The 12 Most Important Interview Questions to Ask Remote Workers


Asking the right questions during an interview is one of the most important steps in selecting the right candidate. When the hiring process is virtual, assessing a candidate’s hard and soft skills can be especially challenging. If your organization made the decision to hire remote workers and you’re unsure where to start, look no further! We’ve compiled a list of the most important interview questions you should be asking every candidate. 

Make sure you are hiring the right candidate by asking these 12 important interview questions before sending over an offer letter for a remote work position.

Questions About Remote Experience

1. Have you worked remotely before? 

You’d ask a candidate about their relevant experience for the position at hand, right? You need to do the same with remote work experience. Have they done it before? Do they have a clear understanding of the difference between reality and expectation? 

Knowing how they’ve worked remotely in the past (or what they envision that will look like) will prove whether or not they’re prepared for a remote position. Listen for insights into the way they organize and manage their time, how they communicate and whether or not they have the technical skills necessary to be successful. 

where do you plan on working

2. Where do you plan on working? 

If you work from home, you know how important it is to have a dedicated work space. You’ll want to check to make sure they have all the basic requirements: internet connection, quiet area for calls, etc. Asking this question will not only give you a sense of what they need to be successful, but also whether or not they’ve thought through the details of remote work. 

I’m certainly not saying you need to be tied to your desk at home either. The whole point of remote working is to have more flexibility. If your candidate is planning on working while traveling, just make sure that they have the tools and connection in place to do so effectively. 

3. What’s your biggest challenge when it comes to remote work and how will you overcome it? 

The answer to this question will reveal three things. First, whether or not the candidate has a practical understanding of the reality of remote work. Second, whether or not they are aware of their shortcomings. And third, whether or not they will preemptively look for ways to solve problems. 

Everyone struggles with some aspect of remote work. Even if you’re interviewing the most tech savvy youngster, they may struggle with isolation or lack the assertiveness to interject in a virtual meeting setting. It’s not only beneficial to know their weak spots, but also how they’ll plan around them. 

4. Why do you want to work from home? 

Everyone’s got an agenda. Understanding the motivations behind a candidate’s desire to work remotely can tell you a lot about the kind of employee they’ll be. Are they taking care of children or aging relatives? Living in a location that limits career opportunities? Just want to travel the world while collecting a steady paycheck? 

What you need to listen for is whether their motivations stem from personal or professional advantages. I’m not saying that people looking for personal gain won’t be hard workers, but you’re more likely to benefit from the hustle of a career-oriented individual. On a similar note, give bonus points to the people who not only mention how it makes their life better, but also how it makes them a better employee.

Questions About Virtual Communication

5. What digital communication tools are you comfortable with? 

Let’s be frank. Onboarding is an exhausting process for all involved. But having to teach someone how to use basic digital communication tools is an unnecessary headache. If you need to see proof of basic math skills before you bring on a finance specialist, you’ll definitely want to make sure a remote worker has the basics of digital communication down. 

If they have no experience with (or are easily frustrated by) digital communication tools, you may run into inefficiencies down the line. You need to know that they’ll be comfortable with basic troubleshooting. Remote employees can’t wait for tech support for hours every other day. How comfortable are they with the tools you use?

6. What’s your preferred method of communication?

Believe it or not, this question can give you a lot of insight into your candidate’s communication habits. Do they prefer the nonverbal cues in video meetings? The ease and speed of chatting? The familiarity of email? The real-time nature of a good old phone call? 

You’re not only trying to get a sense for how this person will communicate on a daily basis, but how well their style meshes with that of the team you already have in place. If you have regular standup video meetings, but the candidate hates showing face, how will that impact the culture of your team? 

7. How have you handled digital miscommunications in the past? 

Digital miscommunications are inevitable. They happen in every company, on every team. Whether it’s a misinterpreted emoji or a missed message, it’s going to happen. And if it’s not taken care of quickly, it can erode trust and sour the energy of a solid team. 

remote workers

You need to know that this candidate not only has the emotional IQ to address these issues, but is also aware of any quirks they might have that may lead to miscommunication. Are they typically jolly when on the phone or face-to-face but come across as short and dismissive in messages? Have they worked to overcome this? Inviting a toxic communicator onto the team is a mistake you don’t want to make. 

8. Have you worked with a distributed team before? 

Working on a distributed team is very different from working in an office setting. You’re going to want to make sure that this candidate not only understands the difference, but knows how to work with people in a remote or hybrid environment. 

Camaraderie is harder to come by when all interactions are virtual. Collaboration looks a bit different. Differences in schedules and time zones can mean waiting longer for responses. How will this candidate cope with these differences? How will they remain efficient and productive on this team? 

Questions About Remote Productivity

9. What does collaboration look like when you’re working remotely? 

Like I mentioned before, collaboration can look a lot different when your team is virtual. You can’t rely on whiteboards and conference rooms to spark creative debates, brainstorms and strategy sessions. So how do you initiate and maintain collaborative efforts when working remotely? 

what does collab look like

You’re looking not just for answers about what tools they use, but also how they go about interacting with others. It’s not enough to use a virtual whiteboard or convene a video meeting. How do they cultivate ideological safety and encourage participation through a screen? How does their answer fit how your team collaborates today? 

10. How do you make sure a project is successful when working remotely? 

This question tackles a number of subjects: collaboration, project management, organization, time management, communication… You need to find out how the candidate approaches a new project and how they will work with others to make sure it’s a success. 

Do they ask a ton of questions up front? Communicate with different contributors and stakeholders throughout the project? Take the lead? Follow directions to a T? You want someone who’s not only goal oriented but flexible in their approach. How will they handle unexpected challenges or a change in plans? 

11. How do you stay motivated and productive during the day? 

Working at home can get lonely. Not having the opportunity to gather around the watercooler or have a casual chat with a coworker can make your day feel endless and mundane. So how does this candidate schedule their day, keep up the energy and stay on task? 

Whether the position is hybrid or fully remote, you don’t want someone who waits to take direction. So prioritize the candidates who are willing to network with other departments, tackle some of the tasks in the backlog and keep themselves motivated. You don’t have time to babysit. 

12. How do you manage the boundary between work and home? 

You’ve likely experienced burnout in the last two years, or watched coworkers suffering from it. It’s devastating not only to the individual, but also to the company at large. If you want to protect your remote employees from burnout, you need to make sure they understand and maintain the boundary between work and home. 

Having an isolated workspace in the home and blocking out time for breaks isn’t required, but it definitely helps. Tell potential employees that it’s okay to take breaks during the day. Use your focus time wisely, but don’t be afraid to take the dog for a walk around the block, knock out a chore or make some lunch. 

Making the Right Remote Hire

Adding remote workers to your team is a great way to expand your talent pool beyond your city limits. You just need to make sure you’re hiring the right remote worker for your team. Hiring the wrong person can be a huge waste of time, energy and resources. Before you send over that offer letter, make sure you’ve asked these 12 questions and are satisfied with the answers. 

Katie Dudlets

Katie Dudlets

Katie Dudlets serves as TelNet’s Marketing Manager and Chief Storyteller. A whiteboard enthusiast and compulsive book collector, she can usually be found expounding on the advantages of corporate storytelling. When not at her desk, you’ll probably find her admiring the artistry of a well-crafted taco, petting a dog or zipping around Lake St. Clair on her jet ski.

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