This is a topic I've spent a LOT of time wondering about, as well as a fair amount of time failing at managing. Very idealistic view of the subject from a professional Millennial.

So what's your opinion? Why does remote work succeed in some companies?

A completely distributed company born out of the open-source movement, Automattic doesn’t make anyone come to the office — and most of its employees choose not to. They’re given state-of-the-art technology, $2,000 to build a home office, and a large travel budget so they can meet up with other team members twice a year in beautiful, exciting places such as La Paz, Mexico, and Amsterdam. Ultimately, these perks help the company source the best talent, which is often found outside large technology hubs like Silicon Valley and New York.

Elsewhere, though, it’s been a different story. Marissa Mayer famously declared the end of remote work at Yahoo! about two years ago, citing the need to improve the “speed and quality” and benefit from the “decisions and insights [that] come from hallway and cafeteria discussions.” In the wake of her controversial decision, several high-profile companies — including Best Buy and Reddit — followed suit.

So what’s the problem? The answer is simple: Many companies focus too much on technology and not enough on process. This is akin to trying to fix a sports team’s performance by buying better equipment. These adjustments alone might result in minor improvements, but real change requires a return to fundamentals.

Successful remote work is based on three core principles: communication, coordination, and culture. Broadly speaking, communication is the ability to exchange information, coordination is the ability to work toward a common goal, and culture is a shared set of customs that foster trust and engagement. In order for remote work to be successful, companies (and teams within them) must create clear processes that support each of these principles.

...

GitHub, which makes a platform for collaborating on software development, brings its entire team together once a year for this purpose. It also requires new hires to spend their first week in its San Francisco headquarters so they develop an understanding of the company’s culture. GitHub also rallies around its online platform with rituals that feed the culture and provide recognition for employees. One example is its #toasts forum, which functions as a virtual water cooler. Employees post major accomplishments to the forum, and colleagues from around the world post selfies toasting them — though they’re usually not drinking water. In the end, these photographs are made into a short video and uploaded to a shared repository. (To see this in action, check out this talk by a GitHub employee, at 15:25.) For remote workers located around the world, this type of quirky activity provides a connection to colleagues and to the company’s unique culture.

I actually did a lot of reviewing of the academic research literature remote workers and this article is surprisingly on target.

Joyce, bottom line is that it's much more difficult than it seems.

The biggest secret to success that I have found is to recognize that you have to communicate the same message multiple times. Problems happen when you tell someone something and therefore assume they got it. I don't really understand why but a remote employee can hear what you are saying, understand it and then somehow fail to internalize or act on it. Whereas if the same information was given face to face in an office setting it would have been heard, registered, and acted upon. 

The initial tendency is to blame the employee. "I told you that already!" but for whatever reason this is very par for the course for even the best remote employees.

At first it feels weird saying the same message multiple times but eventually it becomes the norm. Repeat it a few times verbally over the phone, post it again on a company forum, discuss further on secure IM.

Is the problem phones? Does it get easier with emails or Slack?

No, the research concludes it doesn't matter the medium, it's the repetition that's important. I think it has something to do with the fact that in an office environment things are being continually reinforced without you even realizing it. (Though I don't know what Slack is so I can't speak directly to that.)

Slack is a productivity app that lets teams communicate efficiently: http://slackhq.com

I think I hear what you're saying. The more hours a team works together -- regardless of location -- the more effective the team is working together. The problem remote teams have is not enough time together.

Say that again? :)

Well played, sir.

Yes, except that I'd change one word. The more hours a team IS together -- regardless of location -- the more effective the team is working together. They don't have to be working per se. Things get reinforced just being together.

And the surprising thing is that it's not just that the time together improves how well they work together, it also improves how well they work individually. And that is the crux of the remote worker management challenge.

It's just hard to tell when someone is remote how much they're actually absorbing from their team.

That's right. And even if they say they've "got it" they don't always. Luckily the other advantages of a remote workforce make it worth the effort to figure it out. Pros and cons to everything, right?

Right! The older I get the more I accept the fact that everything is about tradeoffs.