Want A Remote Job? Here Are 18 Interview Questions You Need to Be Prepared To Answer

By Randle Browning

Do you remember the days when selling Avon, entering data into spreadsheets, and answering customer service calls were the only options for people who wanted to work without spending 40+ hours a week at the office? Well, those days are gone.

Don’t get me wrong – jobs like those have done their part in making it possible for more of us to earn a living without driving to a traditional office every day. But these days, you can find a remote job in almost any field.

In the last decade, remote work has exploded in popularity. With technologies like HipChat, Google Drive, and video chat making it so simple to connect and collaborate online, it’s totally feasible to land a lucrative, fulfilling career without selling your soul to the daily commute or sending your kids to daycare for 10 hours a day.

And with remote workers (like Sondra and Jeremy Orozco on the oDesk blog) adopting titles like “digital nomad,” it’s clear that remote work doesn’t just mean clocking in from your home office. Remote workers travel the world, set their own hours, and rarely feel tied to a cubicle.

Alright, so I’m guessing I’ve sold you on the life of the remote worker. But if you’ve been working in a more traditional job or you’ve been out of the workforce for several years, the prospect of landing a remote job might seem overwhelming.

If you need some guidance on where to find remote job listings, check out this awesome post by Skillcrush’s own Leslie Zaikis: 25 Sites for Landing Remote Work.

But it’s not just about applying for the job. Before every dream job, there’s a terrifying perfectly doable job interview. And interviews for remote jobs come with their own set of pitfalls.

When you’re interviewing for a remote job, you won’t just be getting the usual questions – Can you describe yourself using 3 adjectives? When was a time you had to take the ethical high road? (← Real questions I got in job interviews.)

You’ll also have to field questions on how you’re going to handle the logistics of working outside the office, from working with your team members to managing your workload and communicating with your boss.

I know, it can be overwhelming. But I’ve got you covered.

In this article, you’ll find out:

• How to shift your mindset so you can ACE a remote job interview
• 18 top remote job interview questions you should know how to answer
• 18 ACTUAL answers to those questions from the Skillcrush team
• A FREE download to complete before you go into an interview for a remote job.

A remote job is different from a traditional job in the office: You’re trading the conference room for the video hangout, the closed door for the “away” message, the quick conversation for the digital chat, and your fluorescent lights for…well, for any kind of lighting you want.

And when you move away from your company, you gain freedom and control to plan your schedule and your work habits in a way that works for YOU.

But you trade that freedom for more responsibility. Without your boss walking by and the office manager checking your timesheet, it’s up to YOU to get your work done. That means you need to be an absolute pro at managing your time, prioritizing tasks, and communicating with your boss and coworkers.

Even so, Jason Fried and David Heinemeier Hansson of 37signals say in their recent book on the topic, “Remote work pulls back the curtain and exposes what was always the case, but not always appreciated or apparent: Great workers are simply great workers. They exhibit two key qualities, as Joel Spolsky labeled them in his ‘Guerrilla Guide to Interviewing’: Smart, and Get Things Done.”

In other words, if you’re a high achiever, you can be a high achiever anywhere.

But being able to be smart about your job and get things done depends on an important factor – how well do you know yourself? How well do you know what you need to succeed?

Meghan M. Biro of TalentCulture writes on the topic of telecommuting, “Here, as elsewhere in the world of work, two principles prevail: know thyself, and know thy culture.”

And it just so turns out that knowing yourself is ALSO the key to success in an interview for a remote job.

To convince your future boss that you are cut out for remote work, you need to understand exactly WHAT habits and characteristics make you qualified. And I mean really understand yourself, from the way you keep track of deadlines to the way you prepare for meetings – the nitty gritty of how you work and what makes you most effective.

And when it comes to being the “right fit” for a remote job, it’s not so much about measuring up as it is about knowing how to make yourself the most productive and fruitful version of yourself.

Shala Burroughs, Co-Founder of CloudPeeps (and remote worker and advisor to many other remote workers) says, “Be self-aware of the way you work, your strengths, etc. If you’re not, you have a world of hurt ahead of you. If you tell someone what you think they want to hear instead of what’s true, you’re setting yourself up for tremendous hurt and friction.”

