The Ultimate Guide To Hiring Remote Workers

My first software business was built on the basis of hiring remote workers. To put it bluntly, without outsourced labor, there would never have been a NinjaOutreach, or a successful exit.

As a bootstrapped startup, we simply didn’t have the resources to hire American workers and pay their salaries, health care, and benefits. It just wasn’t feasible.

Over the years I have gotten extremely comfortable hiring and working with individuals from countries all over the world. Even now, I work with developers in Argentina, marketers in Ukraine, and writers in Singapore.

Now, I’ll show you how you can do the same.

1. Hiring Remote Workers: Cliffs Notes

2. Why You Should Start Hiring Remote Workers, Stat.

  1. Amazing Cost Savings (Ka-ching!)
  2. Higher Retention Rates (And Less Folks Who Quit On You)
  3. Access To Higher Quality Talent (AKA The Cream Of The Crop)
  4. Diversify Your Team (And Watch As Effectiveness Skyrockets)

3. Where Are All The Remote Workers At?

4. Writing A Kickass Job Description To Attract Talent

  1. Include Reference Material
  2. Weed Out Canned Responses

5. Screening Candidates: Separating The Wheat From The Chaff

  1. Interview Questions To Ask Remote Workers
  2. Looking At Past Feedback & Portfolios

6. How Much Should I Pay My Freelancers?

  1. Per Hour Jobs VS Fixed Price Jobs: Which Is Better?
  2. Determining Your Budget (Without Plucking A Number Out Of Thin Air)
  3. Cheap, Fast, and Good: Pick Two

7. The Trial Period (Test-Drive Before You Commit!)

8. How NOT To Manage Your Remote Team

  1. Having Multiple Points Of Contact (That Shit Is Confusing)
  2. Giving Too Little Direction (Your Guidance Is Needed!)
  3. Delaying Payments (Don’t Be That Guy)
  4. Expecting Too Much (While Paying Peanuts)

Your Action List For Hiring Remote Workers

Hiring Remote Workers: Cliffs Notes

You should hire remote workers because:

  • You can save up to $47,534 per year per employee
  • You experience 25% less employee turnover
  • You get access to higher quality talent
  • You can diversify your team (which results in more innovation and more accurate decision-making)


Where do you hire remote workers?

Upwork, Fiverr, PeoplePerHour, Freelancer, and 99Designs. And ask around!

How to write a kickass job description that attracts talent:

  • Link to your website so that your candidates have a better idea of what your company does (if not, at least share your industry)
  • Include a comprehensive outline of your specifications and requirements
  • Include references so your candidates can envision how you want your end product
  • Ask questions to weed out canned responses

How to screen remote workers:

  • Interview them
  • Look at their past clients’ feedback and portfolio

Questions to ask when interviewing remote workers:

  • What is your longest-standing client account?
  • Are you freelancing on a part-time or a full-time basis?
  • Can you meet my deadline?
  • How do you approach your projects?
  • What type of clients do you like to work with?
  • Do you have any questions about the project?

Should you pay per hour or a fixed price?

Per-hour works for jobs with undefined scopes, and fixed price works for jobs which come with specific deliverables.

How to determine your budget:

  • Think about how much hiring a full-timer would cost you
  • Break it down to an hourly rate
  • Take this as a baseline, and budget for more (remote workers charge more to make up for the lack of healthcare and benefits)
  • If you’re using Upwork, check out their guidelines based on job title
  • Take other criteria (short turnaround times, related degrees or education, etc) into consideration

Before you commit to a remote hire:

Set up a trial so that you can evaluate your top few candidates more thoroughly.

Mistakes that business owners make when managing their remote teams:

  • Having multiple points of contact
  • Giving too little direction
  • Delaying payment
  • Expecting too much

Your action list for hiring remote workers:

  • Decide what positions you want to fill with remote workers
  • Research on which countries have the best talent with the skill sets you need
  • Decide on your budget
  • Write a kickass job ad, and post it on sites such as Upwork
  • Screen and interview all applicants
  • Set up a trial test for the best candidates
  • Avoid the above-mentioned pitfalls when managing your remote workers

Why You Should Start Hiring Remote Workers, Stat.

