Optimal Workshop on the road: How we’ve made it work remotely

Like many companies, at Optimal Workshop we offer flexible hours and the option to work from home on occasion. This means that people may have a late start to drop their children at daycare or school, take a flexible lunch break to fit in a gym session or spend the day out of the office in order to get through some work that requires extra focus. However, up until recently the company has had less experience with longer-term remote working. We currently only have one permanent remote staff member, Paddy, our customer success manager who is based in Dublin, Ireland.

Stepping into the remote unknown

Over the past year or so, we’ve had three employees work remotely for more extended periods of time while combining this with personal travel. Matt, our designer and front-end developer, spent the summer in Canada to take advantage of Whistler’s world-famous bike park. Ellery, our Salsa-dancing software developer spent a year traveling through Central and South America with his dance partner and fiancée, Amanda. And I’ve just returned from five months across seven countries and three time zones where, amongst other adventures, I was keen to put my foreign language skills into practice.

For all of us, it was our first experience of working remotely for such an extended period of time. Fortunately, we already work almost exclusively in the cloud across the company. GitHub, Google Suite, Trello, Intercom, InVision, Evernote and of course Optimal Workshop are some of the tools where we spend our time, and Slack is where the majority of office communication takes place. We also record and distribute key company presentations, including our weekly Friday release demos. This ensures that everyone is on the same page, whether they just happen to be off sick that day or are on the other side of the world.

From our remote locations, we worked on a range of projects including improving the process of adding members to team accounts, adding the ability to organize Reframer project tags by groups and colors and researching the challenges users face when analyzing OptimalSort results. Read on to learn about how we tackled the challenges we encountered, as well as the professional benefits that we each gained from the experience of working remotely.

Remote design and dirt trails

Matt on his evening commute (with laptop in his backpack) in Whistler.

When planning his trip to Whistler, Matt knew from the outset that he wanted to work from an office. It was important for him to have a physical distinction between work-life and home, in order to stay focused and productive. At the time, The Network Hub was the only public co-working space in the resort town. Fortunately Matt landed a workstation there which he shared with another member who worked after hours.

As British Columbia is almost a day behind our headquarters in New Zealand, Matt worked regular office hours but from Sunday to Thursday, rather than Monday to Friday, in order to align with the rest of the team back home. When the Wellington office came online, it was 2 p.m. local time in Whistler. This meant that there were three hours before the end of the day during which Matt could check in with colleagues in person to ask questions and make decisions. When 5 p.m. rolled around, the chance to hit the bike trails for a few runs each evening meant that he avoided the temptation for work to creep too long into the evening. The fact that he needed to clear the space for his afterhours deskmate also ensured he stuck to this schedule.

Matt acknowledges that it could be a challenge trying to make the most of connecting with colleagues in the last three hours of the day — sometimes a meeting would be scheduled too late or he wouldn’t get a response to a particular question before the end of the day. Saying that, he still found that he was productive and didn’t let these delays stop him achieving what he needed to do. Matt found that these experiences reinforced the need to take responsibility for his work in a way that he’d have otherwise taken for granted in an office environment: “Being remote forces you to be clearer as to what you need from others and in following up on things.”

Developing software through Central and South America

Ellery’s courtyard office in Antigua, Guatemala

In contrast, Ellery took a different approach during his year-long trip through nine Central and South American countries. Before leaving, he’d negotiated with his team to work staggered hours in order to be online for as much of the New Zealand work day as possible. Ellery’s partner, Amanda, also continued to work during their trip. Though the experience of working remotely was not so new for her, as she’s a product designer at Timely, where the entire company work remotely on a permanent basis. Amanda’s experience and that of the wider Timely team were no doubt invaluable in ensuring things ran smoothly during their trip.

In most of locations where Ellery and Amanda stayed, the staggered hours translated to 1 p.m. to 9 p.m. local time, although during the month that they spent in Uruguay this meant that they would be working up until 11 p.m. each night! Their later schedule meant that they’d usually work from their accommodation, using co-working spaces as a chance for a change of scene, rather than a permanent base.

Ellery found that there were distinct advantages to remote work in his role. As programming requires intense focus at times, working from a quiet and independent space helped him get into the zone. Ellery also admits that he tends to pace around when he’s thinking, which is fine in private, but can be a bit odd in an office! He managed the distinction between personal time and work time by keeping to a set routine and using different profiles (e.g., setting up both a personal and a work profile in Chrome) and devices (e.g., using a laptop for work and then a phone or tablet for browsing Facebook or watching TV) so that he wasn’t distracted during work hours, or inclined to work overtime.

