16 Interview Questions to Ask Remote Workers

16 Interview Questions to Ask Remote Workers

Many companies that adopted a remote workforce model due to the COVID-19 pandemic decided to switch to it long term, requiring HR professionals and hiring managers to adjust their recruitment efforts to address the different skills required by a virtual workforce.

Interviews are excellent opportunities to assess potential remote hires and their ability to flourish outside of a typical office environment. The following 16 interview questions will provide key insights about how a worker will perform as part of your remote team.

1. How long have you been working remotely?

Experience matters when you’re hiring someone for a job, and it extends to an interviewee’s experience as a remote worker when searching for remote talent. Someone adapted to working in a home office understands what it takes to succeed and be reliable and happy in a virtual work environment. Start by asking a candidate how long they’ve been working remotely, then transition to more specific questions to allow them to elaborate.

Follow-up questions

  • Have you worked as part of a distributed team before?
  • How do you remain focused on your tasks?
  • How do you stay organized and manage your time?
  • Where do you prefer to work?

2. Do you have a proven track record of success with remote work?

It’s helpful to establish whether the interviewee has delivered results as a remote worker at the outset of your interview, and it sets the tone for the rest of the conversation. Someone with extensive remote experience will have the personal and practical resources to succeed within a distributed team. Once they answer, you’ll know whether they’re speaking from experience or speculating about what remote work might be like.

This question is great for independent professionals as well as potential full-time employees. Most interviewees with a proven track record of success remotely working will have done so for a few years and will express enthusiasm for remote work. Seasoned remote workers who work well in a distributed team have thrived in a virtual office, are likely to have been promoted, have increased their pay over time, and have a portfolio of strong results. Ask candidates why they think they’ll thrive in remote work at your company and in the job they’re applying for, and then segue into additional questions such as those below.

Follow-up questions

  • Why have you been successful as a remote worker?
  • What aspects of remote work do you most enjoy?
  • What skills do you possess that have contributed to your success with remote working?

3. What will you find challenging about this remote work arrangement?

As millions of workers have discovered in light of COVID-19, remote work presents distinct opportunities, difficulties, and necessary adjustments. This question allows interviewees to demonstrate they have the self-awareness and foresight to anticipate challenges that may arise.

Importantly, this query also speaks to their interest in the role. If they’re considering this remote opportunity, they’ve probably wondered about potential obstacles. It’s also a key measure of their humility. In answering, the interviewee can admit where they may struggle, which is a key skill for successful professionals.

Thoughtful, specific responses to this question demonstrate an interviewee is being honest, insightful, and evaluating the opportunity seriously. In addition to identifying challenges, ask questions that invite them to present solutions they’ve developed to address and overcome past challenges.

Follow-up questions

  • How do you plan to handle these potential challenges? (if they don’t suggest solutions themselves)
  • How could our company support you in dealing with those potential challenges?
  • In your professional life, what are some examples of overcoming similar challenges?

4. What techniques will you use to stay motivated and focused while working remotely?

While organizations can take meaningful steps to support their remote employees, remote workers must develop their own strategies for staying productive and engaged. In fact, one of the key advantages of remote work is that talent is empowered to work in ways tailored to their needs and preferences.

This question allows you to assess whether a worker has developed techniques to support their own success (a sign of professional maturity) and whether those methods will match your team’s ways of working (a key practical concern). For example, remote workers may feel most productive when they work through the night and sleep until noon, but that might not fit with your practice of team meetings each morning.

Candidates worth pursuing will have developed a set of personal techniques that help them remain productive and engaged. It could include taking scheduled breaks, keeping fixed hours, choosing the right playlist, or regularly reviewing KPIs (key performance indicators). Keep in mind the point is to find a fit versus judging their habits. Additional questions will help you determine if their remote work habits align with your team’s way of doing things.

Follow-up questions

  • Members of our team have had a lot of success doing [a technique your team uses]. Does that sound like something you might find helpful?
  • How do you think you could use [a technique they mentioned] to handle [some aspect of the role that might prove challenging?

5. What remote communication and project management software and tools are you familiar with?

Anyone working remotely as part of a team or who interacts with clients and customers throughout the day must know how to use communication, productivity, and collaboration tools and be comfortable adopting new technology. This is paramount to success as a remote worker.

Most people who’ve worked remotely will have used several software applications and technologies. Beyond asking an interviewee which tools they’ve used, ask questions that reveal their depth of use and knowledge and how they rate their technical skills.

Follow-up questions

  • How often throughout the day did you use these tools?
  • Did you feel you were proficient in using them? Why?
  • Were there any tools you wish a company you worked for used and why?
  • Are you familiar with any of the tools our company uses?

6. Can you describe an instance where you proposed a new idea and saw it through to completion?

Self-starters are valuable in virtually any working arrangement, but they can be especially important within distributed teams. This question is designed to gauge an interviewee’s autonomy and capacity to execute their own plans.

Remote workers often collaborate across differing schedules and time zones and rely on asynchronous instruction. In moments when they can’t get immediate feedback, will they flounder? Can they contribute constructively on their own?