Not because it’s trendy. Not because you want to be able to get away with spending the bulk of your workday in your PJs. But because of the…

Amazing Cost Savings (Ka-ching!)

Hiring remote workers makes a ton of financial sense.

Consider this: the average real estate cost per employee is a whopping $10,000 per year.

Total savings: $10,000

Then there’s also the fact that unscheduled absences cost employers $1,800 per employee per year, and that companies with a remote working program report 63% fewer unscheduled absences.

This means you’re saving $1,134 per year per employee.

Total savings: $11,134

Now, let’s talk about cheap labour.

If you’re trying to hire a software developer based in Silicon Valley, you can expect to pay roughly $112,000 per year.

Let’s say you widen your search to Denver. Over there, software developers command just $75,600 on average.

But why stop at Denver? You might as well go the whole hog, and open up the job opportunity to developers in Europe. In place such as Russia, Ukraine and Romania, the average pay for a software developer is just $15,000 to $20,000.

I’m going to take a conservative estimate here, and assume that you hire a candidate from Denver instead of someone based in Russia. You’re still saving $36,400 on a single hire. This brings us to…

Total savings: $47,534

If you’re trying to cut cost, then hiring remote workers is definitely the way to go.

Higher Retention Rates (And Less Folks Who Quit On You)

The numbers don’t lie:

Companies which support remote work experience 25% less employee turnover than those which don’t support remote work.

Yes, yes, I know what you’re thinking…

But my office is going to be so awesome, and I’ve already ordered a whole gaming setup for our Chill Out corner. My employees will love coming to work!

But here’s the thing:

Job satisfaction doesn’t necessarily have to come in the form of a ping pong table, or weekly company-sponsored pub crawls.

Sure, those are nice perks, but are they more impactful than being able to work at home, and manage your own schedule?

It seems not.

According to statistics, employees who work from home report 25% lower stress levels, 73% healthier eating habits, 76% more company loyalty and 80% more work-life balance.

So save your money, and don’t waste it on pimping out your office.

All things being equal, your employees would rather work from the comfort of their own homes!

Access To Higher Quality Talent (AKA The Cream Of The Crop)

When you start hiring remote workers, this gives you access to higher quality talent.

Let’s take the previous example, and run with it.

Say you’re hiring a software developer.

According to the guys over at Business Insider and HackerRank, here are the top 10 countries with the best developers:

  • China
  • Russia
  • Poland
  • Switzerland
  • Hungary
  • Japan
  • Taiwan
  • France
  • Czech Republic
  • Italy

And here’s a map that represents this visually:

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Notice something? Yup, the good ole U.S. of A isn’t anywhere on that list.

So, you have two options:

  1. Stubbornly stick to hiring locally, and pay more for less capable employees, or…
  2. Recruit remote workers to your team, and get more bang for your buck

I know which one I’m picking! 😉

Diversify Your Team (And Watch As Effectiveness Skyrockets)

Okay, so we  just talked about fact that hiring remote workers gives you access to higher quality talent. Individually, each employee brings more to the table.

But on top of that, having a team made up of people with different cultures and backgrounds also brings about other benefits.

According to this McKinsey report, companies in the top quartile for ethnic and racial diversity in management were 35% more likely to have financial returns above their industry mean.

Studies also show that diverse teams…

All aboard the remote workers train?

Awesome. I’ll throw one last resource your way (this article on how to support workplace diversity)… and let’s move on to talking about where you can find your remote employees!

Where Are All The Remote Workers At?

There are a few popular websites where freelancers and remote workers congregate at, including…

Upwork, Fiverr, PeoplePerHour, Freelancer, and 99Designs.

