Five questions to ask candidates for remote work.

Here are our top questions to ask candidates for off-site jobs…

1. Have you worked remotely before?

Obvious as it may seem, getting this in early achieves two key things: “Yes” allows you to move on to other areas around skills, tools and past experiences.

A “No” means you need to take a little more time to establish that they have the right mindset for telecommuting. Follow up with questions like “How do you expect your work routines to change?” and “Why do you think remote working will work for you?” You’re looking for someone who’s thought this through, not someone who’s just had enough of sitting in traffic in the morning. A great candidate for the role may not be the best fit for remote working – adjustment periods are fine; what you don’t want is someone who finds out they don’t like being alone for much of the day three months into the job.

Finally, “Why do you want to work remotely?” should prompt a good prospect to tell you why they do their best work under their own steam, not just wax lyrical about how it will improve their life generally.

2. How do you schedule your day?

Answers to this should tell you a lot about how someone stays focused, productive and motivated when no one’s looking. Good candidates will be able to talk in terms of priorities, handling the inevitable distractions and managing tasks.

If flexi-time or shift work on a global team are options, this question will help you figure out whether the candidate’s lifestyle meets your team requirements – are they night owls or early risers? Do they take a couple of hours in the early afternoon to collect the kids from school? If it fits in with your needs and time zones, someone mature enough to understand when they’re at their best will work well.

3. How would you handle a situation where a project you’re managing or working on is falling behind schedule?

The best remote workers are self-reliant and motivated – but they’re also responsible and proactive. This includes knowing when to flag potential problems or admit you’re getting a little off schedule – both of which can happen when you’re not in the same building as your co-workers, who won’t necessarily notice if you’re struggling.

Self-guided problem solvers make great telecommuters – but they also know they don’t have to solve every single issue on their own, potentially putting projects or co-workers at risk. Hire candidates who have a strategy for handling curveballs, the confidence to admit when they’re struggling and the ability to find solutions. A responsible, “manage expectations” notification gives everyone on the team time to work around any issues.

4. Your manager/team is offline and there’s a problem. What will you do?

Everyone hits last-minute issues. Remote workers need to have the confidence, judgement and resourcefulness to make decisions independently when there are problems or challenges and no one else is online.

Look for candidates capable of taking on what they can to keep things moving, who communicate with relevant team members – and know when something’s urgent enough for an out-of-hours call. Candidates who know how to build relationships with co-workers outside their team will also be able to call in the cavalry for advice or company guidelines in similar situations.

5. What tools for communication and collaboration at work have you used?

Experienced off-site workers will tell you it’s a ‘horses for courses’ thing – email for issues you need to get in writing or aren’t urgent (deadlines, for example), Skype/instant messaging for quick questions and Slack/Basecamp for streamed group chats, brainstorming or the all-important socializing.

Ultimately, it’s not the specific tools that matter so much as a candidate’s understanding of the importance of communication. A good remote worker understands the practicalities of conducting, say, a code review via email, GoToMeeting, screenshare…You should be looking for someone who’s figured out what’s most effective for the situation they’re in.


Bootcamp founders Jason Fried and David Heinemeier Hansson say in their book Remote: Office Not Required, “Great remote workers are simply great workers. They exhibit two key qualities…smart and gets things done.” Once you’ve established that a promising candidate is the right fit for working remotely, you’re really just back to ensuring they’ve got the skills you need.

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