How to Hire Your First Remote Team

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Working in a café

Working in a café

So you’ve decided to cut costs by hiring a remote team, or you’re a boss that quite literally likes to live like a boss in a beautiful remote getaway in the Maldives — either are applaudable choices and I salute you.

Managing a remote team is not as difficult as it sounds; in fact it’s been noted that remote teams are 35% more productive and 11% happier because of the lifestyle they lead, and under your management this could be your team. All you need to do is hire the right people!

Information sources: Hubstaff and Zenefits.

Post in Job Sites Aimed at Remote Workers

It’s not unheard of for job-hunters to send out their resumé to absolutely everybody that is hiring without really reading the job requirements. Posting your offer on job sites aimed at remote workers ensures that you’re targeting the right crowd.

Here are the best and most well-known job boards for remote workers (feel free to suggest some more in the comments!):

Ask the Right Questions During the Interview

It’s important to understand this first: a remote worker isn’t necessarily a freelancer, and a freelancer isn’t necessarily a remote worker. A remote worker lives far away from the rest of the team but can be hired as either a full-time employee or as a contractor, whereas a freelancer can only be a contractor but may live relatively local. It’s important for your hire to understand the unique challenges of working remotely.

Ideally, you should be a remote worker yourself so that you can understand and correctly explain these challenges; this ensures that you can effectively manage an employee that’s new to remote working, helping him/her gain experience with the concept.

Here are the questions you should be asking:

  1. How will you balance your home/work life?
  2. Is your timezone compatible with our team?
  3. Do/will you use collaboration tools?
  4. How will you remain accountable?
  5. How often will you move around? (Specific to digital nomads).

Provide Plenty of Support During Onboarding

If you’ve discovered a remote worker from the right crowd, and you’ve asked them the critical questions, and you’re satisfied with the answers that they gave, you’ve probably found yourself a remote worker who could be a smashing asset to your team — but not without careful onboarding. New hires have a natural desire to prove themselves, which they can’t do without the support of a manager or team leader. Without this support, your team is left in confusion, which leads to isolation and a lack of confidence.

Your team needs to know:

  1. Who they can turn to for advice
  2. Who they can turn to when there’s conflict
  3. What their work involves in the short and long term

With this level of support your team will remain happy, connected and confident in their abilities to collaborate when required and reach out for help when they’re feeling uneasy (as long as the support is maintained of course). For that to happen, your remote team needs to be using communication apps that facilitate openness and expression, and collaboration apps that inspire communication and team-wide problem-solving.

Let the New Hires Decide on the Tools

Since remote teams don’t converse face-to-face, they’re pretty much left to communicate and collaborate through app interfaces — and this is a good thing. Remote teams report that the inconvenience of timezones and lack of face-to-face communication results in fewer unnecessary/impromptu meetings and higher productivity. They found that instant messaging was faster, easier, more engaging and less time-consuming.

But which tools are the best? Many will argue that the best tool is the one that you know how to use well, and is effective for completing the task at hand. Personally, I think this is why deciding on the tools is the hardest step to take when building remote teams — everybody has their own opinion regarding tools.

It will require some trial-and-error at first, and almost definitely some compromise. The worst thing you can do at this stage is refuse to accept when communication is breaking down or a certain tool is hindering the workflow. Accept failure, try something else, and move on from it; think of it as lessons learned, not time wasted. Refinement is the key — this is why apps and services let you abuse free trials for a limited time.

For specific tips on collaboration, communication and tools, read my 10 Tips for Collaboration article.


If you’re still not sold on the idea and you need the cold, hard facts about remote working, then this research report by Hubstaff explains exactly why 65% of employees would prefer to work remotely. Note: it has nothing to do with pay or fewer hours!

Hiring the right guys and creating an optimal remote culture for the team could be the best decision your company ever made. Once you’ve decided to hire your remote team, Time Doctor has a list of 10 Mistakes To Avoid When You Scale Your Remote Team.

Have a question of concern? Voice it in the comments!

Daniel SchwarzDaniel Schwarz
View Author

Previously, design blog editor at Toptal and SitePoint. Now Daniel advocates for better UX design alongside industry leaders such as Adobe, InVision, Marvel, Wix, Net Magazine, LogRocket, CSS-Tricks, and more.

entrepreneurshipjoelfmanagementremote teamsremote workstartups
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