The first thing you’ll want to do is create a (free!) account.

If you’re using platforms such as Upwork, go ahead and post a job description, and wait for remote workers to send in their proposals.

On some other platforms (such as Fiverr), you’ll have to sift through the “Gigs” that remote workers are offering, and decide who to hire based on this.

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On top of checking out these platforms, do also ask your entrepreneur friends if they have anyone they’d like to recommend.

If your friend is personally vouching for a remote worker or freelancer, then they must be awesome at what they do!

Writing A Kickass Job Description To Attract Talent


Not all job descriptions were made equal.

Here’s a negative example:

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If possible, link to your website so that your candidates have a better idea of what your company does. If you’re concerned about privacy, at least share what industry you’re in.

On top of that, don’t use vague terms such as “food plans”. I literally have no idea what this means – does it refer to a recipe book? Or a 7-day diet guide?

Here’s a positive example:

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This job description does a good job of detailing the advertiser’s expectations, including:

  • Topic / scope
  • Technical specs (word count, in this instance)
  • Working hours during which the freelancer should be available

A general rule of thumb:

When it comes to job descriptions, more is more.

Of course, I’m not saying that you should include irrelevant information…

…but the more clearly you communicate your requirements, the easier it is for your remote worker to live up to your expectations.

So make sure you include a comprehensive outline of your specifications and requirements, and steer clear of any terms which are ambiguous or subjective!

Include Reference Material

Let’s say you state in your job description that you want your website to be “colorful”. Everyone defines “colorful” differently, so you might get this:

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When what you actually wanted was this:

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Okay, that’s a tad dramatic, but you get what I mean.

Instead of simply saying you want a “colorful” website, and expecting your designer to read your mind, here’s what you should do:

Give your designer the specific RGB color codes of the colors you want to be on your website, and tell them which sections/elements to incorporate these colors in.

Also, provide your designer with more material to look at. In your job description, list 3-5 examples of websites you like, so that they can use these as a point of reference.

Weed Out Canned Responses

If you use one of the more popular platforms (such as Upwork, which has over 12 million registered freelancers), you’ll probably be bombarded with a gazillion proposals for every job ad you put up.

Most of these, unfortunately, are canned or template responses.

To be able to sift through these easily, some advertisers like to include “Please start off your proposal with “I love ice cream” (or something along those lines!) in their job description.

Personally, what I like to do is to ask a question that’s relevant to the task at hand.

For example, if I’m hiring a marketer to handle my Facebook ads, I might ask how they’d stretch a $10 ad budget.

If I’m hiring an SEO specialist to optimize my website, I might ask how they keep themselves updated about Google’s latest algorithm changes.

If someone responds to your job post, and doesn’t answer your question, then you can be sure that you’re getting a cut-and-paste proposal. Just trash those immediately!

Cool, you’re now an expert at writing an effective job descriptions.

Now, onto the next step… screening and evaluating your candidates!

Screening Candidates: Separating The Wheat From The Chaff

In every context or situation, there’s the good, the bad and the ugly.

The same goes with remote workers.

On one end of the spectrum, you have the ones who:

  • Have an amazing work ethic
  • Always deliver work on time
  • Consistently submit great quality work
  • Require minimal coaching and hand-holding
  • Are proactive and take initiative
  • Can think a step ahead and anticipate your needs

Basically, they’re a dream to work with.

But on the other end of the spectrum, you have the ones who:

  • Overpromise, and underdeliver
  • Don’t adhere to deadlines
  • Are unresponsive and hard to reach

I mean, I’ve even heard of freelance writers plagiarizing other people’s work. It’s that bad.

So once you get all your proposals or replies, the next step is to screen them, and narrow it down to your best candidates.


Like I mentioned above, the first step should be to filter out all the copy-and-paste proposals.

Next, get in touch with the remaining candidates, and start interviewing them.

