Working Remotely

I’ve been fortunate over the past decade to have been able to, in various capacities, work from home—or work in place, as some like to call it. First as a freelancer, then Yahoo!, then again when I went to work at Xero, and now back to working for myself.

Shopify has been the exception to the rule in that time and while I tried to instill a culture of remote work, I don’t think I managed to move the needle much within the organization.

So, after all that time, what have I seen that works and doesn’t work? If I were to start my own company, would I allow remote workers? If I were to join another company, how would I foster an environment that encouraged remote work?

What works

With the hindsight that comes from experience, what made it work? For me, it was about being given a discrete task with few or no dependencies. That’s it in a nutshell.

When I was a freelancer, I worked with clients to determine the scope of work, was given the autonomy to do the work, and then delivered the work.

At Yahoo!, especially in the beginning, I had a defined role that didn’t require much communication with the team or teams at large. I would get design work and then build out the front-end based on those. Again, being given the autonomy and trust to build things as I felt they should be built meant that I had very few dependencies. There was very little that would slow down my ability to produce work. (Well, except dealing with my own distractions—something that has become more difficult of late.)

It was fun to hop into a conference call from South Africa. Or to have a co-worker contact me from the passenger seat of a car driving the coast of Italy. I’ve done conference talks from hotel rooms. I’ve done work meetings from coffee shops around the world.

What didn’t work

Not everything was peachy, though. At Yahoo!, I was placed into a managerial role. Managing a team remotely, for example, didn’t go so well. I needed to be in lots of meetings and if people didn’t log into the teleconference, I was left out of the loop. I didn’t really know how to manage a team and that training was never provided, nor was it requested.

In the early days of my time at Shopify, I tried to convince management that supporting remote workers would make us a better company. But I didn’t know how to go about making remote work for the company. As a result, the initiatives that were implemented just fizzled. Instead, each remote office was given tasks that allowed them to work more autonomously.

At Xero, my struggle was mostly in dealing with time zones. Living in a time zone 8 hours away meant that meetings often fell in the evenings when I had family commitments. As a result, I missed countless meetings. While my team never made mention of it, I felt increasingly out of the loop and ineffectual.

Would I Lead a Remote Team?

Given my experience, would I build and lead a remote team?

Yes.

Now that I have some experience behind me, I think I could make it work. To do so, here are some things I would do:

Have discrete tasks

Give people ownership over something and give them the autonomy to build that thing with little initial oversight. There are opportunities through code reviews, design reviews, and other exercises to ensure that people are on the right track. Otherwise, get out of their way.

Communicate in the open

When you have some people in an office and some people out of the office, it’s easy for some communication to be isolated. The team in the office might come to a conclusion and never communicate it outside of the room that decision was made.

For distributed teams, that’s awful. Communicate in the open. Every decision is documented. Find a place, be it Slack, GitHub, Trello, or wherever, and get the word out.

Fostering Remote in a Company

Considering my failures at Shopify, I’ve wondered how, if going into a new company, I could enable remote work. I think I would take a more grassroots approach. I’d implement it for my own team and then teach other teams how to duplicate what works.

Of course, that requires buy-in from the higher-ups to be given that freedom within your team. Basically, you’re the Guinea pig and you’ll need to hit the mark. Establishing trust will be very important.

Assuming you have an in-office team, you can still encourage remote work with baby steps and possibly without needing buy-in. Allow people to work from home or work when they travel. Create a communication process that works whether people are in the office or not. Once you’ve proven that it works on a small scale, you can go to management with a proven track record.

Room for Improvement

I feel that some of the tooling for remote teams could use improvement. I’ve had ideas for apps I’d like to build that could help fill the void. With a remote team, you lose spontaneity. You lose the ability to turn to a co-worker and ask a quick question. You lose the ability to jump up to a whiteboard and gesticulate wildly to explain your point.

Instead, we’re often dealing with poor connections, or laptops awkwardly pointed at half a whiteboard, struggling to read what people are writing through the glare of overhead lights. Or struggling to hear people in a crowded, noisy room.

Despite the downsides, I’m still bullish on remote work. I believe that getting to work from anywhere in the world that has a decent internet connection is one of the great advantages of our wonderful industry.

The future is already here, it’s just not a distributed workforce yet.