Simon St.Laurent - O'Reilly

Founded in 1978 and sporting a global workforce of more than 275 employees across multiple countries, technology publisher O'Reilly has long been a vanguard for remote-friendly work policies. Many of the company's editorial employees work from home, and even those who work out of their multiple offices are often given the freedom to work from home as necessary.

Pajamas talked to Simon St.Laurent, who has been with O'Reilly for over a decade about what it's like to work remotely and manage a distributed team.

This is part of a special two-part O'Reilly interview series. Be sure to also check out our interview with Simon's colleague, Jon Bruner.

What does O'Reilly do and what's your role there?

O'Reilly teaches people how to apply the latest and greatest computing technologies, and a lot more. Our mission is "spreading the knowledge of innovators," but a lot of getting this right is figuring out which innovations to cover, what kind of knowledge to share, and how best to share it. I focus on web technologies specifically, the pieces people need to build great sites and apps. After a dozen years focused on editing books, I'm now co-chairing our Fluent conference and working more on what we should cover than on creating it directly.

How much of O'Reilly's workforce telecommutes?

I don't actually know for the company overall. A lot of editorial folks have worked remotely historically, and a lot of people who work in our offices also work from home when appropriate. (We have multiple offices, which means that people are pretty used to dealing with remote communications even when they work in an office.)

You've been working remotely for closing in on two decades, with the majority of that time at O'Reilly. What initially drew you to remote work?

When I first started working at home, it was because I was shifting from writing books alongside normal employment to just writing. I wrote a lot, maybe too much, and that required a quiet place to concentrate, plus email and Fedex. When I joined O'Reilly, editing had similar demands, and they could see from my book output that I was capable of managing that from home. Working for a company from home has been different from contracting from home, but mostly easier. Working with the same people consistently spares me having the "oh, I work from home" conversation over and over!

How do you stay connected to everyone else on the team, including other remote employees and those working from an O'Reilly office?

A lot of it is email and web apps. Slack has been an especially useful recent addition for conversations that can happen in small bits, while Hangouts, other video conferencing, Skype, and the classic telephone also help. FedEx used to be really important when I was working on manuscripts, but FedEx has become a really occasional visit as most of it has shifted to electronic communications.

We do have some face-to-face meetings, at our offices, at our conferences, and at other places as needed. I've occasionally visited co-workers in their home offices and a few of them have seen mine. In-person can definitely be useful at key junctions, but all in-person all the time seems to have less value as the time increases.

What are the biggest challenges you face working remotely and how do you overcome them?

Starting out as a new employee was challenging. I came down to my office and it didn't quite seem like anything had changed, though it certainly had. It took me a while to meet people and get a better sense of people's personality. Email and phone calls could give me the basics, but it took a while before I really felt settled. I didn't actually meet the person who hired me until three months into my job. I'd visited the O'Reilly offices for interviews, but she also worked remotely, so we hadn't met. Fortunately it pretty much all went smoothly!

Meeting new co-workers can also be a challenge, though video calls have made that much easier. Last summer I hired a new employee, who's also working remotely, and I made sure that her first two days were in person at our offices so we could meet and she could meet a lot of her co-workers. That was definitely one of those key moments where in-person meetings make a lot of things go more smoothly.

In-person can definitely be useful at key junctions, but all in-person all the time seems to have less value as the time increases.

On a day-to-day basis, the challenges are pretty minor but occasionally annoying. My cable modem occasionally wants a vacation day or at least a slow day, so I'm very glad to have a telephone as backup. I'm also in the middle of massive renovations to my home office, as I hadn't changed it much in 15 years and really didn't like coming into it. I'm about halfway done, but past the dusty phase and into a phase where I can work comfortably in it.

The other challenge, of course, is kids. Mine are 4 and 6, a perfect age for combining loud with not quite getting the need for quiet at specific times. They seem to be getting better about it lately, though. Well, except my daughter just quietly looked in on a video call. (We also have roosters who somehow crow a lot more during conference calls.)

