Recruiting Remote Freelancers Is Difficult

recruit and interview remote workersThere’s no way to beat around the fact that hiring remote freelancers is a difficult task and takes repetitive practice. Today, I’m going to teach you how to recruit and hire remote freelancers from the comfort of your office.

You first have to figure out the best places to find and recruit the remote freelancer you are looking for then you have to walk them through a detailed interview process to make sure that they have the skills to perform the tasks that you need completed.

Most of the time, applicants will be on different time zones so you also have to make sure that you set a time that works for both you and the applicant. Finally, you have to make an educated decision based off of a couple of conversations that you have had with the person determining whether they are a good fit for your company and the role.

That’s quite the gambit of tasks while you’re also trying to run your business. 

Luckily, I’ve had over 4 years of experience performing these tasks and I can point you in the right direction when or if you decide to recruit and interview remote freelancers on your own.

Step 1: Define Exactly Who You Want

There are thousands of remote freelancers looking for new positions everyday. As a business owner, you have an endless pool of applicants that are willing and able to take on your task.

However, not all of them are going to be the perfect fit. In order to optimize your time, you must define exactly who you want for the role that you are hiring for.

Here’s a few areas to get started and to clearly define your expectations.

  • Specific skill set, i.e. advanced macros in Excel
  • Number of years with that specific skill set, i.e. over 3 years
  • Number of hours working as a remote freelancer, i.e. over 1,000 hours in the past year
  • A schedule that you prefer, i.e. working when I am on during the day
  • Preferred rate, i.e. $5.00/hr to $15.00/hr
  • Level of English, i.e. Native
  • Start date, i.e. in the next 2 weeks
  • Country of residence, i.e. Philippines
  • History with previous clients, i.e. over 10 positive reviews from past clients

When you narrow in on the exact freelancer that you are looking for, it becomes much easier to say “no” to applicants that don’t meet that criteria. Don’t be afraid to say “no.” Like I said, there are plenty of fish in the sea and they are hungry.

Step 2: Create and Publicize Your Job Posting

Using your characteristics from Step 1, I recommend creating an in-depth job posting that outlines your ideal candidate, introduces the reader to your company, and tells the reader about the purpose of the role in the company.

Perform research and choose the platforms where you want to recruit based off of the type of job that you are looking to fill. Once you’ve decided, create an account and post the jobs to the public.

As applicants roll in, compare their information to your ideal candidate checklist. If there are too many inconsistencies, don’t waste your time. Keep searching and keep reading new applications until you find the best ones.

Step 3: Interview At Least 5 Applicants

Once you’ve collected enough applicants that there are 5 strong candidates, set up interviews with each of them. For the interview process, split it up int 3 different stages.

  1. Information
  2. Skills
  3. Personality

Depending upon your time, you can split these into 3 separate meetings or you can do it all in one. If you decide to split it up, make sure to have the meetings within a relatively close window of time. You don’t want to forget about the applicant’s first meeting because of the passing of time.

  1. Information

    In this stage of the interview, go through your ideal candidate checklist and make sure that they meet all of your key criteria. If they can’t meet a number of characteristics that you’ve deemed a deal breaker, move onto the next applicant. Don’t waste your time on an applicant that simply won’t work out.

  2. Skills

    If the applicant meets your key criteria, talk to them about their skill set. Ask them to describe their expertise and how long they have been practicing the particular skill you are looking for. If they seem to know what they’re talking about, ask them more specific questions about how they would handle different task-related scenarios. If the applicant does not seem to excel in the exact task you are looking for, move on.

  3. Personality

    If the applicant appears to have the skills that you need, move onto the final step of getting to know them a bit more personally. They are someone that you could potentially be working with for a long period of time. This stage can make sure that the applicant is reliable and will be a good long term hire.

You can ask questions such as:

  • What are your goals as a remote freelancer?
  • What is your greatest strength and weakness?
  • How long do you expect to work with me?
  • How do you handle communication about emergencies and being late?
  • Do you have any other long term clients?

Don’t Settle for the First Applicant

If the applicant can make it through these 3 stages, there’s a strong chance that they will be a strong remote freelancer for your business.

Take the time to find the right freelancer and don’t settle for the first one that starts to meet your needs. At the end of the day, there is no guaranteed way to always hire a rock star. However, if you play your cards right, you have a much better chance of hiring a strong remote freelancer.


Connor Gillivan


Connor Gillivan is the author of Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies, a serial entrepreneur, and the CMO and co-founder of When he’s not bringing together hundreds of freelancers and business owners, he’s mentoring entrepreneurs through his site, He currently lives in Denver, Colorado.


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