Working Remotely: 5 Lessons We Learned When We Made the Switch

After 4 years of working together in our office in NYC, went fully remote last March. Very few of us had ever worked in a remote environment before, and we knew there would be a steep learning curve. We did as much homework as we could ahead of time. We read every blog post we could find and we talked to friends who had experience working remotely. It was a months-long process, but we got there.

As many companies around the world close their offices due to the coronavirus outbreak, we’ve been sharing some of the lessons we’ve learned (check out these tips on how to make the transition to working remotely and some advice on how to work from home without childcare). Many companies are reimagining their existing policies in real-time, as we all face the possibility of this temporary set-up becoming the new normal. Even a year later, we’re still evolving our processes regularly, but here are some of the lessons we’ve learned along the way:

Transparency shares many core values with other companies: customer-obsession, teamwork, ownership, and empowerment. However, it quickly became apparent that transparency was going to be key to our success in the new remote work setting.

Now, let’s be real. We all think we’re transparent. It would be ridiculous to think otherwise! Transparency is an easy buzzword to add to a list of values, but it takes on new meaning when you are working remotely. Proactive transparency becomes critical to maintaining a team feel.

So we took a good hard look at how we could move an “open office setting” online. As a group, we retooled all of our processes to enable this goal of being transparent:

  • Decision-making — All non-private meetings are announced in a public Slack channel and notes are shared publicly after the meeting.
  • Individual work and roadblocks — Everyone, engineers and non-engineers, post a “standup” update in a public Slack channel every day.
  • Prioritization and partnering — We have a full team meeting on Monday mornings to share high-level projects for the week. We also discuss (and often negotiate!) tasks that will require help from another team member.


There’s no such thing as over-communicating (not to be confused with over-sharing 😀). We have a block of hours — 10 a.m. – 2 p.m. EDT — that everyone is guaranteed to be online and available, no matter where they are in the world. That means you can unapologetically reach out to anyone or set up a meeting in this timeframe without asking. This does NOT mean you should spend those four hours in meetings and it certainly doesn’t mean you can’t communicate outside of these hours. It just means there is a chunk of time where everyone is online and available. This also gives the team plenty of heads-down hours without meetings.

Equally important: We also communicate when we’ll be offline for any given amount of time (besides the obvious bathroom/snack breaks, that falls into the over-sharing category) and we promote it rather than discourage it. Think of it as the opposite of the old-fashioned “butts-in-seats mentality.” It’s helpful to know that Lauren is picking up her daughter from 2-3 p.m., and we can plan to chat again at 7 p.m. It’s helpful to know that Josh has an appointment and will be back after lunch so he doesn’t return to 70 pings from me. Communication builds trust.


Even though we’re in the meeting business, we are still mindful of practicing good meeting hygiene. This includes things like:

  • Announcing the meeting publicly
  • Set an agenda ahead of time with a goal
  • Share documents to review ahead of the meeting
  • Make sure someone is taking notes during the meeting to share afterward (and standardize documentation)
  • Organize the next steps and share broadly.

This all sounds a bit onerous and won’t apply to all kinds of meetings, so it’s important to make sure there’s flexibility in our approach. 

For example: If Slack conversations go back and forth more than a few times, we’ll jump on a video call to hash it out. Sometimes written communication can move a conversation backward when a 5-minute video chat can get it done.

Speaking of: As my colleague Ammon wrote in a recent blog post on work-from-home best practices — turn on your video! I know it’s super awkward to look at yourself and I certainly am guilty of leaving my video off at times. But I try to remind myself to get over it and give my colleagues that human interaction. It does help! After these sidebar conversations that grow out of a Slack thread, we’ll post a quick synopsis of the outcome of the conversation in the same thread.

Wild cards

Fun wild card traditions will crop up on their own based on your company’s culture — let it rip! We have a weekly Friday late afternoon Demo day with the full team meeting to show off what we’ve done over the past week. Many of us will crack a beer and engage in a virtual toast with each other, and one of our engineers Joe always plays his guitar for us to kick off the meeting while others join. We all enjoy Joe’s jams and look forward to it every week. Incorporate personal pieces of your lives into meetings and interactions. It helps keep everyone connected so embrace the wild card wackiness! 

Build consensus

For all the research we did, we intentionally decided to take a minimalist approach with our policies around working remotely. Instead of coming up with 1,000 different rules, we decided to focus on these core tenets to guide how our culture would evolve.

As you iterate on your own remote work policies, make sure to discuss and reach a consensus with your team. When even one person strays from these processes, they can easily crumble. Instead, focus on minimizing friction and overhead, and be willing to constantly evolve! is truthfully more productive now than ever before. If we can successfully execute working remotely after four years of staring at each other from across our desks, anyone can do it! Godspeed.