The fact that Ellery was online for the majority of the New Zealand day and was always receptive to questions and available for meetings led many people in the team to remark that it felt like he’d never left. Ellery also shared some great recommendations with the wider team around keeping connected, call etiquette and managing your time while remote that I found particularly useful before setting off on my own remote working adventure.

Researching on the road and around the globe

Checking out the view from the office in Playa del Carmen, Mexico

As I spent the first few weeks of my trip in Central America, I initially adopted a similar schedule to Ellery. This allowed a few hours of exploration in the morning before retreating from the heat of the day to settle down for work in the afternoon through to the evening. In terms of keeping connected with the team, this schedule worked well — I even participated in portions of a design sprint during the first two weeks, following some of Jake Knapp’s recommendations on how to run a remote design sprint without going crazy.

However, for the next couple of months I was based in Europe, where the time difference meant that any crossover with the New Zealand work day was difficult, unless you are a complete night owl! As much of my focus was on attending and presenting at local events and learning more about our European customers through site visits, I shifted back to a regular work schedule but allowed for a couple key meetings in the late evening. This also opened up more opportunity to work from co-working spaces and to connect with others — the previous weeks of working from my accommodation had started to get a bit lonely! A month at the convivial but calm Parisian shared office Le Laptop, definitely reinforced that I’m best suited to the structure and stimulation of an office environment.

For the rest of my trip through Canada and the USA, I kept a similar schedule and split my time between interviewing customers on site and working from my accommodation or from co-working spaces, as this suited both what I needed to achieve and how I work most effectively. I set aside a few evenings each week to schedule time for check-ins via video calls. Similar to Matt, this meant that I had to be conscious of making the most of this time, being proactive and following up. As a researcher, a core part of my role is the conversations that I have with other team members around what I have learnt, so making the most of fewer contact hours was particularly important.

Keeping connected the Optimal way

Technology and tools aside, sometimes it’s the simple things that really help you feel connected from afar. A rather quirky thing that colleagues back in head office did while we were away was make up cardboard cut-outs of each remote staff member. These cut-outs would be brought along to meetings or just hang out around the office. They even showed up to our 10-year anniversary party in lieu of absent staff! It might sound silly, but having a likeness of someone in the room during meetings and standups really helps to remind you who is on the other end of call and ensures that they’re not forgotten or overlooked during the course of conversations.

Kelly, Matt, Priscila, Rebecca and Samantha show their faces at the 10-year anniversary party

Another initiative kicked off by our Discovery Lead, Kat, was the creation of a Slack channel called #pic_of_the_morning where any team member can share a snapshot of their current outlook or something they’ve been up to each morning. It’s great to have an outlet to share a little bit of your experience when you’re on the other side of the world and it’s really fascinating to see all the things that others get up to. On a recent trip to visit family in Japan, which included a few days working remotely, our designer Keisuke captured this amazing range of (rather complimentary) tofu found in a Japanese supermarket.

Tips for optimal remote working

There are a range of great resources on successful remote working, including 37signal’s Remote – Office not required and Toggl’s Out of Office to name just a couple. We tried out suggestions from others, such as GV’s advice for remote design sprints mentioned above and Trello’s commandment that when one person is on a video call, everyone is on a video call. While it might seem a bit weird at first, from a remote perspective it’s definitely much easier to stay engaged in the conversation when you can see each person’s face and hear everyone clearly!

To get you started, here are five more tips from our team’s recent remote adventures:

1. Be open and realistic (though flexible) about what kind of work environment and schedule is going to work for both you and your team.
2. You can’t over communicate. Be proactive in letting people know what you’re up to and what you need from them.
3. Use different devices (or at least profiles) to separate work time from personal time.
4. Be creative about how to include remote staff in whatever’s happening at home, and for remote staff – think about fun ways to share your experience with the rest of the team.
5. Use a ritual to disconnect at the end of the day. There’s no better way to end the day than getting outside for some fresh air and a chance to clear the head. Especially when your current location lets you end the day with an evening picnic in a Parisian park, a few downhill runs through the British Columbian mountains or a mojito on the roof terrace while watching a Mexican sunset.

If you’ve got remote working tips of your own, we’d love to hear them!