Interview Questions To Ask Remote Workers

There’s really no hard and fast rule when it comes to interviewing, but I like doing video interviews as opposed to phone interviews.

In order to get the best fit for your team, you’ll want to learn as much about your remote worker as you possibly can… and I find that video interviews are more conducive to this!

Questions to ask in your interview include:

  • What is your longest-standing client account?
  • Are you freelancing on a part-time or a full-time basis?
  • Can you meet my deadline?
  • How do you approach your projects?
  • What type of clients do you like to work with?
  • Do you have any questions about the project?

Ideally speaking, you should be working with someone who’s freelancing full-time, and has long-term retainer clients.

If your candidate is doing this on a part-time basis, they might be less responsive to your messages (they’ll spend a large portion of their day on school or their full-time job, after all).

And if your candidate doesn’t have any long-term clients? This might be a red flag that indicates that they aren’t consistent with the quality of their work.

Next, it’s also important to clarify if deadlines are reasonable and doable.

If you’re interviewing a remote worker from a different country, be sure to specify the timezone that you need the work delivered by.

For those hiring for technical jobs, do also ask your candidate to explain their process or approach.

A site migration project, for example, will involve:

  • Determining the scope and objectives
  • Identifying risks
  • Reviewing wireframes
  • Benchmarking your legacy site’s performance, and
  • Pre-launch testing

…and those are just the tasks that need to be done before the site migration is carried out.

If your remote worker can rattle these off easily, that’s a good sign.

If they reply with a blank stare and an “Um, just tell me your requirements and I’ll do it”, then go ahead and strike them off your list.

Last but not least, ask your remote worker what type of clients they like to work with, and if they have any questions about the project.

At the end of the day, you want to help your remote worker do their job well.

If your worker tells you that they have difficulty working with micro-managing clients, then remind yourself to not check in with your worker unless it’s necessary!

For more strategies on hiring remote workers, check out Hubstaff’s infographic.

Looking At Past Feedback & Portfolios

Regardless of what platform you’re on, you’ll probably be able to access information about how highly your candidate is rated, and how many jobs they’ve worked on.

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If you’re hiring on Upwork, for example, you’ll be able to see your candidate’s Job Success rate, as well as:

  • Their hourly rate
  • The total amount they’ve earned
  • The number of jobs they’ve worked on, and
  • The number of hours they’ve worked
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Scroll down a little further, and you’ll see a “Work History and Feedback” section, which contains reviews from your candidate’s past clients.

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Have a look, and use these reviews to corroborate whatever your candidate has told you.

Further down, there’s also a “Portfolios” section, where freelancers can showcase some of their best work. Check this out as well!

How Much Should I Pay My Freelancers?

If you’re new to hiring remote workers, deciding how much to pay per hour or per project can be pretty tricky. Use the following tips to determine your pricing structure and budget!

Per Hour Jobs VS Fixed Price Jobs: Which Is Better?

If your project is still very much a work-in-progress, and there’s a high chance that the scope might grow or lessen further down the road, then consider going with an hourly project.

The question then arises:

How do you make sure your remote worker is actually working when they say they are? Or in other words, how do you know you’re not getting fleeced?

Well, most freelance job platforms come with tools that will allow you to monitor your remote workers’ progress.

With Upwork, here’s how it works:

Your remote worker downloads the Upwork Desktop App. Once they log on and indicate that they’re working on your project, the app will automatically capture screenshots of their screen every so often.

At the end of the week, you’ll be billed for the number of hours your remote worker has clocked. If you’d like, you can access your remote worker’s Work Diary, and review the screenshots that were taken throughout the week.

On top of that, there’s also an option for clients to set a weekly limit on billable hours. This acts as another safeguard!

Okay, on to fixed price jobs.

If you’ve already nailed down the specific deliverables of your project, and you know the scope won’t change too much, then a fixed price job might be the right fit.