Burroughs also says that employers are likely to ask remote candidates questions like, “What is your working style? When in the day do you switch on and start actually working? During which hours do you work optimally? Are you a night owl? A morning position? Remote positions can often account for that, and benefit from it.”

And employers want to know because those are the questions that really determine how well you’ll do your job and fit into the team.

In interviews for remote jobs, you’re FAR more likely to get questions about how you function on a daily basis than how big your dreams are. You’re more likely to be asked if you use Google Calendar than how you would describe yourself in 3 adjectives, and you probably won’t get asked a lot of hypotheticals.

Employers want to know about the logistics because in a remote job, when you can’t waltz into a coworker’s office to sort something out, little things – like how you communicate problems – make a big difference.

The takeaways? Sure, you’re going to have to show that you are smart and that you can do the job. But you’ll ALSO have to prove that you can handle (and excel in!) the conditions of a remote job, down to the little details.

Here at Skillcrush, where we’re entirely remote, I talked to our very own hiring managers and got REAL questions they’ve asked job candidates. AND I got real-life answers from the Skillcrush team (the ones who aced the interviews!!):

Here’s what this question is asking: When do you get focused and start working in earnest? What are the hours that you work optimally? Are you a night owl? A morning bird?

Remote teams can be made up of people working different shifts and all around the world so you won’t necessarily be stuck in the 9-to-5 if that’s not your thing. And remote jobs are often flexible as far as day-to-day routines are concerned. So you can also arrange your work in the way that’s best for you – as long as you get it all done.

So, take an honest look at what your natural rhythm is and how you’re most productive before you answer this question.

Kelli Orrela, Skillcrush Customer Service Manager and content creator, says: “I’m the type who leaps out of bed and gets straight to work. (Annoying, ain’t it!) I start my day by checking email for any urgent situations; then I take care of my daily tasks; and then I move on to either writing or working on long-term projects. I tend to save meetings or collaborative work for later in the day – both because it energizes me at the time when I might otherwise be “slumping” and because it helps accommodate the different time zones of our international remote team members.”

Kelli’s answer shows she knows when and how she’ll be the most productive, and that means dollar signs to the employer, who doesn’t want to waste time or money on remote workers who are inefficient. Plus, she shows a level of what I like to call “geographical sensitivity” for her teammates. In other words, she’s willing to be flexible and not schedule a meeting at 4:00 am New York time, even if it’s 11:00 am for her.

When you work on a remote team, there’s no chance to chat in the hall between meetings or catch up on the latest project during a shared ride to the office. So virtual communication will be absolutely fundamental to you getting your job done. And you’ll be using all kinds of tools to communicate – email, online chat, video hangouts, project management software, etc.

By asking this question about the tools and situations, your interviewer wants to know if you are familiar with them and savvy about what to use when.

Leslie Zaikis, Director of Sales and Marketing here at Skillcrush says: “I use email to confirm things I need in writing or want to reference later – like deadlines, schedules, or informal agreements. But, if I have just a quick question for another team member, I hop on chat to ask. And I love video hangouts for meetings, brainstorming, project kick-offs, or new team member orientation. It makes it so much easier to interpret the tone of a meeting and the priority of the project.”

Leslie’s answer shows that she gets how different communication platforms can serve her in different ways. Plus, it shows she knows what works best for collaborating with others. Setting deadlines in a chat that disappears? Not so much. Brainstorming on 50+ message email chain? No thank you. She knows how to use the tools that make remote work possible – and in the most efficient ways.

A lot of people want remote work because of the flexibility it allows. You can work from anywhere and at any time of day.

The boss wants to know: Are you going to be in a coworking space, your home office, a coffee shop, the library, a hotel room?

It’s important because it determines how you’ll fit into the team. Do you spend time with the kids every day between 3 and 5? Or maybe you work from home and you’re pretty much “on call” throughout the day.

I’ll take this one!

