Ask these 4 questions before hiring a remote worker

This manager has worked with remote team for 10 years, and has learned that in order for remote teams to be successful–you need to set them up to do so.

Ask these 4 questions before hiring a remote worker
[Photo: Yusuf Evli/Unsplash]

With the U.S. labor force hovering near full employment, companies across the country are facing increasingly fierce competition for top talent. For skilled workers, it’s a job-seeker’s market. This means that employers need to do more than just post job listings, and think about putting incentives in place to attract the best talent.


One way that employers are doing this is by opening their pool to remote candidates. To many job-seekers, it’s a perk, and it also allows a company to broaden their talent search beyond their immediate geography.

I’ve spent the last 10 years working with remote teams, and for eight of those years, that involved managing people across many different time zones. Sure, remote systems don’t work for every person or team, but in my experience, companies have a lot to gain by implementing a remote work policy. In addition to attracting more candidates, you can also use time zones to your advantage to move projects forward around the clock and offer better work/life balance to your employees.

But to reap the benefits, companies need to be prepared to adjust their systems and practices and set up remote workers for success. In my experience, asking these four questions before you hire a remote employee can go a long way.

1) Is this position well-suited to remote work?

Even in the age of Slack and Google documents–some roles just don’t work well remotely. For example, if you’re hiring an office manager or administrator, they should probably be present in the office. You need to ask yourself this before you even start considering candidates–because if it turns out that being remote is a hindrance to their role, you’ll probably face expensive and time-consuming problems down the line.

Related: How these remote workers convince their bosses and clients they can work anywhere 


2)  Can this candidate be effective in a remote setting?

Not everyone can be a remote worker. For starters, someone who isn’t a proactive communicator or needs constant social interaction to thrive can really struggle in this kind of setup. When you’re evaluating candidates, you need to understand if their work habits fit the needs of a remote role. This is a little tricky, but having a consistent interview plan can make all the difference, mainly when hiring for a technical remote position.

At DigitalOcean–where I currently work–we have a specific process for our remote employees, who make up 60% of our company. They go through a recruiter screening first, followed by a more in-depth conversation with a manager and a technical interview. We make sure to conduct most, if not all, of the interview process remotely, because that gives us a chance to assess how a remote hire might work on a day-to-day basis.

We always make sure to ask our remote employees the following questions: 1) “Have you worked remotely in the past?” and 2) “How do you feel about working remotely?” This forces the candidates to think about how they would work when they’re not physically in the office–and you can gauge whether their working style suits that arrangement.

Related: Four reasons to hire digital nomads (like me) 

3) How can I hold my remote team (and myself) accountable?

The work doesn’t stop once you’ve hired someone. Sound management principles for remote employees are mostly the same for those who work in the office, but when you work across multiple time zones, you need to take extra care to keep projects on track.


At DigitalOcean, we have a daily standup meeting via video-conferencing where we share updates on what we’re working on that day. This practice takes time and commitment, but I have found that goes a long way in keeping everyone connected and informed. In lieu of office chitchats, these meetings are an excellent way for remote team members to have virtual “watercooler conversations” with each other. This helps improve group cohesion.

As a manager, I tend to share what’s happening at the leadership level during our daily standup, and as much as I can, I communicate how our team’s work ties back to larger strategic goals for the company.

You don’t necessarily have to use this method–but it’s vital that you have a single, shared system for tracking progress on team deliverables. That way, everyone is clear on what they need to accomplish, and they can have something to refer to anytime they’re unsure of their priorities.

Related: Why employees say these companies have figured out flexible work 

4) How can I keep my remote team motivated?

It’s a challenge for any manager to keep their team motivated, and remote work adds another layer of complexity to the mix. Loneliness is a huge problem among remote workers and the lack of in-office face time might also lead to higher anxiety around job security.


In addition to keeping your team on track, it’s equally crucial to keep them connected so you can combat those potentially negative feelings. I try to schedule planned face-to-face time at least three times a year with my remote team, and I put extra effort into recognizing and (visibly) rewarding great work. After all, saying “good job” while I pass them in the hallway isn’t an option for me.

I’ve also had to be proactive with asking how my employees are feeling. It’s a little harder to notice when someone might be going through a difficult time–so as a remote manager, you have to go above and beyond to make sure that they’re happy at work.

There are a lot of benefits to hiring remote workers–but to see success, you have to be deliberate in designing the role and your work process. Start by asking yourself these four questions, and you’ll find it much easier to work through your next steps.

Alexis Bruemmer is an engineering manager at developer cloud provider DigitalOcean, where she leads a team of 11 engineers across three countries and five time zones.