How to Successfully Hire and Manage a Remote Workforce

Hiring remote workers isn’t just trendy. It’s actually a strategic move that many forward-thinking businesses are taking advantage of today. But not everyone is cut out to work remotely, and there are several ways you can determine if a candidate is a good fit for this arrangement during the interview process. 

Earlier this week, we asked two Boston-based remote employees - Dania Lieberthal, a sales manager for Test Double, and Devin Bramhall, Director of Content for Help Scout - to share their perspectives on what kinds of companies fit the remote work business model. You can read that post here. For companies considering going all-in on remote work, Lieberthal and Bramhall had some additional insights from the frontlines.

Here’s what they had to say.

Be Deliberate

First of all, if hiring a remote workforce is going to be part of your company’s success strategy, then it needs to be baked into the DNA of the business. “It’s not magic that remote works for us. It’s on purpose,” Bramhall remarks. 

“Help Scout has been a remote-first team since day one,” explains Bramhall. “It’s on our website, we write about it on our blog, and we explain our remote process on our hiring pages so that it’s clear to everyone how we work.”

“Every tool and process we use is deliberate,” she concludes. Because everything is well thought-out and intentional, Bramhall finds her team to be incredibly well-connected and close-knit.  

Hire Smart

Of course, remote work isn’t for everyone. So how do you find the right talent — the people who will thrive in a remote environment and who you can trust to get their work done without direct supervision? “We focus on hiring really self-motivated people. That in itself weeds out people who aren’t a fit for a remote culture,” says Lieberthal, who is deeply ingrained in Test Double’s hiring process. 

“Our interview process is rigorous so that we can verify who will do well in this type of environment. It’s not for everyone,” Lieberthal continues. “We have a soft skills interview where we ask candidates if a remote environment is something they’d be comfortable with, if they have experience working solo and if they have a home office,” Lieberthal says. “Depending on their answers, you can pretty quickly determine if they’d be the right fit or not.” 

Hiring team players is just as important for a remote team as it is for a traditional workforce. 

“Culture is really important to us. We need to be sure that a candidate is willing and able to contribute to the company culture, too,” explains Lieberthal.

For a remote team, the watercooler is replaced by Slack, monthly team outings are replaced by yearly retreats and meetings are held virtually by video. It’s important that a candidate is willing to contribute often and eagerly to these team-building initiatives. 

Develop an Asynchronous Work Culture

Remote teams need to support a wide array of time zones and schedules, so there needs to be a deliberate process for communication and information-sharing. This way, regardless of whether someone is workingin the U.S. or Australia, they have access to the same information and can be productive according to their own schedule.   

Help Scout has employees spread across the globe, from Australia to Amsterdam and from the U.S. to the U.K., and they recognize that employees can’t (and don’t need to be) online at the same time to get their work done. But they do need to have a strong connection with the team nonetheless.

How do you achieve this? Help Scout ensures that there are at least a few hours during the day that everyone overlaps so that people can have team meetings during the workday. 

The rest of the time, the team relies on tools to collaborate. “We use Slack for ongoing communication, Trello for project management and Dropbox for storing files,” Bramhall says. “Between our communication apps and collaboration processes, we’re able to stay in sync no matter what time zone we’re in.”

Invest in Your Employees

Job satisfaction is the engine of an effective remote team, and to foster that, companies need to invest in their employees. “Our company invests a lot in its employees,” says Lieberthal. “They're extremely dedicated to making sure we’re healthy and happy.” At Test Double, co-founders have a 1:1 with each team member on a monthly basis. The first 1:1 is technical, where each employee talks through problems they’ve encountered and learns new techniques and tools. The other 1:1 is for talking about personal goals and how the company can help employees accomplish them.

In fact, Test Double encourages employees to spend 20 percent of their time each week on personal growth, whether that’s spending time on a hobby or side project. This sends a powerful message that the company cares about people — not just as employees, but as human beings.

Invest in Facetime

Both Test Double and Help Scout also bring their teams together for yearly in-person meetings. “We talk through company culture, problems, gather feedback on what we can be doing better, and more,” says Lieberthal. The in-person time is invaluable for bonding, and helps set up the culture for success throughout the rest of the year.

Though arranging this in-person time can be logistically challenging and pricey, these retreats are well worth it for the effect they can have on remote employees. “I know our yearly company-wide retreat isn’t inexpensive, but we all get so excited to be together, talk about ideas and give feedback,” explains Bramhall. 

These “in real life” get-togethers can also help the company troubleshoot any issues that spring up. For example, Lieberthal says, “Some of our team members expressed at our latest retreat that they were starting to feel disconnected, so we decided to implement ‘coffee with co-workers’ where each week we’re paired with another co-worker for a 15-minute video call to talk about anything but work. We’ve been doing it for about a month now and people are really happy with it.”

Will Remote Teams Become the New Normal?

As companies like Help Scout and Test Double go all-in on remote work,  does that mean other businesses can or should follow suit?

“I hear a lot of people talking about it now, but tentatively and with much trepidation,” reports Bramhall. “I think if you’ve never done it before, it’s hard to imagine.”

In some cases, it may just be a matter of embracing the concept. “There’s also a big difference between remote work being an option and it being a part of the culture,” explains Bramhall. “There’s a guilt factor about working from home if it’s only offered as an option, so it often doesn’t work. But if you create an all-remote culture and do it right, it can be really effective.”

For companies looking to embrace a remote-first culture, Lieberthal and Bramhall unanimously agreed that it should start at the leadership level. The level of trust required for remote teams to succeed needs to come from the top and trickle down. “Leadership should then work to develop clear processes and implement tools to set the team up for success,” says Bramhall. “It has to be deliberate to work.”

We’re excited to see how Boston companies and employees continue to embrace remote work. Done right, remote work can help companies attract and retain top talent across the globe. Taking the steps to create a remote culture does take time and work, but as we saw when we took a peek under the hood at Test Double and Help Scout, the results are well worth the effort.