We moved our startup from an office to remote three years ago, here’s three lessons we learned along the way

It all started with “work from home Wednesdays” and well, as they say, the rest is history. There are a million articles about remote teams now that we’re all stuck inside so I’ll do my best to keep this short and not repeat what everyone else has been saying.

What I think is interesting about our journey to remote is that we really did it step-by-step. It all started when one of our engineers suggested “work from home Wednesdays,” which was an instant hit. Everyone was more productive across-the-board and we found people came to the office on Thursday more refreshed and ready to jam than ever before.

Over the next year this evolved from working from home one day a week to working from home three days a week. As a founder, we made a big shift in our mindset that I can never go back to. Rather than using “time in the office” as a KPI reflecting a hard working team member, we shifted to things like productivity and ability to work as a true team player.

We also quickly learned a hard lesson. One of our team members wasn’t happy, and they started poisoning the well. In the office this was harder to pick up on, but with more days working from home this became clear pretty quickly. It was a harsh reality to face, but a great lesson to learn. Someone who we thought was a team player, turned out to be a team disrupter, but in-person they played the game perfectly so it was hard to notice…once we went remote, it was clear as day.

And this leads me to what made us really pull the trigger on remote. Building an exceptional team.

While we were once geographically restricted, opening up our hiring process to the whole country, rather than just the city we lived in meant finding people who not only had the skills we were looking for, but who also matched the culture we were building.

We live in San Francisco, I f&#cking love this city…but it’s safe to say not everyone wants to live here, and not everyone loves it. The same is true for just about any city in the world. I know some people who love New York, other people who can’t stand it. One of my good friends moved to London and absolutely loves it, another moved there and six months later had to come back because he couldn’t spent another day there.

The reality is, everyone is different, and forcing someone to live somewhere they don’t want to live often means diminishing their happiness. Which brings me back to offices. Commuting also diminishes happiness and wastes time. We had an engineer that used to commute an hour each way to get to the office. When we started doing “work from home Wednesdays” the first thing he said is, “wow — my day is so different without the commute.”

The result was, he spent more time with his family, was less stressed, and got more done. At the same time, he was trying to ramp up his personal fitness scheduled and suddenly Wednesday became his go-to day for going to the gym. Now that we’re three years into working from home I can say it’s been a truly satisfying experience in so many ways. We’ve helped parents spend more time with their kids and families, hired people across the US that are insanely badass at what they do but wouldn’t move to SF in a million years, and laughed until we all cried more on Zoom than I ever thought possible.

Okay, so I know I said I was going to keep this short so let me get to the lessons learned. Putting together an article like this I really wanted to make sure what I share is actionable. So I’m going to narrow this down to three lessons that I think can be helpful for anyone trying to get into the remote work groove.

  1. Use Slack, but be deliberate about how it’s used — I think the mistake we made with Slack when we first went remote was to try to use it for everything. We quickly learned that yes — Slack is absolutely essential, but only if used correctly. First things first, we replaced all internal company emails with Slack, major win. Second, we made an unofficial rule, if you noticed yourself having a full-length back-and-forth conversation on Slack, move it to Zoom and talk through it. Third, talk publicly in channels as much as possible rather than sending a bunch of private messages to a handful fo people. Out of all of these, knowing when to move from Slack to Zoom took the longest to figure out but has also been the biggest efficiency and culture boost all wrapped into one.
  2. Duh — Zoom — we tried every single video conferencing solution on the planet. From WebEx to JoinMe, Google Hangouts to Skype Video. I like to say we discovered Zoom before it was cool, but the reality is it was already way cool once we discovered it. Zoom does work better than any other streaming service, period. The conversations feel more fluid and natural and it actually works. We still have just as many meetings as we did when we had our office, but we now do it over Zoom. I’m still a big believer in face-to-face communication. There’s something about seeing someone that really changes the dynamic and Zoom helped us make this happen, remotely.
  3. Weekly one-on-one’s — it’s even more important to check-in with people regularly when you’re a remote company. We’re all human, and you never know when someone ended up getting upset about something someone else said, or felt like they got the short end of the stick with a particular project, or maybe just felt like their voice wasn’t heard. I’ve actually found that one-on-one’s over Zoom are actually more effective than in-person. I think it might just be the fact that when you’re in-person, it’s a little bit more intimidating or scary to complain, but when you’re sitting in your sweatpants in your home office you might be just that much more emboldened to give someone a piece of your mind. Either way, it’s been really effective and has allowed us to course-correct and solve team issues much faster than we did when we were all in the office together.

I feel like I failed at making this a short article, but damn, I did my best! The reality is, every single day a dozen new articles are coming out from startups like ours that have been working from home for years. I felt like it was time to share a few things we’ve learned along the way because, if I was a founder who now suddenly had to bring my whole team remote, I’d want to learn as much as possible from those who did the same.

If people seem to like this, I’ll write more articles about remote work. If a few weeks from now this has zero or one clap, I’ll just let this sit out there in ether as just another article written about working remotely during one heck of a crazy time in human history where everyone suddenly had to go remote.

Either way, thanks for reading, and if you do like this, feel free to give a few claps. We’re all in this together and I couldn’t be more proud to be a part of a global community that is continuing to keep people employed and continue moving our economy forward. Onward and upwards! 🚀