String’s Guide to Hiring Remote Workers

(without Losing Your Shirt!)

String Nguyen
ART + marketing
5 min readMay 8, 2018

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By now you’ve heard that hiring remote workers is vital to outsourcing processes that you don’t enjoy or don’t have the skills to complete. Books like The 4-Hour Workweek make it sound simple. Stuff your work off to a virtual assistant and kick back on the beach! But if you’ve ever tried to give a task to a virtual assistant, you know that it’s not as easy as it sounds.

Perfectionism is a problem for many entrepreneurs, so delegating tasks to anyone else, let alone a new remote worker, is hard. Furthermore, finding someone whose talents and communication skills mesh with your own is even harder still.

I’ve done a lot of outsourcing over the last few years and would like to share some tips with you about how to do it properly — without losing your shirt!

Always have a trial run

The first stage in hiring a remote worker is to give them actual, usable, paid tasks. Hire them and use their work. Don’t give them a test task, just be honest and tell them that it’s a limited engagement but that their work will be customer-facing.

During the test run, you’ll have a few goals. The first is to see if your communication styles are compatible. You’ll also want to show them how to use your tools and see how they set (or don’t set!) processes in place. Finally, you’ll want to gauge the quality of their output.

When you give that first job, be sure to think up several useable outputs typical of work they’d be doing in the future. So, for example, if you were hiring a video editor you might ask for:

  • A video introduction suitable for YouTube, and provide some necessary digital assets
  • Cut a video to a certain length, add subtitles, and create a style guide for future use

Always be sure to give more than one task, so that you can see the scope of their talent.

Step 1: The Video Call

During the first stage of the trial run, you’ll want to set a date to have a Zeen video call. Do your best to convey the job tasks in clear, concise language. You aren’t testing them; you’re giving them a real job, so be sure to give thorough instructions as you would for any employee.

Listen carefully. You want them to ask questions when you aren’t clear, but not the same questions over and over. So be sure to take note of what you have and haven’t had to clarify.

You’ll also want to assess how comfortable you feel working with the remote worker. If you’re getting alarm bells just because you feel like the other person is making you uncomfortable, don’t be afraid to listen to your inner voice. You’re looking for someone with whom you can have a comfortable working relationship.

That means someone you’d feel comfortable cracking a joke around. Also be sure that they don’t interrupt you. That gets old, fast.

Step 2: Tools, Tasks, and Processes

After you’ve introduced the task, it’s time to rope your remote worker into your toolset and work process.

For my projects, the toolset that I tend to use is:

  • Toggl — for recording time worked
  • Zeen — for video conferencing and recording audio
  • Trello — for project management and keeping notes
  • Google Drive — for keeping a shared folder of documents and research

It’s okay if your remote worker hasn’t used your toolset in the past. They should, however, be willing to try your system out. Just the same, if the toolset doesn’t work for your remote worker, but their product is stellar, you should be open to change as well.

I like using Zeen, as it allows you to set the agenda. After the meeting, an audio recording is sent to your email that tracks your audio. There have another feature that allows you to have a to-do list and create action items.

Agendas can be set with Zeen video conference calls.

One important thing to watch for is whether your remote worker is starting to develop a process for future tasks. If they cannot reuse any of the work they’ve done at the end of your project, it’s a warning sign.

Step 3: Evaluating The Product

When you evaluate the product, don’t only look at the quality of the output. You also want to be sure that the process is something that can be done again, faster the second time.

Also think back on your communication throughout the task. Were there any questions that they didn’t ask in light of the final product? Did they ask the same question multiple times and still get something wrong?

Finally, did they follow up? Was the product delivered on time? Did they take ownership throughout the project?

There’s a lot more to finding a good remote worker than finding someone with talent.

Dancing is a great way to break momentum

Personality Traits to Seek in a Remote Worker

Open-minded — You want a remote worker that listens to your suggestions. Of course, if they give honest feedback on those suggestions, that’s even better, but they should at least consider your input.

Curious — A remote worker who is always looking for a better solution, trying new tools, and learning new things is a gem to treasure!

Efficient — You want to find someone who has a system, uses processes to complete even small tasks, and keeps track of time well.

Proud — Your remote worker should have pride in their work and be an up-and-comer in their field.

One Final Note for Entrepreneurs

If you’re having trouble finding a remote worker, don’t necessarily despair. Usually, I go through 3–5 remote worker trials before settling on one.

However, if you are not able to find someone within that number of trials the problem could be you!

Like I said earlier, entrepreneurs, especially freelancers and solopreneurs, tend to be perfectionists. You’re looking for someone to take ownership of your tasks, so be sure to look back at the tasks you’ve assigned to see if you were micro-managing.

Do not micro-manage.

Micro-managing your remote workers is the number one reason that entrepreneurs screw up their remote worker relationship. Be sure to grant your remote worker creative control.

Signs you might be micro-managing:

  • You ask for a minor switch in the font, for something to move up 10 pixels, or for a color to be slightly darker
  • You ask why they did it how they did it more than once, or after they’ve established a process
  • You check-in more than once a day

I hope that this has given you a good idea of how to hire remote workers. Please let me know if you have any questions! I’m a tweet away with “@stringstory”

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String Nguyen
ART + marketing

Video is my thing and I like fried chicken — I do better on Linkedin linkedin.com/in/stringstory