experience for the team, for every moment to matter, for all of my colleagues to understand how each element of their experience fit into my vision for the week, each activity and communication painstakingly crafted to underscore a theme. The theme could be stories, with writing hours and reflections and arts and crafts and storytelling night, a version of The Moth, and a local tour that fit the theme, and a book exchange, and and and!! Wait, the theme could be the knowledge base, a riff on the way we talk about Medium itself internally, but *we* would be the knowledge base; we’d sleep in a college dorm in the off-season, attend lightning talks to learn from each other, close the week with some over-the-top graduation ceremony, with writers from the platform as our keynote speakers, a formal degree!! I was inspired; I was also, probably, somewhat exhausting.

Now, with every offsite, we seem to plan less. Some of this came from feedback from our post-offsite survey, a chorus of that was fun, but holy moly, we are so tired now. (Again, humans.) Keeping more space on the schedule for free time, a nap, or a run — normal human-y things people need — means saying no to the creative fever-dream, or at least to some of it.

I love Doist’s 20/30/50 rule for remote team retreats: 20% work, 30% activities, 50% free time. Even the work agenda is hard to plan ahead of time, because we don’t know what the big topic or need for the company will be until we’re closer to it. In future offsites, I think we’ll focus even more on what the activities and free time will look like, and ensuring there’s comfortable, communal space for people to gather, relax, and have serendipitous, unplanned conversations. (And, some time to take a nap.)

Meaningful moments from offsites past, clockwise from top left: Cozy fire pit time; an IRL hi-5 wall; a book swap; a somewhat impromptu karoake session.

Communicate, and communicate again, and again — but know that people might mostly ignore it until offsite time

The way we’ve done communication has evolved over the last few offsites. This round, we’ve got a process that feels good so far. It starts with a shared Google Doc with FAQ on travel and logistics questions, and a Slack channel dedicated to offsite questions and conversation. From there, we created a schedule outline and put that into a Google Doc, too — and replicated it as calendar blocks on everyone’s calendar. To connect the dots and make things extra find-able from phone, those docs are pinned to the Slack channel. If our design team has some extra free time before the offsite, we’ll turn these into something prettier; either way, we’ll probably print out one-pagers of schedules for everyone. We also know that everyone is busy leading up to the offsite, so the comms is built to be useful at the offsite — not assuming everyone has read every word beforehand. We also do short Loom walkthroughs of these docs, so that people can listen to the most important takeaways.

Good design or flashy landing pages are not the biggest priority for comms; functionality is! We don’t add any images or extra things to our communications, so that it’s easy to find what you’re looking for. As a company, we use Notion a lot, but unfortunately it’s harder to access from phones, so we use Google Docs here instead. One cool thing we’ve had at previous offsites is a text system that the event team can send out text messages in real time, like “dinner starting in 10 minutes!” It’s a helpful way to get information out, especially when folks are trying to avoid their computers to prioritize real-life interactions.

Offsites can be remote-friendly (and it doesn’t have to be annoying)

Sometimes, team members can’t make it in-person, for various reasons — travel conflicts, health issues, and family obligations can make it hard for everyone to commit to a week away from home. When folks can’t make it but wish they could, the FOMO is real. We’ve gotten better every time at including remote participants in offsites.

The first time we did this, the event organizers were mostly responsible for remote participation. That approach was a little messy. Over time, we’ve shifted the responsibility for including remote people to team members and leadership. For all-company sessions, we have a computer open with a Zoom room where we include the remote people, so that they can hear the intro talk, sessions, hackathon winner announcements, and even participate in the end-of-offsite toast before dinner. For team sessions, team leads include remote folks via Zoom, and in other creative ways. For me, the more fun parts of this have been figuring out ways to have remote folks participate in the fun aspects of the offsite, not just the work-focused sessions.

Some tips: Get some good microphones that you can pass around. Have at least two: one for the main speaker, and one to hand off to anyone else who talks. Attaching the mics to something helps (one of my favorite small memories of the last offsite: our VP of Content attaching microphones to hotel lotion bottles, so that his team had something more substantial to hold as they passed the mic around the table). Think about the experience of the remote folks — what are they seeing? Can they see? Can they hear? Move the computer around. Check in often.

Don’t plan a generic offsite, plan your team’s unique version of it

When we plan offsites, we think a lot about what makes Medium a special place to work. Previously, when we worked with an external event-planning company, we often heard that we were kind of a strange bunch. We’re perhaps a more mature company than many; people get more excited about late-night Werewolf games and nature walks than happy hours. (When we have happy hours, we hear a lot of appreciation for good mocktail options.) That’s part of the reason we took our offsite-planning in-house — we needed someone who really understood the needs of our team, our business, and our people.

Now, instead of looking to what other companies do at offsites, we just as often look inward for inspiration. We’ve even translated some of our remote all-company rituals to in-person versions. For example, one way we give each other shoutouts is through an internal Slackbot called hi5; at offsites, we’ve turned this into a physical IRL hi5 wall.

Medium is a mission-focused company. We don’t exist just to make money; the mission is the business. This shows up in how we spend money at offsites and how we spend our time where we’re there: do our priorities align with the mission? Does the schedule align with our purpose for the offsite — and more broadly, to our purpose as a company? Using these questions as guardrails helps us make each moment of the week more meaningful and impactful.

We’re getting ready to head into into our fourth offsite in a little over a week. I can’t wait to see my colleagues in-person — and to know that I’ll get to see them again in the fall, too. ❤

P.S., one of my goals in offsite-planning is to share more information and demystify this process for anyone who is interested in planning regular offsites for their team! There’s lots more I could add here, so maybe I’ll make this a regular series if there’s interest. If you have questions (or your own knowledge/lessons to share!), reach out or jump into the replies.