Whether it pertained to a new initiative or improved upon an existing one, get a clear example of an idea they conceived and effectively executed by asking this question. If the role a job candidate is interviewing for doesn’t require much independent creativity, ask if they can explain a problem they’ve encountered and how they proactively developed a solution. If the role requires creativity and independent thinking, follow on with questions that help them delve into the details of experience and skills.

Follow-up questions

  • How did you communicate your idea to others and enlist their support?
  • In this role, if you came up with a different way of doing things, how would you communicate your suggestion to our team?

7. Describe a time when you didn’t succeed. What did you learn from that experience?

Remote work is rarely entirely smooth sailing. There are often technical or interpersonal kinks to work out when joining a distributed team. Plus, setbacks happen in any team, whether you’re in the same office or on separate continents. This question allows you to assess whether the interviewee can roll with the punches and work toward improvement.

Their answer may also indicate their approach to constructive accountability. If the interviewee is quick to blame others rather than acknowledging their own shortcomings, how will they handle failure or tough feedback in the future?

Almost everyone can provide a meaningful assessment of personal shortcomings they’ve encountered while on the job and explain their key learnings from experience and how they applied them to avoid future issues. It’s especially helpful if an interviewee can articulate failures and learnings that pertain to their potential duties, demonstrating how they’re tuned in to your team’s needs.

Follow-up questions

  • How did you bounce back from the disappointment of that setback?
  • In retrospect, what would you have done differently to get a better outcome?
  • Do you think similar situations might come up in this role you’re interviewing for?

8. What measures do you take to communicate effectively with other team members?

Effective communication among remote team members requires a commitment to using varied techniques and tools. From chats to video conferencing and work management platforms, distributed teams must embrace multiple communication technologies.

This question allows interviewees to identify specific approaches (e.g., utilizing frequent one-on-one meetings) and general philosophies for strong communication among remote teams. Their answers will indicate their approach to working with others, shedding light on how they’ll ultimately perform.

Ask further questions to determine how effectively interviewees will likely communicate and collaborate. Ideally, they’ve used various tools to interact with team members, from traditional email to workplace communication and messaging tools such as Slack by Salesforce. An emphasis on over-communication and prioritizing consistency and clarity even at the risk of redundancy is usually a positive sign.  

Follow-up questions

  • Which communication and work management tools have you used previously?
  • When do you prefer asynchronous communication (such as email), and when would a video conference or phone call be preferable?

9. What is the key to managing your time and schedule?

The benefits of remote work include increased autonomy, independence, and flexibility, making effective time management, schedule adherence, and organization crucial skills for remote workers. Interviewees should have a proven track record of task prioritization and successful time management, demonstrating the ability to focus on the appropriate aspects of a job and complete assignments on time.

Follow-up questions

  • What tools and techniques do you use to stay organized, manage your time, and complete your work on time?
  • How do you identify potential problems that may disrupt your ability to turn in deliverables on time and help avoid unnecessary hold-ups?
  • If your tasks are dependent on others completing their work, how do you loop into the team to see if there are expected delays and determine how they might affect your schedule?

10. Describe a time when you had to provide difficult feedback. How did you communicate constructively?

It’s easy to demonstrate strong communication skills when everything is going well. But communication is particularly vital in challenging times when frank discussion and real solutions are warranted. This question gets at these difficult dialogues, allowing interviewees to showcase their skills in handling delicate situations.

For remote workers, it’s crucial to be effective and professional when communicating criticism or describing challenges. Because you’re not meeting in person, it’s easy to misinterpret a team member’s intentions or misunderstand what they hope to express. Hopefully, you can evaluate whether the interviewee will succeed in surmounting these hurdles.

Look for interviewees who offer a mature and insightful account of communicating challenging news. Ideally, they can identify how they chose to communicate the feedback or update and the specific tone they struck. Their account of the other people involved should be observant and respectful versus accusatory and petty. Otherwise, they might not be a team player. Challenge interviewees with more detailed questions such as those below.

Follow-up questions

  • How did you and your team communicate about the issue moving forward? What were later conversations like?
  • In retrospect, would you change anything about the way you communicated the issue?
  • What did you learn from that experience that might help you move forward?

11. How do you create strong engagement with other team members despite the physical distance?

Remote work requires a more intentional approach to cultivating camaraderie in contrast to the in-office experience. With team members only interacting virtually, professionals can feel isolated and starved for personal contact or a sense of participation in something larger than their project.

In answering this question, your interviewee can describe how they’ll utilize their people skills within your distributed workforce. Their response will also give you insight into who they are on a more personal level. Look for ways they create small but meaningful ways to bond and socialize, such as small talk at the beginning of meetings, participating in a group chat “break room” an employer created within a communications software application, or celebrating team members’ accomplishments.

At the same time, an interviewee should highlight their ability to maintain professional working relationships without overstepping boundaries. Ask further questions that allow them to describe their approach to team engagement and collaboration.

Follow-up questions

  • How would you describe your most effective working relationships? What made them successful?
  • Some people experience remote work as isolating. Do you think that will be a challenge, and how will you handle those feelings if they arise?

