When Bryant Burnheimer approached his bosses at Higher Logic—a company that specializes in cloud-based community platforms—about working remotely for an entire year in different cities around the globe, it took some time to get their heads around the idea. Burnheimer, an implementation project manager at Higher Logic, applied and was accepted to Remote Year, a program that allows a group of professionals to travel the world for a year while still holding down their jobs, albeit at a distance.

While some of the company's executive leadership had initial concerns, ultimately they saw a major benefit. "[We] realized Bryant's year abroad would present great opportunities to share stories that convey Higher Logic's culture," says Heather McNair, vice president of engagement strategy. "Higher Logic has always put itself out there as being very progressive and being very open to doing things differently. … We thought it would be an interesting experiment to see if we could make it work."

Here are some lessons that other association managers might consider when supervising remote staff:

1. Create a plan that benefits the company. After applying, interviewing, and getting admitted to the Remote Year program, Burnheimer still needed to get Higher Logic's blessing. Burnheimer says he wasn't too worried about getting the go-ahead, especially since he says the experience matched the company's mantra of building online communities, growing online engagement, and connecting people around the world.

He created a detailed pitch and work plan for what he felt the company could accomplish through his participation. This included face-to-face meetings with international clients, spreading the word about Higher Logic abroad, and developing his own communications skills.

2. Make sure remote work is the right fit. Having started with Higher Logic back when it was a startup, Burnheimer built a lot of trust with the company's executive team. And, as an implementation project manager, more than 95 percent of his work is done by phone, email, or Skype, McNair says, so the job requirements can really be accomplished anywhere.

We realized Bryant's year abroad would present great opportunities to share stories that convey Higher Logic's culture.—Heather McNair, vice president of engagement strategy

Still, Burnheimer says, "you have to be confident in your work, and you have to be organized. You have to be ready to have your own schedule. Nobody is checking to see if you're coming in every day, so you have to do that on your own." Not everyone fits that bill, so it's important for managers to know whether their employees are cut out for the autonomy, self-motivation, and organization that remote work requires.

3. Communicate with the rest of the staff. Although some of Higher Logic's staff works from home one or two days a week—and a small minority of others work completely remotely, after moving out of the area—the company's leadership wanted to make sure that its intent with Burnheimer was clear. Just because Higher Logic was doing this with one employee didn't mean the rest of the staff had carte blanche to work completely remotely. "At an executive level, we made it very clear that this was an experiment and that we're trying this with one employee," McNair says.

4. Overlap your hours. So far, Burnheimer has traveled to Spain, Portugal, Morocco, Serbia, Vietnam, and Cambodia. In the Asian countries, where the time difference is as much as 12 hours, he worked what he calls a hybrid East Coast schedule, which meant starting work at noon, taking a break for dinner, then hopping back online until midnight or so, to ensure that he was overlapping a few hours with his colleagues on Eastern Time.

5. Take into account hidden costs. Higher Logic also wanted Burnheimer to attend its annual meeting in Arlington, Virginia, but that meant flying from Vietnam. "It was very much worth it, but the cost was higher," McNair says. "It's those things that you have to take into account when you're approving something like this. Who's going to foot the bill for something like that? Is it going to be the employee or the company?"

6. Keep in touch with meetings. Skype has been an invaluable tool. Bettina Fowler, director of client operations at Higher Logic, and Burnheimer have a weekly Skype meeting, where they catch up about workload—whether he needs more or has too much, and if he's able to take on any special projects. He also participates in weekly team meetings to keep connected with the rest of his colleagues.

More than halfway through his remote year, Burnheimer says the experience has been challenging yet rewarding. Higher Logic's leaders say they miss having him around the office. He's looking forward to being reunited with colleagues too, but with five months to go in the program, maybe not quite yet. After all, South America is up next on the itinerary.