Randle Browning, Director of Content at Skillcrush, says: “I used to think that I would LOVE being able to spend my days working from coffee shops. But after working remotely for several months, I realized that working from home makes me way more effective. At a coffee shop (or other public place), you don’t always have control over “break time.” Maybe someone takes your outlet, the WIFI goes out, or people keep starting conversations with you. At home, things come up, but it’s a lot easier to get in the zone and STAY in the zone. Now I head to coffee shops when I can sense a case of cabin fever coming on.

As for schedule, I find that working in 2 or 3 long shifts is the best for me. I’ll work for 3-4 hours in the morning, then take a 2-3 hour break, then put in another block of hours. I don’t mind working past dinner time, and I’m much more productive in the afternoon if I take a break to get some sunshine in the midday.”

Showing that I know when and where I work best is a good sign for an employer. It means I’m unlikely to end up having a panic attack in a coffee shop when the spotty WIFI dropped my webinar broadcast. It makes me scared even thinking about it!

With this question, companies are both looking to see what equipment they might need to provide you with and checking on how aware you are about what working remotely might mean for you physically and logistically.

As Jason Fried says in 37signal’s book “Remote: Office Not Required”, “Working from home gives you the freedom to work wherever you want. Maybe you start at the kitchen counter, continue on the couch, and, if the weather is nice and you have a garden, finish up outside while enjoying the sunshine.”

But, as Fried goes on to say, wherever you work from, you need to make sure you have the essential basics. So, figure out what that is for you – A standing desk? A large monitor? Or maybe even an office in a coworking space?

Sara Regan, teaching assistant at Skillcrush says: “I like to change it up when it comes to my working environment. At my home office, I have both a sitting and a standing option so I can switch depending on the situation (standing for work at my makeshift standing desk, sitting for office hours and online meetings). I don’t need music to work, but some ambience is OK. And sometimes I even invite other devs to come over and cowork.”

When bosses can’t see their employees, they have to be doubly aware of how they’re getting on. It’s easy to see if your employee is uncomfortable or ill if you can watch them hobble from their chair to the copier, but, if you’re communicating digitally, it’s not so simple. Sara shows she is covered when it comes to taking care of both her physical and mental health.

Several years ago, I was working on a team to plan a big event. My supervisor had us all doing team building before the big day. One of our activities was to figure out how each of us processes information. We learned that some of us were “big picture” people – we could only finish tasks if we understood the whole project – while others only needed to know one thing: what’s due when?

And that matters to a remote manager. If Sally can’t operate without all of the facts, but Shana gets majorly overwhelmed when you give her more than she needs to know to complete a task, it can quickly send the whole team into shambles.

Knowing how you process information – what you need to know when and in what format – is incredibly valuable information.

Me again! Randle says: “If you can be an information hoarder, I am one. I do my best work when I understand the goals behind a project, its scope, and the whole big picture. I get the most ideas (and ideas are important in content) when I can picture how my work fits into the grand scheme. I know it can be a weakness, especially if I’m not the team leader on a certain project, so I try to ask key questions that will get me in the zone – questions like, What problem are we solving with this project? and What is our marker of success?”

The way you process information, you can probably see, isn’t just valuable knowledge for your boss. Your coworkers will understand you (and why you keep asking them to see the data) if they know how you hold all the threads together in your head.

Or you might get even more specific questions, like:

• What goes on your calendar?
• Do you schedule blocks of time to do certain kinds of work?
• Do you have an open calendar everyone can see?

Believe it or not, the logistics of how you organize your work life is CRUCIAL in a remote job. On the Skillcrush team, we love sharing our Google calendars so you kind of have to be on board with that. The same holds up with other companies and their preferred apps and platforms. Also, asking this question will reveal whether or not a candidate has put a lot of thought into organization, and in remote life, organization is a must.

Caroline Griffin, Class Manager at Skillcrush, says: “The key for me has always been to have one calendar and then organize the heck out of it. For the last few years, I’ve used a handful of calendars inside of iCal. I have color-coded ones for errands, my day job, freelance work, as well as fun stuff, bills, etc. I like it mainly because of how fast and seamless the sync is between my laptop and phone.

