Making Remote Work
Making Remote Work

Over 18 months ago I wrote Year Five, an experience report I never imagined I would write. I closed the blog entry by saying I look forward to writing about Year Six. A year and a half later, I'm still having a hard time deciding what (if anything) I should write. My writers block isn't the result the Remote Work experiment failing. Quite the opposite, the success of the Remote Work experiment has helped shape a team I'm very proud to be a part of, and yet I find myself unable to declare victory.

"How can you work effectively with remote teammates" has become the most common question I hear when meeting up with old colleagues for coffee. Clearly people are interested in the topic. At the same time, I prefer not to write about half-baked ideas (these days), thus my apprehension in documenting my approach.

This entry is an experience report, nothing more, nothing less. I'd be very skeptical of anyone providing recipes or best practices around remote work. Those working remotely today are breaking traditional workplace rules. Some are succeeding, most are failing, and I don't know of anyone with solid general advice. What follows are merely my observations.

My team became remote on accident. My boss and I were a 2 person co-located team in NYC, he quit, they gave me his job, and my best option to fill my previous role lived in Chicago. David Chelimsky was willing to be in NYC 2 weeks out of the month, and I was willing to be in Chicago 1 week out of the month. It was effectively co-location, and our team ran that way for a couple months.

Sometime in month three I started to feel like having David in NYC 2 weeks a month was unnecessary, and (surprisingly to me) he'd independently come to the same conclusion. From that point forward we alternated on traveling 1 week a month - thus we worked remotely for 3 weeks out of 4. We saw no drop off in our productivity or camaraderie, and traveling less definitely improved our overall happiness.  I'm not sure how it would have worked out if I'd been forced to try remote work; however, arriving there organically was surprisingly painless.

Eventually the team grew and DRW hired John Hume, who lives in Austin, Texas. I believe it's worth noting that we each lived in a different city. I've always believed that a team needs to either be completely remote or completely co-located. The team is up to 5 people at this point, and I've actively gone out of my way to ensure no two people work out of the same place on an ongoing basis.

When you join the team you'll have to start on a 6 month contract. The contract period gives both you and I the opportunity to figure out if you're a good fit. There are plenty of brilliant people who I wouldn't work with: I'm looking for people with compatible opinions on software who are able to flourish in the environment we've created.

Remote disagreements are hard to resolve. We can't get a beer and talk it out. I can't read your body language (or other subtle signs) and see something needs to change. Thus, it's not enough to be talented, you'll also need to be a philosophical match. The philosophical ideas are easy to agree on when everyone's looking to start a new endeavor, but best intentions don't always equal an ideal working environment. The 6 month contract ensures both parties know what we're getting into long before we discuss the idea of full time employment.

My team is stretched through various timezones, sometimes from London to Los Angeles. This leaves the options of work odd hours, or finding people who can take on larger tasks and don't require constant contact. My team chose to go the latter path, and we've found no notable impact on our ability to collaborate even when our hours overlap as little as 2 hours a day. This choice is another reason the 6 month contract is critical: some people want more than 2 hours of contact a day. That's neither good, nor bad, nor is it easy to predict. If someone ends up needing more contact than they find they're getting, it's better for all parties if everyone goes their separate way after 6 months.

I've found that my opinion on pair-programming and co-location is constantly evolving. In more than 2 years of working remotely, I've probably done less than 4 hours of remote pair-programming. I mention this because some people believe remote pair-programming is an essential ingredient to successful remote work. I am not one of those people.

That said, I try to see my teammates as often as is reasonable, and we do often pair-program when we are co-located. At this point, I see every team member quarterly, and the entire team spends a week together every 6 months. We've found this frequency to be a solid balance between keeping relationships strong and keeping travel to a minimum.

The above schedule works for ongoing collaboration; however, the beginning of a work relationship is almost the exact opposite. When a new contractor joins the team, they travel and co-locate as much as possible. A recent team member spent his first week in Austin, his second in Chicago, and his third in London. By the end of those 3 weeks he'd seen the codebase from 3 different perspectives and spent a week (mostly pairing) with every member of the (at that time, 4 person) team. That much travel is a high up-front cost, but it helps immensely with learning both the codebase and the team you'll be working with.

Communication is what I consider to be the hardest part of remote work. I haven't found an easy, general solution, thus I often find myself duplicating effort to ensure teammates can consume data in their preferred format. A few teammates prefer video chat each time we're on the phone, a few teammates despise video chat. A few teammates like the wiki as a backlog, a few haven't ever edited the wiki (as far as I know). Some prefer strict usage of email/chat/phone for async-unimportant/async-important/sync-urgent, others tend to use one of those 3 for all communication. There hasn't been one tool that I would recommend; instead I think it's much more valuable to note that people prefer different approaches, and it's the job of the team lead to communicate with the team members in the way that they prefer, not the other way around. The only rule I try to apply universally: I end as many conversations as I can with "is there anything I can do to make your life better". If you constantly ask that question, it should be (often painfully) obvious what you need to change to continue to improve things for the team as a whole.

The question of hardware often comes up as well, what should a company provide, what should an individual? My approach: take the cost of a 30" monitor, any laptop, a tablet, a smart phone, and anything else they'd want, then average it out over 2 years. I think you'll find the amount of money is so trivial that you'd be a fool not to buy them whatever they want. (and that you're company loses money every time you waste your time talking about such a small expenditure.)

That's more or less it. I would summarize it like so: I want to create a team that people want to be a part of for at least the next 10 years. That begins by finding people who are a great fit; not everyone will be, and we'll learn valuable lessons from those people as well. We start the relationship out right, spending many hours together getting to know each other and getting to know the ins & outs of the project. From that point on we'll see if your preferred working style (hours, communication needs, etc) fit well with the team. We'll already know if you'll be happy on the team long before either of us has to commit to any long term working relationship. From there, as long as I remember that I work for the team, not the other way around, everyone should continue to be happy and effective.

