We Tried Building a Remote Team and It Sucked

Although I disagree with the overall sentiment of the article (remote working doesn't work for generalists). I commend the author for at least trying remote work (especially as a YC company, an organization that openly discourages remote work).

Full disclosure, I work remotely and it's by far the best decision I've ever made in my entire life.

So to address a few points. Collaboration to me is when a group of people, at least two, are working on a project together. As a designer this is one of the core aspects of my job. I'm constantly working on things with engineers, founders and marketing people. Therefore I feel that I have a solid idea of what it takes to collaborate efficiently.

At my previous job, that was location dictated, collaboration typically took place over chat. We did have meetings to go over larger ideas and aspects of the project, but typically critiques, pair programming, decision making all took place over chat. Even though we were in the same room we made it a point to communicate over chat because one: you need to respect my space and not interrupt me just because we're in the same room and two: we have a transcript so we can reference it later.

When I decided to leave that job as a developer and pursue a career in design I decided that I would look for remote work only. I firmly believed that everything I did on a daily basis in a single location could be done remotely.

The biggest point I want to make in this post is that tools are essentially irrelevant. What matters most is the management of people on remote teams. When you hire remote employees they need to be both self managing and self motivating. You need to make them aware that collaboration on a remote team is what each individual member puts into it. If they aren't documenting their work each day, if they aren't participating in daily scrums, if they aren't contributing to chats, if they aren't volunteering to review PRs, etc. it's just not going to work out.

For me, and many of the folks I work with, remote work is about freedom. The freedom to build your own schedule. The freedom to work on something early in the morning or late at night, in the comfort of your own home. The freedom to walk to a coffee shop and work from there. The freedom to forgo that commute. The freedom to be more productive. The freedom to spend more time with your family and loved ones. The freedom to just build great products without the hassle of office politics.

It sounds to me like you expected managing remotely to be exactly the same as managing locally. You expected to be able to gauge the morale of the team, to know what people though of the groups future, etc without having to actually DO anything. When working with people locally, you at least get the impression that you understand these things from general interactions. You are wrong, of course, as your intuition is just as terrible as everyone elses, but you at least get the feeling that you know the situation.

Of course managing remotely is different from managing locally. Coding, and actually being a productive knowledge worker, however, really isn't. Luckily, managers already make a large multiple more than most others in the organization, so asking them to adapt and work harder to accomplish their responsibilities should be less of a big deal than dumping that kind of thing on lower level employees who area already generating far more value for the company than they're being paid for.

edit: Oh, and brainstorming is a terrible waste of everyones time and is worse than a total lack of it. Multiple studies have been done and show that brainstorming results in groups taking far worse actions than if they use other methods of coming up with solutions.

In my last job, we had three main hubs and each hub had offshoots. So it was possible that every person on a project was working in a different location or they could all be in the same office. We did a lot of military contracting, and as a result, some work could only be done on-base; otherwise, we were allowed to choose where we worked.

In otherwords, it was a wonderful mix of everyone in the same office, remote teams, and working from home. Based on this, I learned I really prefer having semi-regular meetings in person (things like kick-offs and 6-month project retreat weeks), regular tele-cons (weekly all-project-hands), and the rest of the time I was able to work on my own from where ever felt the most productive that morning. On those days non-synchronous email communication worked splendidly. There were co-workers who really preferred only ever working in the same location as the rest of their team, so we structured teams that met that preference. There were other co-workers that were perfectly happy with completely remote work (in fact, I never met, face-to-face, three of my regular co-workers).

By and large, it really did boil down to preferences, although I did note that my co-workers that preferred in-person projects were the ones most likely to interrupt me - and be completely oblivious to the fact that they were interrupting me! My remote coworkers were much less likely to interrupt me, check to see if it was a good time when they did, and apologize for the interruption.

Seems that StatusPage.io is not either using anything worth to mention for "whiteboard simulator". So here is my shameless plug of the project that I work with.

Our solution for "whiteboard simulator" part is http://sketchboard.io that lets team sketch structural diagrams together in real-time.

It is not the same thing as working on a same room locally and use whiteboard since locally you can communicate a lot with your body language as well. But good remote team tools can give you something back.

edit: direct link to the app is https://sketchboard.me.

Searched Youtube for a demo. This was what I found:

https://www.youtube.com/watch?v=RB-Qjaa2vjQ

"Unlike the web, we're centralized so we control how much value we capture, much like twitter"

I shuddered.

Truth is I don't really like being in the seat of pair-programming anyway. I like to be free to make incredibly stupid mistakes while I feel my way to an answer and someone shoulder-surfing me inhibits my thought process as I wonder what they'll think of it rather than just the "it" itself.

It's okay as the shoulder-surfer though, especially when training someone.