When I joined Skillcrush, I replaced my “day job” calendar with our Google Calendar, which has been a little less seamless but still works fine. I understand why people keep their work and personal calendars separate but that’s just never worked for me. I need everything in one place—synced across my devices and preferably color coded. I’m all about the color coding!”

Just like your systems for scheduling, the way you keep track of files and other information is really important. After all, it’s all digital! So, you can just drop virtual files on your coworker’s virtual desk if you need to share info with them. But the files need to be named and organized clearly so you’re not spreading “digital clutter” or losing track of data.

Before you go into a remote job interview, you should have a system for: organizing and storing files, keeping track of links, and handling issues like tab city (it’s my term for the situation in which you have 35 tabs open and you keep adding more until your browser crashes).

Caro says: “I keep everything in a local version of Dropbox… and I do mean everything. I love it because my backups are otherwise pretty irregular and this way I never have to worry about having the right version of a file. And I can access anything from my phone or a friends computer! I have a general “Projects” folder in there with subfolders for everything I’m currently working on as well as an Archive folder. When I finish a project, I just move its folder into the Archive. Then I always know exactly where something is when an old client comes calling.

I use the bookmark bar in Chrome to quickly access all the websites I use on the regular. But obviously we use a lot of Google Docs and that bookmark bar is only so wide. So one of those links is to a “Table of Contents” that has links to all of my frequently used documents and spreadsheets. (This is actually a trick I stole from Leslie!)

Also, this is only kind of related but the Todoist app has revolution my life and the way I organize my life. The desktop and mobile apps are good but they have an extension for Gmail that is a.maz.ing.”

The day I watched Marie Forleo’s video on separating tasks into Important versus Urgent, my life changed. Not ALL remote jobs are at fast-paced startups, but a lot of them are.

And, in that kind of working environment, it’s easy to get overwhelmed and feel like there is JUST too much to finish. That’s why it’s so important to be able to prioritize tasks. I kept staring at my to-do list thinking…ALL of these things need to happen. How can I prioritize?

Marie says to classify your to-do list with “I” and “U” for important or urgent tasks and do the important ones first. You always finish urgent things on time anyway because they’re urgent! So, make the most of your brain power and use your energy on the important things.

That ability to prioritize can make or break your success in a remote job, and employers need to know that you have an absolute handle on it.

Emily, Lead Developer at Skillcrush, says: “I prioritize tasks based on the business need / benefit. Tasks, projects and bug fixes that facilitate getting and converting new leads and those that have a direct and positive impact on students’ experience while on our site always take precedence.”

Just as communication is crucial when you work remotely, meetings are also huge. Because you won’t have those chance encounters in the elevator or informal conversations in the lunch room, you have to take full advantage of the limited time you do have during video or phone meetings with team members. And your future employer wants to know that you know how to do that.

Leslie says: “My top tips for remote meetings are:

• Always create an agenda. Without an agenda, meetings can go awry fast.
• Stay on time as much as possible. When you have two-hour long meetings, it can be easy to dread them!
• Do time checks with 15 minutes to go before the end of the meeting to stay on track and then 5 minutes to go to define next steps.
• Ask everyone for their input. Just like in a real meeting, sometimes people can hang back and not add their perspective so do a “round robin” to ask everyone to contribute to the conversation!!”

And, if you want to really impress your future remote employer when you answer this question – and in your remote interview in general, don’t miss Leslie’s fantastic blog post “Tech Tips for a Stress-free Video Interview”.

This is a great question because it shows your comfort level with tech, which is so important for a remote worker because you simply have to use tech to work remotely. And it also shows some of your personality and outside interests, which is one way a company can gauge how you’ll fit into a team.

For this answer, think about how technology is incorporated into your life and how you use it to make your life easier or better. That can be devices, apps, workflows, or even entertainment. So, mention your undying devotion to your MacBook Air or your obsession with podcast apps. Or explain how you keep on top of everything with a to-do list app, or how you keep your social media smooth as butter with IF and ThinkUp.

