On Remote Working

Joshua Hynes
Stack Overflow Design
4 min readMay 27, 2016
Five desks. Five team members. Five different locations. From left to right: Indiana, Pennsylvania, England, France, and Poland.

Three years ago I was in-between jobs. As many product design positions are located in the Bay Area, this inevitably meant I found myself interviewing with a company there… many companies actually. And while I was intrigued with the opportunities, the people, and the area (to a degree); I wasn’t really interested moving across the country.

Higher housing prices, longer commutes, and less time with my family gave me pause. These are things which everyone in larger metro areas has to confront. What are you willing to put up with and what aren’t you? At that point in my life, with my wife in her third trimester, I wasn’t ready to deal with a lot.

I worked on a distributed team previously, so whenever I could I asked about the possibility of working remote. When I learned one company I was interviewing with had two remote engineers, I immediately asked if they were open to the possibility the person in this product design role also being remote. After discussing it internally, the company informed me that working remotely wasn’t an option.

In the end it worked out. I joined Stack Overflow, a company which carries the banner for being remote-friendly. As the second designer on the team, I’ve had a hand helping build the amazing design team we have today. A team distributed across 6 countries and 12 time zones.

In March 2016, a co-worker and I attended IXDA’s Interaction 16. The most common question we received concerned how did the design team make remote working… work. Sure developers work remotely, but people were intrigued how we were successful when so many haven’t been.

The more I think about this, the more it amazes me. There we were, at a conference discussing how designers need to think in scales, markets, networks, and systems. That we need to start thinking beyond mobile to sensors, wearables, and IoT devices. We were talking about what’s happening in the near-future; and yet teams are still utilizing a mode of working that’s been around for the last 100 years. The internet frees from the confines of geography, yet we continue to purposefully restrain ourselves to work only in specific areas.

You cannot warn about what a new technology will do to a society because the society has already made the shift. … Technology is only a facilitator. Society changes, and that change creates new needs. That is why the technology is brought in. The only way to stop technology would be to reverse the changes in the society.
Mark Kurlanksy, Paper: Paging Through History

This amazement isn’t new. I’ve heard it many times over the last few years. I wonder if we default to in-office teams because we think they’re easier. The idea of working remotely seems difficult. Conversations that could be had ad-hoc in-house now possibly can’t happen if the person is working on a different schedule as you. Instead of reading body language, now your left reading between the lines of chat messages, emails, and Google doc comments.

Yet have we romanticized the idea of working in-house? Do we really think moments of epiphany come by being in the same geographical location? Or that big ideas are born within whiteboard brainstorm sessions? Maybe that has happened for you, but I can’t remember a single time that has happened for me. Every solid idea that I’ve had came when I was able to get alone, work through the problem without distractions, and cultivate a solution. Working remotely provides me this ability more easily than when I’ve worked with in-house teams.

Every design team should consider remote working.

It would be disingenuous of me to say that remote working is easy. It isn’t. You have to work at it and your entire organization has to be oriented toward remote working. Technology has allowed this new form of working to form, but it’s still in its infancy and there are challenges. We do find it beneficial to get together as a team a couple times a year. These are not insurmountable issues, but they are challenges. We’re figuring this out as we go along.

There was a time when relocating was the only choice available to a potential employee. Yet not so today. Every design team should consider remote working. Yes, it’s different, and hard, and requires internal processes to change, and some people may not like it. But just because something’s different, doesn’t mean we should shy away from it.

This is the first of series of articles from the Stack Overflow Design team. We’re looking to cover topics such as how does a remote design team “war room” together, the importance of meetups, what does being a “remote-friendly” company even mean, what does a normal day look like, and how we hire remote designers. If you would like us to talk about something in particular, please email us design@stackoverflow.com.

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Joshua Hynes
Stack Overflow Design

Design Manager @ Dialpad. Formerly Stack Overflow. I love my family, design systems, music, and learning.