One advantage of fixed price jobs? If your remote worker turns out to be an extremely slow worker, this won’t inflate the total cost of your project, and bust your budget.

Right, now that you’re up to speed on per hour jobs vs fixed price jobs, let’s move on!

Determining Your Budget (Without Plucking A Number Out Of Thin Air)

How do you determine your project budget?

To start off, think about how much hiring a full-timer would cost you.

According to HR company Randstad, salary prices range from:

  • Web Developers – $55,500 to $110,000
  • Social Media Managers – $49,000 to $90,000
  • SEO Specialist – $49,500 to $90,000
  • Graphic Designers – $32,000 to $75,000

Now, let’s break this down into an hourly rate, which would give us:

  • Web Developers – $26.68 to $52.88
  • Social Media Managers – $23.56 to $43.27
  • SEO Specialist – $23.80 to $43.27
  • Graphic Designers – $15.38 to $36.06

You can look at this as a baseline of sorts, but you’ll probably be paying a little more than what you see here.

Why? Remote workers don’t get the same benefits that full-time employees do, so their hourly rates are generally higher to compensate for this.

If you’re using Upwork to hire, they’ll also provide you with a range of budgets for reference.

For software developers, for example, Upwork says that you can expect to pay:

  • <$20/hour for entry-level developers
  • $20 – $40/hour for intermediate developers, and
  • >$40/hour for expert developers

If you’re looking at web research assistants, on the other hand, your budget should be around:

  • <$7/hour for entry-level assistants
  • $27 – $18.50/hour for intermediate assistants, and
  • >$18.50/hour for expert assistants

Last but not least, your budget also has to take your criteria into consideration.

Let’s say you own a website about diet and nutrition, and you’re looking for a writer to contribute to your website.

Are you just looking for a writer who can emulate the tone of your website, and deliver a compelling article, or are you looking for someone who…

  • Has a degree in nutrition, or a related field
  • Has worked with clients in the same field
  • Can produce articles on a short turnaround time (<48 hours)
  • Can also design your article cover photo

If you’re leaning towards the latter, then it goes without saying… you’ll have to increase your budget!

Psst: if you’re trying to build an app, read this article to find out how much it’ll cost. If you want to set up a website from scratch, check out this other article.

Cheap, Fast, and Good: Pick Two

When you post your first job, and you start looking through all the proposals that you receive, you’ll probably feel like you’re a kid in a candy shop.

Oh my god, my initial budget for this press release is $100, but this guy is offering to do the job at just $50.

Then, two minutes later…

Holy cow. This is INSANE. This other applicant says that he’ll write the press release for $3. That’s THREE. DOLLARS.

Trust me: your mind will be blown.

You might even feel like kicking yourself for not jumping on the bandwagon earlier. If it’s that cheap, you might as well outsource every damn thing, right?

Remember this, though: you get what you pay for.

Yes, there are wage differences across the globe, but some freelancers will offer to do work at rates which are suspiciously low.

If you commission someone to code a website for $5, you’ll probably end up getting a template with a few tweaks, instead of a custom-built site. (Scratch that, you’ll definitely get a template.)

So don’t be taken in!

Also, consider the impossible trinity of Cheap-Good-Fast.

This animation says it all. Yes, remote workers and freelancers are often more cost-effective than traditional employees, but they’re not robots.

Want it cheap and good? It’ll be slow.

Want it cheap and fast? It won’t be good.

The bottom line: you can’t have your cake and eat it too!

The Trial Period (Test-Drive Before You Commit!)

So you’ve narrowed down your list of options to two or three candidates.

Don’t get ahead of yourself, and offer the job to someone immediately. Instead, get each of these candidates to do a paid trial for a month or so.

Now, I know that some business owners might like to hit the ground running.

You’ve got a ton of things you want to get done, and you want your company to be agile and quick to roll out changes.

At the same time, you figure: if you commission a few projects right off the bat, you might be able to get your remote worker to agree to a cheaper hourly rate or fixed price.