Lizu, Designer at Skillcrush says: “When I have lots of work for many projects, I simply make notes in an app on my phone. Also we use an Excel sheet to track many hours we work on each projects, the location of the projects, comments, etc. Sometimes, I also get information about projects in Pivotal Tracker. And, to communicate with the team, I use Google+ Hangouts video and chat and Gmail.

In my free time I like to take pictures, so I use my DSLR a lot. There are very nice subjects here in Nepal, plus the landscapes are great. I like color and contrast, and, after a photo session, I use programs like Photoshop or LightRoom to make my images come alive.”

It might seem a bit vague and general, but the reason you might get asked a question like this is because your potential employer wants to get a handle on your management skills. When you’re a remote worker, you’ll have to organize and coordinate projects differently than you would in person, so bear that in mind when you reply to this.

Leslie says: “For project management, I use video meetings to check in on status and adjust schedules. I also make project plan and scoping documents and share them with our remote team in Google Drive so everyone has access to all information. And I use project management systems like Trello, Basecamp, or Asana for larger projects.”

One of the biggest concerns of remote team leaders is trust. Your boss needs to KNOW that you can handle managing a project, from wrangling your teammates to meeting the deadline. Leslie shows that she has the tech chops AND the organization skills to be the leader of her own projects, so her boss won’t have to check on her 100 times a day to be sure she’s getting the work done.

Look, technology connects people and makes it possible to work on a team without ever seeing them IRL, but sometimes it requires some special finesse. Chat doesn’t always convey tone, and sometimes wires get crossed.

Hiring managers want to see that you have a plan for how to untangle them when they do.

The one and only Adda Birnir, Founder and CEO at Skillcrush, says: “Hop on a Google Hangout!! I find that there is a lot of inertia around getting on a video hangout, but really there is nothing that compares.

Basically I think that when you work remote you need to use something like Hipchat to be in touch on the regular, you should do video hangouts at least a few times a week, and if not video hangouts, get on the phone! There is just nothing that compares to talking it out.”

I know it’s counterintuitive, but employers want to know that you are available and ready to do what it takes to communicate with your team, whether that means getting on an unexpected video call or brainstorming in a group chat.

Even with a great team behind you, you have to take care of your physical and mental health as a remote worker more than you would in a regular office gig. Like I said, it’s not easy for coworkers or bosses to notice the outward symptoms of problems. They don’t see you sitting at your computer until all hours or notice you dragging when you used to be full of energy.

That means you have to take care of you! That includes getting enough rest and exercise, setting boundaries between your work life and your personal life, making sure you get the social contact you need, and remembering not to neglect your interests outside of work.

Kelli says: “I’m lucky I have a hobby that’s super social so it’s a great balance to my remote working. And I’ve learned that I’m incredibly more effective when I’ve gotten enough sleep and some exercise. I know I have to sometimes just ‘call it a night’ or go for a run – no matter how much work there is to be done.”

::cough:: Country line dancing! Her hobby is country line dancing! ::cough::

Did you say something?

Anyway… Do you know what remote team managers dread more than inefficiency? Employee burnout! The only thing worse than a worker dragging her heels is a worker who’s rocking in the corner in fear of opening her laptop. In Kelli’s answer, she’s showing the potential boss that she knows how to prioritize tasks, realizes her limits, and can decide when it’s actually MORE efficient to take a break than slog on.

As a remote worker, it’s easy to run into a problem and feel like you have to solve it on your own. And, because you’re not sitting in the same office as your team, you can get off schedule or overwhelmed without anyone else noticing.

With this question, your future employer is hoping to see your strategies for proactively preventing this situation by letting your co-workers and even your boss know when you need help so that you don’t put yourself or your team at risk.

Kelli says: “I encourage anyone who’s remote to speak up as soon as you notice that things aren’t going as planned. That doesn’t mean complaining or panicking – just giving a “heads-up” that the project is a day or two behind schedule or that one of your designers came down with the flu and can’t finish the blog post design today. That gives everyone a chance to find solutions and adjust plans before it’s too late.”

And, speaking of solutions, instead of just letting your boss know that there’s a problem, why not offer a solution as well? So, before you inform her about your designer’s flu, get in touch with your other designer and see if she can step in. Or propose that you move another post up in the schedule so that this one can wait. Remember, one of the most important qualities of a remote worker is being able to take responsibility. Part of that is finding a solution, not JUST reporting the problem.

