Our Remote-First Team Meets In-Person for the First Time

by

Jean Yang

The last few months, many of the early-stage CEOs I’ve talked to have had one common question at the top of their minds: when to get the team together—and how.

Over the course of the pandemic, our team has moved to remote-first, but there remains one question: what should we do about our in-person get-togethers? It’s typical for remote-first teams to get together at some cadence. And for early-stage teams that are working and iterating so closely together, it’s slightly nuts that we’ve worked together this entire last year completely remotely.

Recently, after months of waiting to see what was safe, and more months of waiting for a week that worked with everybody’s schedules, we finally had our first in-person meeting! It took nontrivial finagling to figure out how to do it in a budget-friendly, COVID-safe way, so here’s a post about how it went down.

We intend for this post to be helpful for anyone trying to figure out how to get their team together safely during the pandemic.

Meeting the challenges of COVID times

Due to the pandemic and being distributed across the greater Bay Area and Midwest, our team had never even all met in person together! After everybody got vaccinated, we decided it was finally time to make it happen.

In order to plan our in-person get-together, we had the following big questions:

Where? There are two parts to this question. First, what should the overall geographic location be: the Bay Area, where more people live, or somewhere else, where lodging is cheaper? Second, given that we have no office, what’s the venue?
How long? Because we need part of the team to travel to all meet together, we can’t exactly meet for the afternoon. If we set a duration that’s too short, then we’ll have to meet again, which both costs money and increases COVID risk of the team. Set a duration that’s too long and it’s not productive by the end.

These were our constraints:

COVID safety. We wanted to make sure we protected the safety of individual team members while also being good citizens, in terms of being generally responsible about now spreading COVID around the country.
Preserving team productivity. Having too many people travel or having people travel for too long can be disruptive!
Getting enough time together. We wanted to make sure that we got enough time together to do both the work collaborations that being in person is better for, as well as catching up on months worth of in-person social activities.
Budget. We didn’t want to spend too much money! This is not easy, given Bay Area hotel rates. Also, conference rooms on sites like WeWork and LiquidSpace are running upwards of hundreds of dollars a day—and likely involve shared common spaces with other teams, something we didn’t desire to do during the pandemic.

Here’s what we ended up doing:

Venue and duration. We rented a live/work house in the South Bay, walking distance from downtown Mountain View, for four days. The location was optimized to both decrease air travel of the team and daily commute for local team members. The house cost in the low hundreds per night, far cheaper than what it would have cost to put up two people and additionally rent a conference room. The house made it possible to share common spaces (like the kitchen) only with each other, as well as to keep windows and doors open for ventilation.
Schedule. We spent the first three days working, with a couple of planned dinners together. The fourth day we set aside for social activities. We settled on mini golf ⛳, wine tasting 🍷, and a BBQ 🍔: all outdoors activities! (We had previously discussed curling as a top choice activity, but unfortunately curling in the Bay Area is temporarily closed.)
COVID safety. All of us were vaccinated, but the Delta variant had been rising, to the point where the Bay Area has mandated masking for businesses indoors. Our non-work activities, including dining, were all outside. After learning that at-home rapid tests are decently effective for determining if people are actively spreading COVID, I ordered BinaxNOW rapid antigen tests for us to take at the beginning of the week, but unfortunately due to shortages the tests did not arrive in time. If you're planning a similar off-site, I would recommend ordering these tests and ordering them early.

Here are a couple of purchases that turned out to be key:

Whiteboard. Some people on our team mentioned missing a whiteboard, so I bought a mobile whiteboard off Amazon. I was able to transport it in my car, but due to the width, it needs to get disassembled in order to fit.
Projector. It also seemed useful to be able to project things from our laptops, so I bought a cheap portable projector as well.

How our first in-person week went

Our first in-person week went surprisingly well! It turns out that everybody works “just like their videos.” Renting a house turned out to work extremely well at our team size. Being walking distance from downtown Mountain View also meant that we could take breaks by walking there for lunch, dinner, and the occasional tea/coffee break.