Why do you think O'Reilly hires so many remote employees? What benefits has it provided the company?

Mostly I think we do it because it helps us find great people. Editorial work is also a bit unique, in that it typically requires a lot of focus, so control over an environment helps. While editors (and salespeople) need to talk with people inside the company, a vast amount of their conversation is with people outside of the company, all over the world. That also makes distribution easier.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

I'm not sure there's a single most important thing. Building trust can be harder for a distributed team, and trust makes everything easier. Keeping channels of communication as open as possible is also key, but figuring out "as possible" has its own challenges. News "from the home office" is much rarer, and seems more important, but it can also be fun to sort out what matters most without context.

In the end, I guess building a culture of communication is the key, but that has a lot of parts.

Has building a cohesive company culture been difficult for O'Reilly? How are remote employees factored into the culture?

O'Reilly had multiple 'main' offices early on, and then added international offices to that and a few more offices (through acquisitions) as well. Remote layers on to that pretty well, and has been a part of the company long before I got here. The company culture comes more from what we're creating than from being in the offices. That may make it easier.

You supervise two other people who are in other locations. Is that difficult? How do you make that relationship work across geography?

Conveniently, we're in the same time zone, which makes it saner. It's a mix of regularly scheduled one-on-one calls, a few group calls, and occasional in-person meetings. So far, so good, though it's only been about nine months so far!

It also helps that one of the people in this core group works in our Cambridge office, so that gives our group a connection to the office. Our larger group includes a lot of people in the Sebastopol office, which also keeps us connected.

Building trust can be harder for a distributed team, and trust makes everything easier.

What are some of the benchmarks you use to make sure your team is in a good place, both mentally and operationally?

A lot of asking, mostly. I also explicitly ask people to stop me if my ideas push into bad places. Again, I haven't had enough time to tell if that works, but so far we seem to have stayed on the happier side.

Describe your personal work environment.

I work in a 10x12 room that's part office and part pantry. I'm in the middle of rebuilding it, which has been complicated, but finally sorting out. For years I've been surrounded by cans and jars as well as books and computers, but I'm finally making it a place I actually want to go. By the end of the year, it should all be settled. A cable modem and wifi plus a company-issued laptop are the tech key components.

How do you manage work/life balance when working from your home?

Mostly I try to keep work within work hours or close to it, though every now and then work hours shift or flex. Having kids who stop by to ask if I'm done working is definitely helpful as well!

How do you keep distractions to a minimum? How do you personally measure efficiency?

Most of the distractions I have come from things that would be distracting whether or not I was at home or in the office. Twitter, Facebook, and RSS feeds are great for keeping up with where the tech world is going, but are perhaps too enjoyably noisy. I cut myself off from television and video games a few years ago, so that helps a lot too.

Measuring efficiency is difficult. In practice, I measure my to-do list and my overwhelm level. That isn't strictly connected to efficiency, because projects pop up and disappear for a lot of reasons. I definitely feel it when I'm apologizing for not getting back to someone quickly enough, and trying to avoid that situation helps a lot.

What are some of the tools you couldn't live without as a remote company?

Email remains a key foundation, though I'd like to find more structured approaches for a lot of those conversations. Audio and video connections, whether phones, Skype, Hangouts, or videos remain key. Slack is definitely growing in importance -- I could replace it with IRC and some other pieces if I had to, but I wouldn't want to.

What advice would you give to a company heading down the remote working path?

Talk a lot, and not just on email. Noise can get annoying, but silence is a bigger problem. I definitely think that at least occasional face-to-face meetings make life much easier, but over time you'll develop a sense of which communications form is best for which kind of conversation.

I wasn't at O'Reilly when the remote working path was first starting, so I can't really explain how we started down that path, but remote work doesn't seem that complicated to me for the vast majority of project types. Try it, expect some discomfort at the beginning, and see how it goes!

Josh Catone
Josh has been the Content & Community Manager at feedly, the Executive Director of Editorial Projects at Mashable, the Lead Writer at ReadWrite, and the Lead Blogger at SitePoint.