How we made remote work

For almost 7 years we ran Simply Accessible. At our largest we were nearly 30 people, and our team was distributed remotely around the globe. Not everywhere, but a lot of different places, in a lot of different timezones. All across Canada and the United States, plus Scotland, England, Italy, Latvia, Australia, and the Philippines.

Remote might not be the best word for it, because that implies that there was a “home base” or “headquarters” and that some people worked away from that place.

The reality is that we all worked from home, and while the headquarters were technically in Ottawa where I live, it felt more like Hangouts or Zoom was actually our home base.

Here’s some of the things that we did to make working in a fully distributed team work for us. It wasn’t perfect, there were always things that didn’t go as planned, but those failures gave us the opportunity to learn and grow from those mistakes.

I look back on those days with great fondness. We shared both difficult and joyous times together in the environment we created. We actively looked to make sure we could find ways to engage everyone — even if they didn’t live in North America where most of the team lived. We aimed for inclusion and openness and trust in the team. We always aimed for better, and tried to figure out how to get there. We grew together as a team. We weren’t perfect. I sure as hell wasn’t perfect leading the company. But we certainly were connected, and there were some things that we did that just felt really, really right.

1. We recorded almost everything, because with a distributed team, there was always a good chance that someone would need to catch up later. We’d take notes too, and post those in Slack or JIRA, or wherever. But we almost always had a way to catch up for people that were unable to attend.
2. We aimed to work out in the open. We might have had 25 different people working on 3 or 4 different projects. With people ranging from the UK, Italy, and Latvia, to North America, to Australia and the Philippines, we had a LOT of timezones to cover. We needed to have people know the current state of work in progress. We needed to know what work was available so that people could independently grab the next thing to be done, and what was going to happen next on a project. Again, not perfect but doing our work in sprints and having all work represented in JIRA as stories (sometimes Scrum, sometimes Kanban, sometimes Scrumban) was critical.
3. We aimed to write documents in the open. Trust is important for every team. We made a working assumption that it’s that much more important for a team that doesn’t all get to work in the same space. So we tried to write any documents that we were working on out in the open. Client deliverables? Did it in a shared Google docs. Proposals for clients? Shared Google docs. Articles and blog posts? Shared Google docs. All shared for anyone in the company to see at any time. We hoped it would help build trust by being so open.
4. Video, by default. As I mentioned above, we did a LOT via Hangouts and Zoom. All of our meetings were using video conferencing of some sort. And video was on, by default. Having video on for meetings both small and large (ok, they were all small when you’re talking a scale of less than 30 people total), that was comforting to us. Many of us had ONLY met or worked together via video. I don’t think we even made “video on” a rule, or a mandate. I think we all just preferred to work that way. To see other people’s faces. Working remotely can be very lonely, so this way of connecting was very, very valuable. Sometimes people would leave video off, and that was ok. But for the most part, it was on, and it felt good.
5. We created opportunities to meet in person. I wish we had done more of this, but we had a company retreat twice (once in 2014 and once in 2016). This was an opportunity for us to all get together in person. We worked together. We ate together. We drank together. We played together. We also looked for opportunities to meet when we did on-site work for clients — training or otherwise. While remote was totally doable, it was special to have a chance to meet and connect in person.
6. We tried to create ways of celebrating together. How do you have a company party when everyone works at home? How do you make sure that everyone is included? We made sure we took the time at the holiday season at the end of the year to get together. To reflect together. To share time together — longer than our usual Friday get togethers. Those celebrations matter, and I wish we’d done more of those during the year. And not just for holidays. If I could do it again, I’d make sure we had a number of chances to celebrate successful projects together.
7. Hiring by video. Our entire hiring process was conducted over video. We interviewed people and we considered how comfortable they were with video in the interview process. It wasn’t the only thing we took into account, but it was definitely part of it. If people felt reluctant to turn video on, we weren’t sure they were a good fit for the culture that we were trying to cultivate because video was so important to us.
8. We created opportunities that were our equivalent to being in the same space. For our distributed team, there weren’t opportunities for us to “pass each other in the hall” or “sit together in the lounge and play foosbal.” We created other opportunities for us to get together. We had daily standups. We had a standing invitation every Friday for people to get together and not talk about work, but just talk about how everyone’s week went — good and bad. We tried to switch it up sometimes too — despite being a mostly North American team, I recall we did some of those get togethers in timezones that were more friendly to our team members in the UK or in European countries, or in Australia. I wish we’d done more of that.
9. We created a show & tell tradition. I don’t remember exactly how it started, but this was a chance to connect in different ways too. We created a show & tell time slot on our calendars. There was a pretty simple set of rules for this: you teach the team, or share with the team something that was NOT work-related. We’d fire up video and as many would connect as possible. We taught each other about our hobbies and passions. We learned about knitting, and famous amusement parks in Pennsylvania. We heard stories of ridiculous RV trips across the USA, and had a live tour of a centuries-old Scottish castle. We got to see and hear the horses hooves as horses thundered by in the opening race of Derby season in Louisville, Kentucky. I’m missing A LOT of show & tell events here, but this truly one of my favourite ways we grew together as a team.

I’m sure I’ll remember more things, but for now, that’s a good roundup of the things that we did that felt right.

These aren’t rules for remote work. This isn’t an analysis of remote workplaces. This is not a list of things that if you have a remote team you should immediately go and try to copy or implement. This is simply my observations of what worked for us. Some of these are pragmatic and focused on the work, and some are just fun and about relationships with our teammates. I’m hoping maybe that you might read this and try some of these things too.