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Are You Asking the Right Questions to Prospective Remote Employees?

During the COVID-19 pandemic, many companies sent employees home to work out of necessity. While the transition may have been challenging, this arrangement ended up being just fine for some teams and, in fact, many workers now prefer it. They appreciate benefits like having control over their environment, spending time with family members and pets, and avoiding long commutes.

Companies get benefits too, including reduced spending on office space and related expenses, and happier employees. Because it’s a win-win situation, some businesses are extending work from home (WFH) arrangements beyond the pandemic. However, those that rushed to get WFH plans in place in early 2020 may still be working out some of the challenges, including how to interview prospective employees for WFH positions.

Working from home isn’t for everyone and you need to know whether new employees will be well suited to this arrangement. That’s why it’s important to know what questions to ask during interviews. 

Fortunately, here at Workling, we’ve been working remotely since day one, so we have the know-how to help you. Read on to learn how to assess job candidates’ preferences, experience, and aptitude — including work environment, team, challenges, career development, and working independently — as well as specific questions to consider.  

Work Environment

One of the biggest changes from working in an office to working from home is the environment. At an office, all tools and supplies are provided by the employer and employees have little to worry about in terms of furniture, technology, and office supplies. When working from home, they at least need a space to put these things, even if the company still provides all the supplies. It’s important to ascertain whether employees are ready for this setup.   

Questions to consider: 

  • Do you have experience working from home?
  • If so, what tools and other items are necessary to perform your work? 
  • Do you have a dedicated space in your home for an office?
  • What are some of your cybersecurity practices? 
  • What challenges might you have in working remotely? 


Remote workers are still part of a team, even if the way the team works together looks different from traditional in-office arrangements. So, teamwork is essential for remote work jobs, including having shared goals and achievements, communicating effectively, and solving problems together. You can start to get a feel for the prospect’s presence and team spirit by conducting a video interview. 

Questions to consider: 

  • What are some best practices you’ve learned about working with a remote team?
  • What are some best practices you’ve learned about communicating with a remote team? 
  • What communication tools are you familiar with? 
  • Tell me about a time when you shared an achievement with a work team. 
  • Tell me about a time when you worked through a challenge with a work team. 


As with any life situation, working from home will present challenges. The issue here is how potential employees will deal with them. To get a feel of how an interviewee deals with challenges, you can ask about specific types of situations that are likely to come up in their working experience, including direction, communication, technology, work-life balance, and conflicts with other team members. 

Questions to consider: 

  • Generally speaking, how do you deal with challenges at work? 
  • What strategies do you use to keep your work and personal lives separate?
  • What do you do when you need more information to complete a project? 
  • What’s the first thing you do when confronted with a technology issue? 
  • Tell me about a time you successfully worked through a conflict with a colleague. 

The following video explains some of the primary challenges of remote work:

Career Development

Employees working outside of a traditional office environment might feel somewhat disconnected from their career path, especially because they don’t share spaces with colleagues nor do they network. They might wonder, “If I do a good job, what’s next for me?” These are valid concerns, and you’ll want to tell applicants how your company handles this issue. You’ll also want to get a sense of their expectations and concerns. 

Questions to consider: 

  • What is your preferred way to receive feedback on your work?
  • What growth opportunities are you looking for? 
  • Where do you see your career in 5 years? 
  • What people in our profession do you admire? 
  • Do you like having a detailed career plan? 

Working Independently

Experience working remotely isn’t necessarily a qualification for doing so now. Plenty of people who have never done it are capable of making the transition. Either way, though, you need to know whether job applicants have the core capabilities to do it successfully. They include good communication skills, ability to self-motivate, strong organizational competence, and the capability for self-evaluation.  

Questions to consider: 

  • What concerns do you have about working from home or about not working in a physical office space? 
  • How comfortable are you with asking questions when you don’t understand something?
  • How do you stay motivated? 
  • How do you stay organized? 
  • How do you know when a project is successful? 

Look for Red Flags

Of course, you want all interviewees to be successful, but the truth is some of them simply won’t be suited to a remote work arrangement. Therefore, look for the following red flags to weed out who may not be the right person for the job: 

  • Lack of remote work experience. Again, it’s not necessary to have remote work experience to do it successfully. But make sure the applicant has strong skills that will help them make a smooth transition. 
  • Lack of proper environment. Even a small space in the home can work as an office, but you want to make sure that space has everything the potential employee will need, including reliable internet access and the ability to minimize distractions.
  • Difficulty naming best practices. If an interviewee has trouble coming up with strategies for staying organized, staying motivated, communicating, and being successful without constant direction, they may not be cut out for a remote work position. 
  • Lack of familiarity with remote working tools. Of course, it may be necessary to train new employees on certain tools that your company uses regularly. It also helps if they’re already familiar with at least some of them. 
  • Difficulty overcoming challenges. Most interviewees won’t come out and tell you they’re not good at meeting challenges. But listen for subtle clues like asking for help right away. If that is their strategy, they may not be cut out for independent work. 
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