How to Hire A-Player Remote Workers (And Keep Them Happy)

Despite the potential distractions in theory, studies have shown that employees are more productive when working at home. A little surprising, right?

With more and more Americans working remotely, many companies are begin to catch on. A remote team might be better than having an actual office.

Of course there may be disadvantages to having a remote team. Communication is more difficult, you have less face-to-face time and it’s a little more difficult to manage your team.

So why would you want to hire someone to work remotely?

The results of remote working have been favorable.

For example, remote workers work 9.5% longer and are 13% more productive. They’re also judged to be happier and their quitting rates are also cut in half. Compared to office employees, remote workers are more engaged. An engaged employee is what you want, right?

Besides productivity, you can cut overhead operational costs. If you decide to go 100% remote, you can forgo an office headquarters altogether. If you’d still prefer to have an office for employees nearby, you can reduce office space, which amounts to saving about $2,000 per employee every year.

working at home

And it’s clear why. The cost-benefits of hiring remote workers are tremendous for business owners. Look at these stats:

  • Over two-thirds of employers report increased productivity among their telecommuters.
  • AT&T workers work 5 more hours at home than their office workers
  • American Express workers produced 43% more than their office based counterpoints
  • Nearly six out of ten employers identify cost savings as a significant benefit to telecommuting.
  • IBM slashed real estate costs by $50 million.
  • McKesson saves $2 million a year.

Hiring employees is time- and energy-consuming and we’ve previously discussed the general process of hiring effective employees. Now we’re going to explain how to specifically hire a remote team.

Before I get into that, I want to make a distinction between remote workers and virtual assistants (I’ve seen some people use the terms interchangeably). Here’s how I define them:

A remote worker, from my perspective, is someone that works full time for you and that person is usually domestic, speaks your language and is someone that you would expect to hire full time face to face. It’s likely someone that you can hire locally, the only difference is that they’re working from home.

A virtual assistant, from my perspective, is someone that is working from out of the country, a common country is the Philippines. It doesn’t always have to be this way, virtual assistants can be based in your respective country as well.

We’re going to focus on hiring remote workers.

It’s important to do the first three things here before you begin searching for remote workers. You’ll see why.

1. Make your internal documentation solid.

Without proper internal documentation–or as I like to call it, an internal wiki–the onboarding process will get messy.

Say you hire the person and give them a project, but they have dozens of questions about what tools to use, who to ask for questions, who to report to, where to find certain company information, and so on. You probably don’t have time to answer all those questions.

By putting together your internal wiki, you consolidate all the necessary information for new hires into one convenient location. This information may include company information and processes, core values, communication processes, detailed explanations on how to do certain projects, and so on. We like to use Hackpad for all of Single Grain’s documentation.

You can also create screencasts to show exactly how to perform a task. You can create screencasts using services like Screenflow or Camtasia (you can also just do a Google search for “free screencast app”).

With these documents handy, you can simply send over the documentation to a new hire to review. You don’t need to take the time out of your work day to explain everything (though you should still make yourself available to answer any questions or further explain things).

It’s better for you to have this prepared before beginning the hiring process so you won’t need to stress about onboarding when you have a new hire. It’ll save you the time and headache.

communication tools

2. Make sure your communication system is on point.

If it’s your first time hiring a remote employee, you may not yet have a thorough communication system for such a team, but you should have communication tools set up and ready to use.

It’s important to also clarify what situations to use each communication tool for. Here’s how we use our different communication tools at Single Grain:

  • Trello: Used to manage temporary projects that require multiple steps or action items across multiple teams or people.
  • Basecamp: Used for external project management, client communication and delivery of client documents. ALL client communications should be sent through Basecamp.
  • HipChat: Best used to touch base with team members quickly about projects, share links or small files, or to ask easy questions that can ideally be answered with a ‘Yes’ or ‘No’
  • Skype: Best for 1 on 1 conversations that may require screen or file sharing. Longer conversations with more complex answers or collaborative problem solving.

Depending on urgency:

  • Red Alert: Such as an angry client about to cancel, big mistake, someone’s hurt. Use HipChat Video, Phone Call with business phone system features that bring everything under one platform to help streamline your operations or Google Hangout to get an immediate answer
  • Yellow Alert: Such as difficult question you can’t answer, need help hitting a deadline, request for something we can’t do. Use HipChat or text message to get an answer within the next couple of hours.
  • Green Alert: General questions, ideas, project updates. Use Trello or email to get an answer within the next day or two

This may seem trivial, but you don’t want an employee to send an email in an urgent situation–you never know when you’ll see the email. Likewise, you may not want to have an employee calling you every time he has a question.

Whether it’s project management or communication, be explicit in how each tool is used. This way, your new hire can get caught up to speed and jump in and understand how to communicate properly right away.

Now that we have those things out of the way, let’s start with your hiring process.


3. Have a clear job description.

This seems obvious to do, but you don’t want to screen through resumes and applications, get on a call with an applicant and then tell them the job is remote. He might be turned off by it and remove himself from the hiring process. And you would have wasted your time looking at his application and blocking out time in your schedule to meet with him.

Make sure your job description clearly states that the job is remote. If you’re talking to recruiters to help you with hiring, make it clear that the position is a work from home position.

Some people don’t work as well remotely while others thrive on it. Their preference is completely independent from their qualifications and work experience. You want to make sure the right people are responding to your job listing so no one wastes their time.

