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How to Prepare for a Remote Job Search

By Joshua Kraus

Entrepreneur

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The number of people working remotely is at an all-time high, and that’s not just because telecommuting is pants-optional. By giving employees more control over their schedule and work environment, remote jobs can enhance the work-life balance that so many people struggle to maintain.

But if you’ve held in-house positions for most of your career, properly preparing for your remote job search can up your chances of impressing remote employers, nailing the interview, and landing a remote job that best fits your needs.

What Are Remote Employers Looking For?

Remote employers are looking for three things in particular.

Independence

The office may at times feel like a panopticonic prison, but there is something to be said for workplace accountability. Can you stay focused without a boss periodically checking in on you? Can you stay productive without the sight and sound of other co-workers clacking away on their computers? When you work from home, the Damocles of the deadline is blunted and the motivating effect of being in close proximity to your team members weakens.

Remote employers understand these challenges, which is why they look for candidates who can motivate themselves without external prompting. As trite as buzzwords like self-starter and proactive can be, they carry a significant amount of weight in the remote job search. Not only do you need to possess these qualities, you’ll need to be able demonstrate them to potential employers.

Communication

Working in an office allows employees to be more passive. Don’t know what’s going on? A co-worker can fill you in via a few seconds of conversation. Your boss is only a few steps away. Maybe there’s a whiteboard in the break room with announcements. Sharing a space with people just makes it much easier to stay in the loop.

But if you’re on your own, you need to take initiative. To compensate for the lack of face-to-face, a good remote worker will put effort into the virtual communication tools at their disposal. They’ll reach out to people through email or Slack. They’ll suggest video chats or calls to hash things out. Even swapping memes in a group chat can help you stay engaged. But if you give in to the temptation of solitude, communication could suffer, and so could your work.

Rational Thinking

When communicating primarily through text, it’s all too common for our imaginations to run wild with unfounded anxieties. Emailed your boss a question and they didn’t respond within whatever time frame you’ve arbitrarily decided was reasonable? They must think it’s a dumb question and you’re dumb for asking it. They must not deem you important enough to expediently respond to. They must be offended by something you wrote. Asked a co-worker to do something and they responded with “k”? They hate you. They’re telling everyone how much they hate you. Everyone hates you. You’re garbage!

Or … absolutely none of that is true and the coldness of non-verbal communication is messing with your head. Like any good employer, remote employers don’t want drama. They want rational critical thinkers who can vault the pitfalls of remote communication and maintain healthy work relationships. K?

How Do You Demonstrate These Skills On Your Resume?

Even if you have little to no remote work experience, there are ways to frame your in-house work experience so that it demonstrates remote work skills. What have you done that demonstrates independence? Communication? Rational thinking? Figure it out and integrate it into your resume.

For example, if you took the initiative on anything in a previous position, emphasize it. Say you independently devised and implemented project x or volunteered to plan, create, and maintain project y. Explain that you created and ran program z with little oversight.

Here are some other ideas to get you thinking:

  • You’re not highly motivated, you’re self-motivated
  • You didn’t work on a lot of projects, you balanced multiple projects simultaneously
  • You didn’t let clients know if their orders were going to be late, you proactively reached out to clients when their orders were going to be late.

Finding the Right Remote Job

Whatever your field of work, refrain from throwing your resume at every remote job opportunity to see what sticks. Have some dignity, for Pete’s sake! Like any job search, you have just as much right to be discerning as a potential employer, so before starting your search, establish what you’re looking for in a remote job so you can find one that fits your needs, work preferences, and desired lifestyle.

Here are some questions to ask yourself:

  • Am I looking for full-time work or freelance work? One might have benefits, one probably doesn’t. One is certainly more stable than the other, but then again, one is probably more flexible …
  • Do I want the opportunity to go into the office if I need to, or am I all right working for a company hundreds, if not thousands, of miles away? Many remote jobs offer the chance to periodically meet face to face. Others are too geographically dispersed to make that possible.
  • Do I want to work regular hours, or do I want something more flexible? Some remote jobs demand a traditional 9–5 schedule, while others let you work whenever you want as long as you get your work done. And then there are jobs that might demand you operate on a different time table entirely, such as those based in other countries, or those that need people to work odd hours and/or weekends.
  • What kind of work culture do I want? Some remote jobs are team-oriented and collaborative. Others treat you like a lone-wolf. Some companies keep mostly in-house employees with a few remote workers, and others, the opposite.

