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How to Run a Workplace with Office and Remote Workers: An Interview with the CEO of RemoteYear

Sep 12, 2018 7 min readOpen
Photo of Hailley Griffis
Hailley Griffis

Head of Communications & Content @ Buffer

When we give remote work advice, we tend to give it from our own perspective, which is that of a fully, 100-percent remote team.

However, this way of working isn’t the norm — or even the standard. In our inaugural State of Remote Work study, we learned that most of the companies who support remote work are not fully remote; 65 percent of them have a combination of office-based employees and remote employees.

These “combo” companies — one of several types on the remote work scale — are often dealing with a unique set of challenging questions:

  • How can organizations be inclusive of remote employees?
  • What are the business benefits of some employees being remote?
  • How can businesses deal with having employees in various time zones?
  • What do you say to people who don’t believe employees can work while traveling and still be productive?
  • What advice do you have for an office-based business just getting started with remote work?
  • How do you build company culture with office-based and remote employees?

To help answer these questions, we turned to our friends over at RemoteYear, a company that allows remote workers to take their location-independent job and travel while working around the world for a year or four months, spending one month in each city. RemoteYear provides the transportation, accommodations, and workspaces with reliable WiFi.

This post is the result of RemoteYear’s CEO, Greg Caplan, graciously giving us an interview to chat about his best practices for remote work and thoughts on what the workplace of the future looks like.

RemoteYear CEO Greg Caplan
RemoteYear CEO Greg Caplan

1. How can organizations be inclusive of remote employees?

When we started chatting with the team at RemoteYear, it was clear that they were very familiar with this challenge: How do businesses who have both remote workers and people in the office make it work for everyone?

This split workforce marks a major shift for many businesses and industries that now need to account for and support “out-of-sight” employees for the first time.

Here’s what Greg had to say about that initial step of inviting remote work into the organization:

The difference between remote and non-remote employees is just communication. The way to be more inclusive of folks is [having] normal best practices like setting goals and having clear outputs, rather than relying on random interactions in an office. You need to be more intentional in the way that you communicate.

While discussing what this intentional communication looks like, Greg made sure to highlight goal setting.

It’s different for everybody, but you need goals. We structure ours based on annual goals that we break down into quarters and months and we have priorities each week that people move towards. Most of the touchpoint is during the weekly 1:1. I think everyone needs to have a 1:1 with all of their direct reports on a weekly basis.

One of the main things Greg stressed was that, with remote workers, it is important to measure people based on their outputs, not based on their face time.

Tweet this ☝️

One way we create structure for our team at Buffer is by using six-week product cycles to organize our goals and accountabilities. According to Greg, you can use any system that works for your team as long as you are being intentional about the system and working with your employees to set clear goals.

2. What are the business benefits of some employees being remote?

Greg made it clear (and we’d agree!) that there are plenty of business benefits when it comes to remote work. When it comes specifically to companies sending employees on RemoteYear experiences for four months or one year, he elaborated on four main benefits for businesses.

1. Talent traction

We’re starting to see lots of companies starting to use RemoteYear and other flexible options to acquire talent. There is talent that is getting more and more difficult to recruit and this is a great opportunity to do that.

Greg shared this example: when Fiverr started allowing employees to go on RemoteYear, the number of job applications they received grew by over 200 percent with twice the amount of qualified applications.

2. Talent retention

There are a lot of people who otherwise wouldn’t stay in the role they’re in because they might want to go travel or require more flexibility for their lifestyle, so [offering more] flexibility is a really great way to retain talent.

3. Employee engagement and recognition

For this one, Greg had some really interesting data to share:

It’s been shown that [companies] have + 48 ENPS for folks who have flexible options.

4. Learning and development

If you think about RemoteYear exposing people to a global experience, they build all kinds of skills like global perspective, which is increasingly important as more companies are globally minded with a global customer base.

3. How can businesses deal with having employees in various time zones?

The timezone challenge is one we work through at Buffer a lot; our marketing team alone works in seven different time zones.

Greg shared two main tips:

  1. Make communication asynchronous
  2. Build teams to accommodate for different time zones

Greg’s tailored approach involves really thinking through the needs of each team.

You have to think for each team specifically what’s going to make the most sense. If you need real-time communication, then you should build your teams to be more sensitive to timezones.

He explained that this doesn’t need to affect the talent pool benefit that remote work provides, and that teams can still hire globally. They just need to be mindful about when real-time communication is necessary and when they can communicate just as well asynchronously.

Like us at Buffer, Greg has interacted with companies that are intentional about spreading teammates out across various timezones. “There are some organizations have said that there are some benefits to having folks on the opposite end of the earth where they can focus on different customer needs.”

Photo by Helena Lopes

4. What do you say to people who don’t believe employees can work while traveling and still be productive?

This is a question we get a lot at Buffer and we completely agree with Greg’s answer:

It’s about having trust in your employees.

We’ve found that it’s possible to build this trust from the very beginning of a work relationship, though Greg mentioned that this might be easier with employees who have been around the company for some time. “It’s very difficult to start a new relationship with somebody and go to that level of trust,” he says. “Usually the way to get comfortable with that is to have a level of trust and understanding of the person by already having worked with them before they enter this kind of journey.”

Another way that Greg would answer this question would be to emphasize why offering remote work options should be essential for companies. “Organizations that aren’t able to successfully adopt those policies and the workplace culture that can interact with [remote workers] are going to lose out on the talent wars and they are going to get disrupted by their competitors,” Greg says.

When I asked him about the talent wars, Greg expanded his perspective: “it’s getting more and more challenging to fill roles at the quality standard that people have had historically if they don’t open themselves to different types of geographies than just within 20 miles of their headquarters.”

5. What advice do you have for an office-based business just getting started with remote work?

If you’re convinced that you want to get started offering remote work, here are some ways to get started.

The best thing to do is to start small. It’s hard to make a massive shift from day one. A lot of companies I talk to start with [offering] one day a week working from home. I think kicking people out of the office gets some comfort and familiarity with it and really forces the organization to build the processes they need to accommodate other folks.

His other idea for organizations getting started involves choosing one person to move the project ahead. “The other way to start small is to start with one person and have that person be a champion for best practices,” he says. “In order to do that well you really need to empower that person to give feedback and help the organization, rather than just be cut off from the culture.”

“It’s important that organizations don’t jump into remote work too fast,” Greg added, “but also that when they do take the first step, they are thoughtful about it and they learn throughout the whole process and then adapt and build.”

6. How do you build company culture with office-based and remote employees?

This is one of the most common questions about supporting remote employees, to this Greg says, “I think that’s it’s really difficult to build culture in a 9–5 when you’re sitting one desk away from someone, you generally don’t interact with them at all in an office environment.”

So what’s the solution? According to Greg, “you do build culture and relationships and trust outside of the office, so dinners, lunches, events.”

He was kind enough to mention Buffer retreats as an example here. Once a year we bring the whole team together for one big company retreat, and we’ve also started annual mini-retreats where individual teams at Buffer can gather for a week at another point in the year.

Greg says the reason that this type of offsite works so well to create culture is that “[they] build better relationships and interactions and trust with the other folks because you’re having a travel experience and you’re able to connect with folks in authentic ways.”

He added that, “I don’t think there’s a lot of culture or co-located value that comes from being in an office, but there is a huge amount of cost, and people only think of the value loss and not the cost-benefit gain.”

Over to you

A big thank you again to Greg for making the time to do this interview! We hope you enjoyed it. Now we’d love to hear from you.

  • Do you work at a company with an office that also offers remote work?
  • What works well with helping office-based and remote employees stay connected?
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