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7 Questions to Ask When Hiring Remote Employees


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Bill Gates, founder of Microsoft, once said, “The competition to hire the best will increase in the years ahead. Companies that give extra flexibility to their employees will have the edge in this area.” His prediction was right—much of the future of work rests on employees who work from anywhere and everywhere, with unique work schedules that can look vastly different than today’s.

Flexible work can offer major advantages to organizations. A Gallup study found that organizations that offer job flexibility show 41% lower absenteeism, 40% fewer quality defects, and 21% higher profitability compared to those that don’t. At the same time, employees who enjoy flexible work schedules show significantly higher engagement, less stress, and higher productivity.

Remote work post-COVID-19

The massive work-from-home experiment brought on by COVID-19 proved that many organizations can depend on remote employees to keep business operations flowing. In fact, some say organizations that openly embraced remote work are much more likely to survive—and even thrive—through the pandemic. 

A recent Gartner survey on 317 CFOs revealed that 74% of companies plan to permanently shift to more remote work post-COVID-19. Nearly a quarter of those plan to move 20% of their on-site employees to permanent remote positions. 

As COVID-19 restrictions loosen and organizations plan their recovery strategies, hiring remote employees might be on the table. Organizations are prioritizing employee safety, and traditional cramped office spaces won’t make the safest places to work. Instead, many employers plan to continue working remotely—at least until the end of 2020. That means hiring both short-term and long-term remote employees.

Remote employees pose a new set of hiring challenges that differ from traditional, in-office roles. For example, if remote employees don’t manage their time effectively, distributed teams can easily fall into productivity black holes. Vetting candidates for great remote work attributes will be vital to developing teams that drive positive business outcomes.

Here are several questions to ask candidates to determine if they match your business needs:

1. What’s your remote work experience?

Many candidates are attracted to the idea of working remotely but don’t fully grasp the expectations and requirements of it. For example, candidates who’ve only worked on-site might not communicate as effectively or frequently online—an essential practice for remote work.

If they’ve worked remotely before (even partially or as a temporary arrangement, such as due to COVID-19), ask them about the challenges they faced. This helps determine that the candidate understands the hurdles of remote work and whether they overcame them.

2. What is your home office like?

Candidates committed to remote work have intricate home office setups that support their flexible work life. These could range from simple setups like a dedicated work desk to an entirely separate room designed for optimal remote work. On the other hand, candidates who haven’t prepared for remote work might lounge around on their couches and beds, which doesn’t always foster productivity.

3. What productivity apps are you familiar with?

Remote teams survive on technology that allows them to communicate and collaborate, so experience using productivity apps will be a critical trait of employees who successfully work remotely.

Look for candidates with extensive experience using cloud-based communications products, such as team messaging and video conferencing. Workers who consistently use remote communications tools are much more likely to collaborate with their teams and avoid working in silos. Ideally, your organization provides employees with a unified communications solution, allowing new remote employees to easily integrate into every conversation and hit the ground running.

Also, look out for candidates who regularly use cloud-based project management apps like Asana or Airtable. These apps allow entire teams to manage and track the progression of tasks wherever employees work. Because managers can’t simply walk to their desks, remote employees should provide more visibility to their work by consistently updating these apps.

4. How do you stay focused?

Offices aren’t free from distractions, but home environments can be full of them. Remote workers might easily focus on tasks until their city starts drilling through the concrete outside or their children come home from school and expect entertainment.

Experienced remote workers understand how to tune out distractions. Many use noise-canceling headphones to drown out noises. Others dress how they normally would in the office to maintain their professional headspace. If a candidate has a specific strategy for staying focused, they’re likely to make a better remote employee.

5. What kind of hours do you work?

Chances are your team has specific hours where everyone is available and reachable. Remote workers, however, might have different preferences in their work schedules. Life obligations might compel certain candidates to start work in the late afternoon. Although they might have the skills to excel at work, their work schedules have to match with your team and the organization at large.

6. How do you switch off from remote work?

Remote employees are more prone to burnout than their in-office counterparts. According to a study by Airtasker, remote employees work 1.4 more days per month on average than office employees, and a study by Buffer found they take less vacation, too. With poor self-management, remote employees can experience fatigue, isolation, and lower productivity.

Great remote workers know how to “turn off” work mode by properly scheduling breaks and using do-not-disturb indicators on their team messaging apps. They might also have healthy life habits such as regular exercise to cope with the expectations of a fast-paced organization.

7. Why do you want to work remotely?

This question tells you everything about a remote work candidate’s motivations. While 90% of employees want flexible work arrangements, some might want them for the wrong reasons. For example, candidates who simply want to escape from nagging bosses likely won’t consider the larger organization’s interests. Conversely, candidates who explain that working from home boosts their productivity and allows them to drive better business results can see the bigger picture.

Set remote employees up for success from the beginning with communications technology

The remote talent you hire will determine the success of your teams, so it’s important to ask the right questions from the start. Interest in remote work continues to grow, and organizations are increasingly embracing it—especially post-COVID-19. In order for your organization to stay competitive, make sure your future remote workforce is prepared to meet your business needs and drive positive outcomes.

Supporting remote employee productivity starts with having the right communications technology. Remote employees and distributed teams need to collaborate effectively regardless of their location. Unified communications solutions like the RingCentral app combine team messaging, video conferencing, and phone into a single platform where employees can communicate from anywhere and on any device, allowing them to focus less on technology and more on collaboration.

Originally published May 30, 2020, updated Jan 18, 2023

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