But here’s the thing:

Just like you wouldn’t buy a car without test-driving it first, hiring a remote worker without working with them on a trial project is not a good idea.

If you’ve deposited a large sum of money with the freelance platform, and you terminate the project ahead of time, it might be tough for you to get your money back.

Your remote worker might also leave you a negative review (yup, this review thing works both ways!)… and this might make other candidates less open to working with you.

So take your time in getting to know your candidates, and only commit to a long-term project when you know they’re The One.

To learn more about setting up a trial for your remote worker, check out this guide by Upwork!

How NOT To Manage Your Remote Team

I know I’ve waxed lyrical about working with remote teams, but like anything else, this comes with its own set of challenges.

To work well with your remote team, and make the process as painless as possible, steer clear of these common mistakes!

Having Multiple Points Of Contact (That Shit Is Confusing)

Whenever possible, have a single point of contact who’s liaising with your remote worker.

If you have two managers who are working on a single client account or project, and they both need to be able to reach your remote worker, then you’ll have to proceed with caution.

When you have two managers who aren’t on the same page, and they’re telling different things to your remote worker, that’s a recipe for disaster. So make sure your managers iron out all the project details before speaking to the remote worker!

Giving Too Little Direction (Your Guidance Is Needed!)

Look, just because you’re hiring a remote worker doesn’t mean you can get away with not onboarding them or welcoming them to your team.

If you want your remote worker to be an effective employee, you’ll need to invest some time into them. Tell them about your company and its culture, and communicate rules and expectations.

Here’s a smart way of doing this:

Draft an Employee Handbook that you can share with your new hires – this way, you can give them a quick 5-minute intro, and leave them to read up in their own time.

Your Employee Handbook may contain:

  • Information about your company, including your company’s mission and values
  • Job-related information (pay and benefits, employee guidelines, etc)
  • Your new hire’s Next Steps – should they create a Slack account and join your channel? How do they introduce themselves to the rest of the team?
  • And anything else that you might want to add!

If you need some inspiration, check out here are some awesome examples from Zappos, Netflix, and Nordstrom that you can have a look at.

On top of that, when you assign tasks to your remote worker, be sure to provide them with all the materials/info they need as well.

Pass them your sales manuals and style guidelines (if appropriate), and break down large projects into smaller, bite-sized milestones that they can tackle easily.

Delaying Payments (Don’t Be That Guy)

You might not be doing this purposely – maybe you’ve had an exceptionally busy two weeks, and you just can’t find time to pay your remote worker.

But here’s the thing:

If you don’t make it a point to pay your remote workers on time, this sends the message that you don’t value their work.

Worst-case scenario? Your remote worker gets tired of chasing you for payments repeatedly. They start putting out their feelers, and looking for other options. One day, they call you on Skype, and tell you apologetically that they’ll be quitting at the end of the month.

Best-case scenario? Your remote worker starts feeling anxious and insecure about their job. There are no implications in the short run, but in the long run, this might impact their motivation, which hurts your bottom line.

So always be prompt with your payments!

If you’re notoriously absent-minded, these bill reminder apps might do the trick.

Expecting Too Much (While Paying Peanuts)

I know I’ve said this earlier on, but it’s worth reiterating:

You get what you pay for.

If you’re hiring a $5/hour coder straight out of high school, you won’t get the same quality that you can expect from an expert software developer that charges $150/hour.

Also, I know of some people whose gameplans are to hire from developing countries (where you can get the cheapest labor). It’s not a good strategy, if you ask me.

Let’s say you hire a coder from Thailand, DESPITE knowing that their native language isn’t English, and despite seeing that their English proficiency is listed as “Beginner”.

Now, when it comes time to work on your project, you realize your coder can’t understand 80% of what you’re saying, and doesn’t have a clue what you want.

Whose fault is this?

Hate to break it to you, man… but it’s yours 🙁

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