communicate communicate communicate
I've worked in several jobs with remote teams (as the team and managing the team) and the difference between the ones that worked like clockwork and the ones that didn't almost inevitably came down to communication.
The amount of time and energy sorting out problems because of a lack of communication will absolutely dwarf the amount of time you should have been communicating.
- Have at least 1 weekly roundup, guaranteed, no exceptions. Even if it's just for everybody to get together and say they have nothing to report, that is even in and of itself a communication. Some places did daily end of the days, some did Mon & Friday mornings, it doesn't matter. Do it.
- Use more efficient communication proxies when possible: trello, jira, salesforce, whatever. Enforce it with an iron fist. Don't let people get away with not using the tools, they're easy to use and if you get in the habit, saves hours upon hours of time. I love love love Trello for this.
- Have constant ad hoc communications. IM, phone, email. Schedule times so you don't interrupt somebody's work day. Missing a scheduled time should be a shocking breach of protocol.
- Please try not to use speakerphone or conference room speaker phone, it makes the meeting unpleasant on the other end and much harder to undertand.
- Google docs, really great for drafting up things and early collaboration. Switch to Office for the final work.
- if you can afford it, have as many face-to-face meetings as possible, be it once a week, or once a quarter, or once a year. Try and make the effort. I've found that learning people in-person helps smooth over digital communications.
- document document document - everything. Have a centralized and constantly organized document repository. People leave, sometimes without doing a good handoff. Not having good documentation will kill a company for months or years.
I agree with most everything else here: especially "5. Hire people who are ok without a social workplace."
Amazingly, most people don't actually realize what it means to work alone every day, all day. I've had a couple people go a bit loony and flake out after a few months on their own. The environment was discussed, and they felt confident about it, but simply couldn't handle the reality of it. If this is a requirement, prepare for issues no matter what. Try and hire people with a track record for this kind of work.
One guy ended up hitting bottle pretty hard (bars can be chatty places), his wife filed for divorce, and he simply stopped showing up to work. Working remotely it took a couple of weeks of no shows on the weekly all together to figure it out. He ended up quitting and moving to the desert to sort his life out. Working alone simply shattered him.
And finally,
"4. Hire people who can write"
You wouldn't believe how many emails I've received from certain remote workers that are utterly indecipherable. You think most native speakers of a language with some college in them can write an intelligible email. It turns out many can't. And you waste lots of time clarifying, making phone calls, etc. And the worst case is you go off on the wrong direction.