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6 Key Questions When Interviewing For Remote Jobs

by Chris Dyer

If you have been managing remote employees, you know that some people adapt quickly while others struggle to get into a groove. I believe that leaders have an obligation to help employees succeed, particularly existing employees who are transitioning to remote. But as you bring on new employees, you can screen for potential success in remote work. Here are six questions when interviewing for remote jobs and a few other ways to evaluate “remoteability.”

Interviewing For Remote Jobs: The Red Flags There are personality types who may not thrive in the remote world. You probably know people who fit these descriptions:

  • The person who walks in and commands the room through charisma or physical size. Charisma can come through in a video conference meeting, but not to the same extent it does in an in-person meeting.

  • The person who takes pride in knowing all the gossip, from office politics to personal information. I’m not saying that gossip is bad — Jennifer Haupt cites a study suggesting that office gossip can be positive (2015) — but the transition to remote will change the dynamic.

  • The person who thrives on being better than others — dressing better, eating at better restaurants, drinking better wine, etc. Of course, people can brag via your communications platform, but remote work compels people to stand out via results and performance, not designer clothes.

Questions These questions probe into characteristics that are valuable in both remote and brick-and-mortar arrangements. However, they are even more important in remote work, as people need to be able to perform at a high level with minimal direct supervision. As my coauthor Kim Shepherd and I argue in Remote Work: Redesign Processes, Practices and Strategies to Engage a Remote Workforce (2021), the best way to manage performance in this context is to establish and monitor goals and metrics. Note that these are all behavior-based questions — they ask for real-life examples and elicit a narrative answer.

1. Tell me about a recent work situation in which you had to use critical thinking skills. This question helps you assess a person’s ability to think through an issue. You want to hear how they identified and defined a problem, what resources they used, and what challenges they overcame in resolving the situation.

2. Thinking back over the past six months, what was your biggest time management challenge? Self-discipline is essential in remote work, and a lapse in discipline can throw off time management, prioritization and deadlines. Keep in mind that everyone works a little differently. Whatever their approach, the candidate should be able to tell you how they prioritize their days.

3. Describe a recent failure, mistake or misstep. In my book The Power of Company Culture: How Any Business Can Build a Culture that Improves Productivity, Performance and Profits (2018), “mistakes” is one of the seven pillars of culture success. Mistakes are going to happen. What you want to hear from the candidate is how they handled the situation, made it right and — most of all — how they turned it into a learning opportunity.

4. Describe a recent scenario that highlights your ability to achieve results independently. This is another area requiring self-discipline, along with self-motivation. I tend to be wary of candidates who say everything is always wonderful, so I might probe for an example of how a person overcame a lack of motivation to hit a deadline or other target. We all have days when we’d rather be doing something besides work, right?

5. Tell me about a recent situation that showcases your collaboration skills. This is the flip side of number 4, and just as important. Collaboration is harder in a remote model. What did the candidate do to ensure collaboration at a distance? Did they take proactive steps to include all stakeholders?

6. What tangible steps have you taken, while working at home, to maintain focus and attention? Remote workers are subject to multiple demands for attention, including children, pets, television and chores. You want to hear answers like, “I created a separate quiet office space” or “The family knows not to bother me while I’m working” or “The kids don’t come to me — instead, I check in with them every hour or so.”

OTHER ASSESSMENTS The following skills are also important, and you can embed assessments of them in your recruitment process.

Communication Just about every job posting out there asks for “excellent communication skills,” but those skills are truly indispensable in remote work. One reason is that, in a remote model, you often lose body language, facial expressions and intonation in most communication channels. You can evaluate this during video conference interviews, and by asking candidates to answer a question or two in writing.

Technical savvy If someone struggles with the technology to get into a video conference interview, it may be a bad sign. A candidate with high remoteability will take time in advance of the interview to make sure everything is good to go.

Following instructions Most likely your recruitment process already includes instructions that candidates must follow, such as asking them to schedule an interview or take a personality assessment. Good remote employees are self-reliant, and if simple instructions are a challenge, it might be a warning.

Responsiveness and proactivity How quickly does a candidate deliver what you ask for (such as completed forms) or reply to text or voicemail messages? This can tell you how responsive they may be as a remote employee. A standout candidate will demonstrate proactivity by providing more than you ask for or offering things (like references) before you ask.

KEEP AN OPEN MIND As with most candidate assessments, you shouldn’t consider any one of the above to be a deal-breaker. We’re all still getting used to this new reality, and most of these characteristics can be coached. Given the highly competitive nature of the talent market, your best candidates are the ones who tick MOST of the boxes.

References Dyer, C and Shepherd, K (2021) Remote Work: Redesign processes, practices and strategies to engage a remote workforce. Kogan Page, London.

Dyer, C (2018) The Power of Company Culture: How any business can build a culture that improves productivity, performance and profits. Kogan Page, London.

Haupt, J (2015) 5 Benefits of gossip (even negative gossip). Psychology Today, 22 June. Available from: [Last accessed December 15, 2021]


Chris Dyer is the founder and CEO of PeopleG2, where he manages 30 full-time remote employees and 3,000 independent contractors. PeopleG2 is routinely ranked as one of the best places to work and has been listed as one of Inc.’s 5000 Fastest-Growing Companies. Having made the transition to remote during the recession in 2009 with stunning success, Chris Dyer is now a world-renowned expert on remote leadership and productive company culture.

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