12. What do you like about the work you do?

Everyone should be able to convey things they love about their work. Answers can be very telling, highlighting an interviewee’s personality, potential cultural fit within your company, and what motivates them.

If their answer doesn’t include aspects of the job they’re interviewing for, they may not be a good fit. For example, if you’re looking to fill a customer support position and they didn’t include enjoying interacting with customers or troubling shooting, it could be a red flag. If they say they enjoy interacting or “hanging out” with coworkers, dig a little deeper to determine if remote work is right for this individual.

Also, be sure to get answers that pertain to remote work, such as the ability to take the dog for a walk during breaks. If they don’t include any, be prepared to ask additional questions.

Follow-up questions

  • What do you like most about your job when working remotely?
  • To what extent does the ability to interact with team members affect your job satisfaction, and what will you do to accomplish this as part of a remote, distributed team?
  • How does working remotely help you be successful in your job?

13. If hired, what steps do you plan to take to get off to a great start?

Great remote workers can leap into action without too much hand-holding. Often, that means getting up to speed through their own learning and immersing themselves in information relevant to their role.

You’re gauging how much thought they’ve given the role and their readiness to contribute quickly by asking this question. Their answers will also reveal how the interviewee’s approach might resonate or contrast with your team’s typical way of working. If they bring a different perspective to the table, it could be a breath of fresh air—but it’s important to understand this difference in advance.

Candidates to consider should proactively gather important details about the job in general and in context to remote work. Look for an emphasis on communication, collaboration, teamwork, and understanding their role within the framework of the team. You may need to pose a few open-ended questions to get them started.

Follow-up questions

  • What would you need from our team to get off to a great start?
  • Are there specific members of our team that could help you get the information and context you need?
  • What do you hope to accomplish in your first week of work?

14. Do you anticipate any technical challenges while working remotely?

Technical difficulties are the bane of distributed teams, causing unnecessary delays and frustration if not dealt with adequately. You want to know that your interviewee has the technical tools and know-how to collaborate successfully and won’t be overwhelmed by the platforms you use daily.

Sure, you can expect a learning curve to some extent. But if a worker can’t get comfortable with the digital tools that your team relies on, they can’t be expected to succeed. Similarly, if they don’t have a steady internet and the appropriate devices, they won’t be set up for success.

Successful remote workers tend to be technically confident and competent. They don’t need to have direct experience with the platforms you use but should express a willingness to learn quickly. Try to determine if they have the right setup and tools to succeed working from a home office, including a dedicated workspace at home and the ability to use software applications and various technologies comfortably and confidently.

Follow-up questions

  • Which platforms are you most comfortable with?
  • Are you generally comfortable learning new platforms or programs? What are some examples you’ve learned to use in the past?
  • If you have technical questions, are you comfortable finding instructions and solutions yourself?

15. What is your work-life balance like?

Job seekers identify having a better work-life balance as one of the primary reasons they want to work remotely. Yet recent research indicates that 29% of remote workers struggle to maintain a proper work-life balance and have reported higher stress.

In large part, this is due to a lack of separation between home and work. Interviewees should be able to convey how they achieve a healthy work-life balance and make it a priority. Ask follow-up questions that encourage interviewees to highlight how they achieve balance and avoid the potential stress and burnout of being “always-on” when they live and work in the same place.

Follow-up questions

  • What work productivity tools do you use to stay on schedule so work doesn’t creep into your personal time?
  • What kind of schedule do you create, and how do you establish boundaries?
  • Do you take breaks throughout the day?

16. Why do you want to work for this company?

Sure, this is a common question most every recruiter asks when prescreening a potential hire, but that doesn’t mean you shouldn’t ask it. You want someone who believes in your company’s products or services, its mission, and who will be a good fit into the company culture.

At the same time, gauge how important remote work plays into an interviewee’s desire to work for the company. If it’s their singular motivation, this could be a red flag depending on the type and level of job they’re seeking. Likewise, someone adamant about only remote working could spotlight a degree of inflexibility, depending on your industry and if potential job advancement trajectory could require an in-office presence. Follow with questions that help you see the whole picture.

Follow-up questions

  • How much does the ability to work remotely impact your desire to work for our company?
  • Is the potential for upward mobility in your current career path a key factor in your decision? (This answer could be important if promotion to higher-level jobs in their current career path may require in-office work full or part-time at your company.)
  • Would you be willing to work part of the week in-office and remotely the remaining days if our policy changes?

Next steps

By posing the questions suggested in this article, you can gauge any professional’s potential for success within your distributed team. As more companies embrace hybrid work models or a remote-first workplace, your capacity to assess workers along these lines will give you an essential edge when searching for top talent. Now, it’s time to find qualified remote professionals and give these questions a try.

Let Upwork take the hassle out of your talent hunt. Our platform makes it simple to access thousands of top independent professionals. In fact, you post the details of your project, and they bid to work for you. From there, you can engage them directly—and pick the professional who perfectly fits your remote team’s needs.


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