Four Steps to Securing a Remote Work Setup

Remote work setups and their variants are more common than you might realize.

This is especially true in the knowledge economy. The reason countless programmers, marketers, designers, customer service professionals etc. mainly work in the office is because either a) they simply don’t question it or b) their managers say so.

If surveys are to be believed, it’s usually the latter. Many more of us would take a more remote-friendly setup if it were offered.

Well, if “remote” is your preferred setup then I have some good news.

You can tailor your job search to suss out remote-first or remote-friendly positions.

It’s easier now today than ever before.

Telecommuting is slowly but steadily entering the mainstream. Getting a work from home setup is more is, nowadays, more realistic than ever. The bad news? If you’re determined to go in this direction, you’re going to have to work a bit harder than the average job applicant.

Now, the reason I’m writing this post is because I have a lot of personal experience in interviewing companies and evaluating their approach to remote work. Yes, companies don’t just interview me. I interview them. That’s what a job interview is supposed to be. My last job wasn’t advertised as remote however, I negotiated a contract and setup I wanted.

Now, I’d like to tell you how to do the same.

Step 1 Towards a Remote Work Setup – Start with research

Researching new roles can be exciting but it can also be draining. Very draining, depending on your current frame of mind. Approaching your research in a structured manner can do a lot of good. Viewing it as a project and setting aside a few hours each day for it will ensure you get one step closer to your goal.

When researching, you have several sources to tackle.

  • Job Boards: All job boards relevant to your industry, NOT just remote ones. In fact, avoid remote job boards for now and just focus on your industry, skills and experience. Generally speaking, I think almost all of them suck and are in a desperate need of an update. However, they are an excellent source and unfortunately the best we’ve got.
  • Companies: Research companies, research roles. Create a big Excel list. Look for words like “flexible working”, “mobile working”, “work-life balance”. Note down any remote or overtly remote-friendly companies too. This is a lot more fun and tolerable than just drawling through job boards.
  • Your Network: You don’t have a network yet? Start building one. This takes time but can pay off in the future. Be active on social media. You don’t have to be glued to my smartphone (mine is mainly a portable wifi router, if I’m honest…), but a certain level of consistency and connection can go a long way.

This is your starting point. Don’t stick only to these, either. Research local companies in your field and see if they mention anything about “work-life balance” on their ads, etc. See what open positions they currently have and start to dig deeper. Now, this of course brings me to my next point…

Step 2 – Research roles

You’ve gathered your sources, now it’s time to research specific roles and see where you could theoretically see yourself as a fit. Now you’ve got your sources, it is time to start looking for actual jobs within your field or skillset. Depending on your telecommute/work environment requirements, you may have quite a lot of options to choose from.

You can use standard job boards to suss out remote roles. In this case, it’s best to use a keyword combination such as “[JOB TITLE] + “remote””, “[JOB TITLE] + “telecommute””, “[JOB TITLE] + “home-based””, etc.

NOTE: Check out my post on how to find remote jobs with Indeed

Go through your list of target companies on a regular basis. Even if you don’t see an open position, see if you can send an open application.

Step 3 – Start a Conversation

If you phone/email to ask a company about their policy, you’ve already started a conversation. If the answer is what you’re looking for, send a CV along or apply. Cover letters are just that: an icebreaker that introduces your experience to a company. If anything, it is a sales letter.

Depending on the feel you get for a company, it might be pertinent to ask about their work setup. Is the role office-based, but with a certain degree of flexibility? Do they only want you to be there now and then? These distinct, unfortunately, are not always clear on job advertisements. It’s annoying, yes, but there’s no harm in asking.

NOTE: When asking about location flexibility with specific roles, make sure to tie it in with further questions about the work in general. You’re not just looking for any old flexible job: you’re also looking for the next step in your career. You want to show your passion, motivation and how working remotely can actually help you achieve that.


Step 4 – Start to negotiate

If you get to the next step of the hiring process, congratulations! Your work environment will often depend on the team you’re working with and your manager. It is in this interview that you now have the chance to…

  • Gauge what the company culture is really like. Do a lot of people work remotely, even some of the time? How used to communicating over Slack/Skype/video are your potential colleagues? Ask the right probing questions, as well as questions about the role.
  • Find out what terms and conditions you can put in the contract. What setups do other people have? Do some people work part time?


Finding work isn’t easy. It can be a long, hard slog and in terms of job interviews, you may kiss a lot of frogs (hopefully not literally…). You will also interview companies where you think, “Yes… This is it!” only to be rejected in favour of a candidate who may have slightly more experience or one extra skill than you.

Whatever it is, and whatever work environment you’re looking for (remote or not), you need to remember that ultimately it is up to you to get a setup that you want. There are more jobs out there than you think.