No matter how much planning you do in advance, or how organized your files are, or even how precisely the team followed the project plan, sometimes things go wrong.

When things go awry on a remote team, that can often mean that you’re stuck making important decisions on your own. When an employer asks you this question, she wants to know if you have the resourcefulness and judgement to make independent decisions when you have to.

Aisha Souto-Maior, Lead Designer at Skillcrush, says: “I generally do everything within my power to address the problem on my own, and sometimes that means solving about 50% of the problem until I hit a wall where it’s beyond my reach. When that happens, I fix as much as I can and make sure that I’ve gotten in touch with all the team members involved, and sometimes that means through email, text, phone calls and instant messaging (for those really urgent problems!). When it’s strictly design related, that’s when I fall back on our brand guidelines to help find the best design solutions in a crunch.”

Not everyone goes remote for the same reason. Some people are caregivers or stay-at-home moms. Others have health conditions that keep them out of the office. Still others might be geographically challenged (that’s me!), as in, you live in a place that makes it geographically impossible to work in the job you want. Or maybe you just want to travel the world without quitting your full-time job.

When you get this question, it’s easy to jump into all the reasons remote work is going to make YOUR life better. And you should definitely tell the boss what special life circumstances are keeping you out of the office. But you’ll really wow the hiring manager if you can tell not JUST why remote work is going to improve your life, but why you do your best work remotely. In other words, explain how working remotely makes you shine and makes you a smarter, more effective, and more efficient employee.

Randle (c’est moi!) says: “I moved to back to Waco after graduate school because my husband and I opened a pizza restaurant here. But I quickly realized that all of my training and experience had set me up to work in a big city – I had cooked in professional kitchens, taught writing, and managed arts events. And I wanted to work in an exciting, fast-paced environment, and this town is pretty industrial.

But aside from my geographical situation, I know that I work best in a remote setting because I’m most productive if I take breaks throughout the day to exercise or sit on the porch for 15 minutes. Plus I tend to do some of my most focused work in the evening, when all distraction is gone. That’s much easier to do when my office is upstairs rather than across town!”

RELATED: 50 of the Best Companies Hiring Remote Workers

Knowing yourself means knowing areas you can improve. When your employer asks you about your biggest concerns, she wants to know two things: (1) are you aware of your weaknesses and prepared to watch out for them, and (2) how can she make sure not to put you in a lot of situations that prey on those weaknesses.

And remember the central tenet of remote work: know thyself.

Aisha says: “My biggest struggle working remotely is generally finding the right balance of quiet time to get the work done and enough time with team so that there is a good amount of communication, sometimes I get it just right and sometimes I find myself trying to catch up in one of those areas. Also, when you love what you do (like I do!) it can be tempting to work all day when you’re in the comfort of your own home, but you need to set your schedule and stick to it, if not your energy and WORK will suffer.”

Ahh, the big finish! And it’s an interview classic: Your greatest strength. But, in the case of this question, there’s a remote twist.

When you answer this, let the company know what remote working superpowers you’ll be wielding, or what amazing experience you have that will make you EXACTLY the person they need on their team.

Deepina Kapila, Instructor and Social Media Manager at Skillcrush says: “My most valuable asset is my suite of mobile tech tools and gadgets! Without these tools, my life would be significantly more complicated – even the simplest task would take twice the amount of time. I make it a point to stay on top of technology tools that support the modern, mobile career. My entire life is in the cloud where it’s secure (!) but enables my work across devices and locations.”

RELATED: The 25 Best Sites For Finding Remote Work

Whatever your secret remote weapon, working style, office set-up, or ideal daily schedule is, you’ll need to really think it through before your remote job interview. Practicing how you’ll respond is important when going for any job interview but especially so when it comes to remote work. The logistics of the interview itself and the increased demands on you to be independent, extra communicative, and technically adept won’t leave you much time for beating around the bush.

And what to do once you land the job? Well that’s a different post. 😉