Nailing down these criteria helps focus your remote job search and improves the likelihood that you’ll find one that fits your needs. So keep these questions in mind when reviewing a job posting or reading about the company. Look at Glassdoor reviews or contact current or former employees and inquire about their experience. Remember, they need to be as good a fit for you as you are for them.

Prep for the Interview

A remote job interview will probably proceed similarly to an in-house job interview (what are your greatest strengths, where do you see yourself in five years, can there be ethical consumption under capitalism, and so on), but there are a few remote-specific gotcha questions to always look out for.

How will you stay motivated and productive without an in-person supervisor?

This is your opportunity to venture beyond the buzzword by inviting the interviewer into your inner sanctum. However you self-motivate — whether it’s listening to nature sounds and taking a ten-minute walk every two hours, relying on to-do lists and Pomodoro timers to stay on task, using website blockers to avoid distractions. Lay it all out for the interviewer to assure them that you can do the job without traditional oversight.

What would you do if there was an urgent issue but you can’t reach any members of your team?

This isn’t a hypothetical question. Something like this is bound to happen, and a remote employer wants to hear a few very specific responses.

  • You will remain calm, collected, and rational.
  • You will handle as much of the issue as you can on your own.
  • You will thoroughly document the issue for later analysis.
  • You will reach out to any stakeholders affected by the issue and assure them that steps are being taken to rectify it.

Why do you want to work remotely?

This question is really about two things: why you want to work a remote job, and why you want to work for this particular company.

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For part one, just be honest. The flexible schedule allows you to better balance your time. You want to be home for your dog, your kids, or because you’re renovating your house. You’re more comfortable in your own space. You don’t want to waste time commuting. Traditional hours don’t gel with your circadian rhythm. These are all completely legitimate reasons to work remotely, and any reasonable employer should find them perfectly sufficient.

For part two, answer as you would if this were an in-house job interview. If you’re excited about working for the company, great! If it really is just because you want to work remotely, find something about the company you appreciate and focus on that. You support their mission, you’ve heard good things about their work culture, you value their philanthropic efforts. Unless you’re applying to Halliburton, you can probably find something you like.

How are you going to communicate with your team?

Communication is vital in any job, so you can imagine the weight remote employers must place on it. Definitely touch on your favorite collaboration tools (Google Docs, Slack, carrier pigeon), but also discuss your communication style. What usually prompts you to check in with people? Is it only when there’s a problem? When you need something? Do you like structured, scheduled check-ins or are you more of an ad hoc kind of person? Do you like participating in ongoing group chats to stay engaged, ease stress, or strengthen relationships? Or are one-on-ones more your thing?

There is no right communication style (though there are plenty of wrong ones, cough cough inappropriate BCC behavior cough cough). Remote employees just want to hear that you understand the importance of communication, and have a solid plan of attack.

Takeaways for Your Remote Job Search

  • Remote employers are looking for independent workers who can take initiative, are self-motivated, and stay focused and engaged no matter where they’re working.
  • Remote employers need workers who aren’t just savvy with virtual communication tools, but who will put in the extra effort to check in with people, ask for help when they need it, and offer help when they’re asked.
  • Remote employers rely on rational people who won’t succumb to the self-sabotage of text-based communication.
  • To showcase your remote abilities, use your resume to highlight aspects of previous jobs that translate to remote work.
  • Before starting your remote job search, establish what kind of remote job will fit your needs.
  • Prepare for a remote job interview by anticipating remote-specific gotcha questions, all while keeping in mind that employers don’t just want to know why you want to work remotely, but why you want to work remotely for them.

Prepared for your remote job search? Head to SitePoint Remote to find your next role, where we handpick the best remote jobs for developers, designers, and digital professionals.

Josh Kraus is a Chicago-born, Denver-based writer and mediocre autobiographist with an interest in art, entrepreneurship, and emerging industries. When he's not writing, he attends to his t-shirt business, Bird Fur. Find him at joshkra.us and birdfurtees.com.

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