Meeting in-person was great for hashing out things that required in-depth discussion, especially those that were best done with a whiteboard and not a wiki document. The discussions were great for:

Asking the hard questions about what’s working and what we need to improve. It’s not that we don’t do this in our virtual office, but being in-person made it easier to have longer meetings. This allowed for more follow-up questions, like “How do we know this is true?” and “Is this really the best way to achieve the goal?” It’s not that we don’t have discussions in person, but the in-person discussions were longer and deeper.
Sorted out priorities and strategic focus for the next couple of months. Again, we’ve been doing this on video for the last year, but having the space to poke holes in the plans helped us come out with more solid plans.
Discussing how we want to grow the team. We spent an afternoon talking about who would be a good fit, figuring out how we want to hone our recruiting and interview process to improve our chances of finding such people, and how we should change our current processes to find these people better.

Being in-person was also great for getting to know each other! Again, it’s not that we don’t have social activities on video, but people only have so much patience for sitting in front of their screen at the end of a work day, even if it’s for something fun. It was only through spontaneous discussion, for instance, that we learned Mark has two owls that visit him in his backyard. 🦉🦉

An actual photo of the owls in Mark's back yard. By Tim Cooper.

Or, we may not have discovered that a key gap in our hiring strategy is that we haven’t been telling people we want to hire that we want to hire them. (See Mark’s Tweet here.)

Lessons for our remote-first future

Here are some observations from our in-person week:

The whiteboard was the most popular aspect of the entire week. Everybody said that even though they had missed having whiteboards, they didn’t realize just how much a whiteboard could facilitate discussions. Because the whiteboard required less structure than Notion, where we keep notes during video meetings, people felt that it was more conducive to discussion.
Longer discussions were good for hardening plans. While short, time-bounded meetings force plans to get made, longer, less-structured meetings give space for people to poke holes in the plans. Especially when we’re designing a product that’s never existed before, these discussions are crucial for making the product better!
In-person is good for focus. During our in-person meeting, people often put phones and laptops away to focus on the discussion, unlike in remote meetings, which are necessarily in front of a screen.
Video lag fatigue is real. In person, we were able to meet for days and days on end without people getting (too) worn out. People on our team said that the lag makes it way more tiring to have these discussions on video.
Doing passive activities together is good for team-building. Some the most interesting conversations I had with team members happened while driving, or while sitting around doing other things.

Here are some ideas for improving our remote work:

Find a way to bring in the whiteboard! Maybe it’s attaching a video camera to an actual whiteboard. Maybe it’s using a whiteboard app with a tablet. We need to keep experimenting!
Be deliberate about asking the hard questions. During our in-person week, we found it incredibly useful to ask the meeting-extending, discussion-inviting questions like, “What evidence do we have that this is really the best way to go?” While we don’t want to make a habit of blocking two hours for every meeting, it seems like a good idea to set aside time to have these kinds of discussions over video.
Cut down video lag. From experimenting with my own personal setup, I’ve discovered that wifi is significantly worse than ethernet connections when it comes to lag. I’m curious about how much improvement we can expect if everybody plugs into a good internet connection.
Designate some meetings to be high-attention. For some discussion meetings that involve the entire team, it may not be a bad idea to ask people to close other windows.
Sit together virtually. Since returning from our off-site, more of us have started co-working on video. So far, based on extremely few data points, it seems helpful for encouraging spontaneous conversations more so than sitting in separate virtual offices. We’ll see how this experiment goes!

We also learned that our virtual work setup is pretty productive. Nobody went home in despair about the loss of productivity from moving back to remote-first. While we can certainly do better on some of the interaction ergonomics, it was heartening to discover that our remote-first setup is working well.

What’s next?

We made a lot of plans to make our product better, so if you’re one of our users, you can expect improvements! (And if you’re not our user already, you should consider joining our beta.)

As for our team dynamics, we’re looking forward to having our next team meeting again in a few months, or at a later time that is responsible with respect to the pandemic situation. In the meantime, we’ll be implementing some of the lessons from our first in-person meeting. Stay tuned for more lessons.

We are hiring, so if we sound like a team you’d like to work with, we’d love to hear from you!

P.S. For those who are wondering: our whiteboard now lives, disassembled, in a storage locker along with the rest of our key office items.