4. Find quality hires.

Now you have a job description, but how do you reach out to quality remote workers? How can you trust that they’re hard working?

Here are a few ways Wade Foster of Zapier suggests to increase your talent pool.

  • Reach out to your networks. People you’ve worked with in the past could be great options for hires. Or you can ask friends and family to ask around.
  • Ask your current employees for referrals or to help with sourcing
  • Join local meetup groups
  • Create a blog post that’s relevant to hiring and mention that you’re hiring (Buffer does a good job of this)
  • Post the position to job boards
  • Share the job listing on your social networks

5. Know what characteristics you’re looking for.

This is different from the job description because, while a person that fits the job description can perform the duties, it doesn’t mean they’re a fit for your team.

Since the person will be working remotely, making sure that they fit your company’s core values is all the more important.

“The true test of a man’s character is what he does when no one is watching.” ― John Wooden

You won’t be watching over this person’s shoulder at all. There aren’t many other ways to determine how engaged the person will be at work unless if you know what their core values are.


6. Consider their location.

This goes back to the importance of communication. If the time zone difference is extremely large, then direct communication will be that much more difficult. You might send a message at 9am on HipChat and get a response 8 hours later when the other person wakes up.

However, this is also something to discuss with the applicant. If you both can agree on a proper way to keep communication working smoothly with the rest of the team, then great.

7. Do a video interview.

I highly suggest a video interview over a phone interview. Body language is as important as what the person actually says. By holding a video interview, you can see the applicant’s expression when you ask a difficult question.

You can see how excited the applicant gets when she explains why she wants to work for you. Or you can see how she holds her posture as she answers your questions, or if she’s slouching.

These may not be large determining factors in the end, but you can get a deeper understanding of their character.

8. Ask the right questions.

Out of the thousands of interview questions you can ask, for a remote worker, there are a few specific questions to ask.

  • Have you had experience working remotely before?
  • How do you work alone?
  • What’s your ideal type of working environment?
  • How much of your social life comes from work?
  • Tell me about a situation when you dealt with conflict in the workplace.

Someone who has worked remotely before has probably proven themselves capable of working remotely.

Someone who works remotely will be alone most of the time and won’t have the pleasure of walking to someone else’s desk to strike up a conversation. There is almost no social aspect to remote working. If the applicant has a social life outside of work, they will be much happier.

put up barriers

9. Put up barriers to find the serious applicants.

You’re always going to receive applicants who just want a job and apply for dozens or hundreds of jobs a day. By putting up barriers, you make sure that you only spend time and energy on the people who are serious about working with you.

I like to give applicants a homework assignment. For example, if it’s for a marketing position, I’ll may ask them to come up with a content promotion strategy. If it’s for sales, I’ll have to come up with a list of 10 prospects and create a screencast to explain how they did it.

These are simple assignment,s but they require some thought and gives them an idea of what they’ll actually do if they get the job.

10. Put them through a trial period and know what you’re looking for.

If the applicant gets through the interview process and knocks down all the barriers you’ve put up, and you decide you want to hire them, you should put them through a trial period first.

With the homework assignment, they were on their own to complete a small project, and you were able to determine whether or not they have the skills. However, with a trial, they are actually working with you and your team for a short period of time (say a week). You can get a good idea of whether the person works well with your team or if you’re about to hire an asshole.

Use the trial period to look for a culture fit.

It’s important to note that you should pay them as they go through this trial period as if they’re an actual employee.

11. Create a healthy remote working culture.

Now, even though you might’ve hired them, the work isn’t over. You have to keep them happy working with you.

Because your team is dispersed, it’s all the more important to build team culture.

Zapier does this by using Sqwiggle and Google Hangouts regularly so there is always face-to-face interaction.

At Single Grain, our employees receive perks like complimentary Spotify Premium or Oyster Books subscriptions through Uncover.

Is it okay for your team to be open about personal problems? Or to send funny pictures on Slack? Should your team only talk about work related things or do you want a more relaxed communication style?

host workcations

12. Host quarterly workcations.

The concept of a workcation is relatively new and with working often taking up more time out of our lives, people often don’t take vacations or feel deprived of vacations.

For remote workers, without the structured day of a 9-5, it’s easy to end up overworking. And even though your team may have an awesome online culture, it’s better to meet face to face and build an in-person relationship.

Hosting a workcation will help to create a healthy work culture for your team. At Single Grain, I host a workcation for my team once a quarter to make sure they’re not burning themselves out.

If you don’t believe in workcations, companies like Uber and WeWork have had tremendous success with them.

By traveling and spending time together, your team can rejuvenate, strengthen bonds among team members and travel. This results in a happier work culture.

You can host a workcation wherever you please–another country, another state, or even just another city.

Here’s how you can organize a workcation.


It’s clear that that hiring remote workers has numerous benefits. The difficult part is finding and hiring A-player remote workers.

Our entire team at Single Grain is remote and we’ve had a great experience working with each other, keeping each other accountable and getting things done. So it’s possible!

The most important part is making sure that your documentation and communication systems are in place before bringing on remote workers. With those two things ready, you can jump right into the hiring process.

What’s your #1 tip for hiring remote workers?

More hiring resources:

Image sources: Death to the Stock Photo, Housing

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